20 Movies Like There's Something About Mary | Similar-List

Directed by Peter and Bobby Farrelly, There's Something About Mary (1998) is a romantic comedy that transformed the genre with its brilliant mix of humor, charm, and unforgettable characters. The story follows Ted Stroehmann (Ben Stiller) as he tries to reconnect with his high school crush, Mary (Cameron Diaz), resulting in a whirlwind of hilarious mishaps and quirky encounters. This film's skillful blend of heartfelt moments and outrageous comedic situations has cemented its status as a beloved classic. We present a curated list of entertaining movies that echo its themes and comedic style. Each recommendation embodies the spirit of There's Something About Mary, making them ideal choices for those searching for laughter, love, and unforgettable moments.

20 Movies Like There's Something About Mary

1. Forgetting Sarah Marshall (2008)

Directed by Nicholas Stoller, Forgetting Sarah Marshall tells the poignant and hilarious story of Peter Bretter (Jason Segel), a struggling musician who is heartbroken after his girlfriend, Sarah Marshall (Kristen Bell), abruptly ends their relationship. Devastated and seeking to escape his memories, Peter embarks on a trip to Hawaii, hoping to heal. However, his plans take an unexpected turn when he discovers that Sarah is vacationing at the same resort with her new boyfriend, the famous rock musician Aldous Snow (Russell Brand). This setup leads to a series of awkward and comedic encounters that force Peter to confront his emotions and redefine his sense of self.

The film showcases an impressive ensemble cast, including Jason Segel, who co-wrote the screenplay, and Kristen Bell as the enchanting yet elusive Sarah. Russell Brand delivers a breakout performance as the flamboyant Aldous, adding a layer of comedic flair to the narrative. The chemistry among the cast is palpable, with standout performances from the quintessentially awkward, lovable supporting characters, including Mila Kunis as Rachel, the hotel concierge who becomes a source of unexpected support and romance for Peter.

Upon its release, Forgetting Sarah Marshall received widespread critical acclaim, particularly for its blend of humor and heartfelt moments. Critics applauded Jason Segel's authentic portrayal of vulnerability, noting that his relatable performance brings depth to Peter's character. The film not only resonated with audiences but also performed well at the box office, grossing over $105 million worldwide. It has since been recognized as a modern classic within the romantic comedy genre.

The film made a significant cultural impact, particularly in its candid portrayal of heartbreak and healing. By addressing themes of emotional vulnerability and self-discovery, Forgetting Sarah Marshall resonates with anyone who has experienced the challenges of moving on from a past relationship. It helped pave the way for the resurgence of ensemble romantic comedies in the late 2000s and early 2010s, showcasing the potential for blending humor with deeper emotional narratives.

The film artfully navigates themes of love, loss, and personal growth, all while delivering gut-busting humor. From Peter's comic misadventures at the resort to his hilarious encounters with Aldous, the film uses wit to explore the awkwardness of moving on. Memorable comedic moments, such as the famous puppet musical that Peter performs to express his feelings, illustrate the film's clever use of humor to address serious topics. It ultimately emphasizes the importance of self-acceptance and the healing power of friendship and new love.

Forgetting Sarah Marshall is a prime example of a romantic comedy that successfully melds laughter with the complexities of relationships. Its thoughtful exploration of heartbreak and recovery, an engaging script, and exceptional performances make it a highly recommended film for fans of the genre. For those who appreciate the humor and heart found in There's Something About Mary, Forgetting Sarah Marshall delivers an equally enjoyable experience, reminding us that laughter often accompanies the ups and downs of love.

2. The 40-Year-Old Virgin (2005)

Directed by Judd Apatow, The 40-Year-Old Virgin centers on Andy Stitzer (Steve Carell), a mild-mannered electronics store worker who, at the age of 40, has never had sexual intercourse. His life takes a comedic turn when his co-workers discover this shocking fact and decide to take it upon themselves to help him lose his virginity. As they employ increasingly ridiculous tactics ranging from awkward dating advice to bizarre escapades, Andy finds himself navigating the often hilarious and uncomfortable world of modern dating while grappling with his fears and insecurities.

Steve Carell shines in his breakout role, perfectly blending humor with his character's vulnerability. The film features a stellar ensemble cast, including Catherine Keener as Trish, the woman Andy falls for; Paul Rudd as David, one of Andy's supportive yet sarcastic co-workers; and Seth Rogen as Cal, whose outrageous notions of dating often lead to uproarious moments. The chemistry among the cast enhances the film's comedic impact, making their collective antics feel genuine and relatable.

The film was released with critical acclaim, praised for its fresh comedic approach and Carell's standout performance. Grossing over $177 million worldwide, it solidified Judd Apatow's reputation as a powerhouse in the romantic comedy genre. Critics appreciated how the film balanced raunchy humor with a heartfelt narrative, allowing viewers to connect with Andy's character on an emotional level. The witty dialogue and memorable one-liners have since entered the lexicon of iconic comedy quotes.

The 40-Year-Old Virgin is credited with redefining the romantic comedy landscape in the mid-2000s by combining raunchy humor with genuine emotional arcs. It paved the way for a new wave of comedy films that embraced character depth alongside laughs. The film's exploration of themes such as love, friendship, and self-acceptance struck a chord with audiences, making it relatable to anyone navigating romance and intimacy.

At its core, the film delves into themes of connection, fear of intimacy, and the societal pressures surrounding relationships. The humor ranges from awkward scenarios—such as Andy's attempts at dating and the uproarious advice from his friends—to touching moments of authenticity when Andy confronts his insecurities and pursues a real connection with Trish. The film's blend of slapstick moments and heartfelt interactions creates a unique tone, inviting viewers to laugh while also rooting for Andy's journey toward love and self-discovery.

The 40-Year-Old Virgin stands as a landmark film in romantic comedy history, skillfully merging laughter with poignant moments of personal growth. Its clever writing, dynamic performances, and relatable themes make it a must-watch for genre fans. If you enjoyed the blend of humor and heart in There's Something About Mary, The 40-Year-Old Virgin offers a similar comedic experience that resonates long after the credits roll, reminding us that, sometimes, vulnerability is the key to genuine connection.

3. Bad Teacher (2011)

Directed by Jake Kasdan, Bad Teacher features Cameron Diaz as Elizabeth Halsey, a self-absorbed and unapologetically flawed middle school teacher who is more focused on her personal interests than educating her students. After her fiancé dumps her for a more stable woman, Elizabeth hatches a plan to win over a wealthy substitute teacher, Scott Delacorte (Justin Timberlake), in hopes of funding her breast augmentation surgery. Her reckless antics and morally questionable behavior, including manipulation, fraud, and outright laziness, lead to a series of outrageous escapades that challenge the standard expectations of a teacher's role.

Alongside Diaz, the film boasts an impressive ensemble cast, including Jason Segel as Russell Gettis, the gym teacher with a crush on Elizabeth, and Lucy Punch as Amy Squirrel, Elizabeth's overly enthusiastic and rival teacher. The dynamic between these characters adds depth to the humor, with Punch's character as a perfect foil to Elizabeth's cynical approach to teaching. Combining strong comedic talent drives the film's irreverent tone, making for memorable performances.

Released to mixed reviews, Bad Teacher garnered attention for its bold humor and Diaz's fearless portrayal of an unconventional protagonist. Critics noted that while the film indulged in raunchy humor and clichés often associated with the genre, it also offered a fresh perspective on the teacher-student dynamic and societal expectations. Ultimately, the film resonated with audiences, grossing over $100 million worldwide, solidifying its status as a cult comedy favorite.

Bad Teacher stands out for its unapologetic examination of morality and ambition in the education system. The film challenges traditional notions of a teacher's role, highlighting that not every educator is a paragon of virtue. It raises questions about ethical behavior and the lengths individuals will go to achieve their desires, all while delivering laughs. The boldness of Elizabeth's character resonates with viewers who appreciate antiheroes in comedy, allowing for deeper discussions about personal growth.

The film delves into themes of self-interest, ambition, and the comedic fallout of a morally ambiguous protagonist. Elizabeth's antics—like her outrageous attempts to manipulate her students and colleagues—create a humorous yet unsettling reflection on professionalism and ethics in teaching. The humor oscillates between dark and outrageous, employing satire to critique educational systems and societal norms cleverly. Iconic scenes, such as her unexpected teaching methods and interactions with her students, highlight the absurdity of her actions while making audiences laugh and cringe.

Bad Teacher delivers a unique spin on the romantic comedy genre, blending humor with social commentary about ambition and ethics in the workplace. Its fearless approach to storytelling and memorable characters create an enjoyable experience for those who value irreverent comedy. For fans of films like There's Something About Mary, Bad Teacher offers a similar mix of laughter and unexpected life lessons, reminding us that sometimes, the most entertaining stories emerge from the failures and follies of their characters.

4. Meet the Fockers (2004)

Directed by Jay Roach, Meet the Fockers is the highly anticipated sequel to Meet the Parents, continuing the misadventures of Greg Focker (Ben Stiller) as he prepares to introduce his quirky parents to his fiancée Pam's (Teri Polo) stern and traditional family. In this film, Greg's eccentric parents, Bernie (Dustin Hoffman) and Roz (Barbra Streisand), arrive with their unique philosophies and unfiltered personalities, turning the Focker household into a comedic battlefield. The clash of cultures between the Fockers and the Byrnes family, led by the overbearing Jack Byrnes (Robert De Niro), leads to a series of hilarious misunderstandings and escalating tensions.

The film reunites the beloved cast from the first movie while adding new dynamics with Hoffman and Streisand, who deliver standout performances. Hoffman's portrayal of Bernie, a free-spirited former lawyer and stay-at-home dad, contrasts beautifully with De Niro's uptight CIA agent. Streisand brings charm and humor as Roz, a sex therapist who isn't afraid to push boundaries. The interplay between these characters provides a wealth of comedic moments and highlights the cultural differences between the two families.

Meet the Fockers, while receiving mixed reviews from critics, was a commercial success, grossing over $516 million worldwide, making it one of the highest-grossing comedies of all time. Audiences enjoyed the comedic escalation and the chemistry between the cast members, although some noted that it lacked the freshness of its predecessor. The film's humor and character interactions resonated with viewers, solidifying its place in the romantic comedy landscape.

This sequel is built on the foundation laid by Meet the Parents, offering greater insight into Greg's upbringing and the dynamics within the Focker family. The film's exploration of parental relationships adds humor while underscoring the challenges of merging two distinctive family cultures. The success of Meet the Fockers further entrenched the original film's legacy, leading to a continued interest in the franchise and the unique ways it approached family tensions.

The film delves into themes of acceptance, parental expectations, and the unpredictability of family dynamics. The humor is driven by the clashes that arise from contrasting parenting styles, with Greg caught in the middle tof rying to please both families. Iconic scenes, such as a chaotic dinner party and the unexpected antics of Jack Byrnes as he attempts to gather intel on the Fockers, showcase slapstick moments and witty banter that highlight the absurdity of family life. The culmination of these interactions emphasizes that, despite their differences, love and family bonds ultimately prevail.

Meet the Fockers offers a delightful continuation of the comedic saga, delivering unforgettable moments and relatable themes surrounding familial relationships. Its ability to build on the humor of the original while introducing new characters and dynamics makes it a worthy follow-up. For fans of There's Something About Mary, Meet the Fockers encapsulates the chaos and heart of family life, providing a humorous look at what it means to blend two worlds amidst laughter and love.

5. HouseSitter (1992)

Directed by Frank Oz, HouseSitter is a charming romantic comedy that follows the whimsical antics of Gwen (Goldie Hawn), a carefree woman who seizes an unexpected opportunity when she meets architect Nick (Steve Martin) at his housewarming party. After Nick inadvertently leaves her out of his life plans, Gwen impulsively moves into his beautiful yet empty home, presenting herself as his fiancée to his unsuspecting friends and family. As she weaves an elaborate web of lies to maintain her facade, Gwen brings delightful chaos to Nick's life, leading to a series of comedic and heartfelt moments.

The film boasts a stellar cast led by the charismatic Goldie Hawn and the ever-charming Steve Martin. Hawn's portrayal of Gwen perfectly blends wit and charm, showcasing her knack for physical comedy and improvisational skills. As the uptight architect torn between his orderly life and Gwen's spontaneous nature, Martin delivers a nuanced performance that highlights the film's underlying themes of love and acceptance. The vibrant supporting cast, which includes Julie Harris as Nick's mother and David Packer as his friend, further enriches the story with their engaging performances.

Upon its release, HouseSitter received mixed reviews from critics, with many praising the chemistry between Hawn and Martin and the film's light-hearted charm. While some described the plot as predictable, audiences enjoyed the comedic scenarios and the warmth that emerged from the characters' evolving relationships. The film ultimately performed well at the box office, providing a delightful escape for viewers seeking light-hearted entertainment.

HouseSitter stands out as a quintessential early '90s romantic comedy, capturing the era's spirit with its blend of humor and romance. The film's exploration of deception, self-discovery, and the unpredictability of love resonates with audiences who appreciate unconventional romantic setups. Its themes of identity and the exploration of what it means to connect with another person truly are timeless, allowing it to maintain relevance in the genre.

The film masterfully explores the tension between spontaneity and order, showcasing how these differing approaches to life can lead to unexpected connections. The humor is derived from Gwen's outlandish schemes to maintain her ruse, leading to hilarious misunderstandings. Iconic moments, such as Gwen navigating Nick's social circles and the increasingly absurd situations she finds herself in, highlight the film's blend of physical comedy and witty dialogue. The film culminates in a realization that true love often flourishes when one is willing to embrace the chaos of life.

HouseSitter is a delightful romantic comedy that showcases the comedic prowess of Goldie Hawn and Steve Martin while delivering a meaningful exploration of love and identity. Its humorous take on deception and the journey to finding genuine connection creates an enjoyable viewing experience. For fans of There's Something About Mary, HouseSitter provides a similar mix of humor, heart, and the unpredictable nature of relationships, making it a worthy addition to any romantic comedy watchlist.

6. You, Me and Dupree (2006)

Directed by Anthony and Joe Russo, You, Me and Dupree is a comedic exploration of friendship, marriage, and the chaos that ensues when a laid-back slacker, Dupree (Owen Wilson), moves in with his newlywed friends, Carl (Matt Dillon) and Molly (Kate Hudson). After losing his job and apartment, Dupree becomes an unexpected houseguest, disrupting the couple's idyllic life. As he tries to find his footing, his carefree nature clashes hilariously with Carl's desire for stability and control, leading to various comedic misunderstandings that test their friendship and marriage.

The film showcases a talented ensemble, with Owen Wilson delivering one of his signature laid-back performances, effortlessly blending charm with comedic timing. Matt Dillon plays the uptight and frustrated Carl, whose slow descent into mania is both relatable and laughable. Kate Hudson shines as Molly, providing a strong emotional anchor between the two men. Additionally, supporting cast members like Michael Douglas, as Dupree's wise but unconventional mentor, and Seth Rogen in a memorable cameo further enhance the film's comedic landscape.

Upon its release, You, Me and Dupree received mixed reviews from critics, with some praising the chemistry between the leads and the film's lighthearted approach to serious themes like adulthood and responsibility. While it was noted for its predictable plot, audiences appreciated the enjoyable interplay of friendship and romance, with Wilson's humor resonating well. The film performed decently at the box office, drawing in viewers looking for a light-hearted comedy.

Though not a cultural landmark, You, Me and Dupree stands out in the landscape of mid-2000s comedies as a humorous reflection on the challenges of adult life and the importance of meaningful relationships. Its exploration of how friendship can affect a marriage is a relatable theme for many audiences, making it an enjoyable film for those navigating similar life stages.

The film humorously tackles themes of personal growth, friendship, and the importance of communication in relationships. The chaos that Dupree brings into Carl and Molly's life leads to uproarious situations—such as an ill-fated attempt at a romantic dinner that ends in disaster and a series of hijinks that blur the line between hilarity and absurdity. Memorable scenes, like Dupree's well-intentioned yet misguided advice for navigating married life, provide comic relief while also highlighting the obstacles inherent in balancing friendship and commitment. The film ultimately reinforces the idea that while life may be chaotic, the bonds of friendship can offer invaluable support during tumultuous times.

You, Me and Dupree is a comedic take on the trials of friendship and marriage, featuring lovable performances that draw viewers in. Owen Wilson's charm, Matt Dillon's comedic frustration, and Kate Hudson's grounded character create a dynamic that resonates with those familiar with the struggles of adulthood. For fans of romantic comedies like There's Something About Mary, You, Me and Dupree offers a similar blend of humor and heart, reminding viewers that life is unpredictable. Still, connection and love can make the journey worthwhile.

7. Mike and Dave Need Wedding Dates (2016)

Directed by Jake Szymanski, Mike and Dave Need Wedding Dates is a riotous comedy that centers on two hard-partying brothers, Mike (Zac Efron) and Dave Stangle (Adam Devine), infamous for their wild behavior. Tasked with finding dates for their sister's wedding in Hawaii, the brothers create a humorous social media ad outlining their outrageous personas and disastrous past experiences. However, they get more than they bargained for when their chosen dates, Alice (Anna Kendrick) and Tatiana (Aubrey Plaza), turn out to be just as reckless, leading to a series of zany adventures that jeopardize the wedding.

The film boasts a star-studded cast featuring Zac Efron, Adam Devine, Anna Kendrick, and Aubrey Plaza. Efron and Devine have outstanding comedic chemistry as rowdy brothers whose reckless antics push the boundaries of family tolerance. Kendrick and Plaza deliver sharp, witty performances that add a delightful counterbalance to the boys' wildness. Including seasoned comedic talents like Stephen Root and Anna Akana as the brothers' parents adds depth and humor to the film, showcasing a broad array of comedic styles.

Upon its release, Mike and Dave Need Wedding Dates received mixed reviews from critics, who acknowledged the film's silly premise and predictable plot. However, audiences generally enjoyed its raunchy humor and the charismatic performances of its leads, with the film grossing over $77 million worldwide. Many viewers praised the energetic chemistry between the cast and the film's ability to deliver laugh-out-loud moments, making it a solid choice for fans of a good romp.

The film explores the complexities of relationships, especially during significant life events like weddings. Highlighting the impact of misadventures on relationships prompts discussions about expectations and the importance of authenticity in confronting life's challenges. While not hailed as a classic, Mike and Dave Need Wedding Dates effectively appeal to younger audiences looking for relatable and ridiculous scenarios in a wedding setting.

At its core, the film addresses themes of love, friendship, and personal growth amid chaos. The humor is derived from the outrageous situations during the trip, including miscommunications, impulsive decisions, and the wild antics of both couples. Memorable scenes, such as the infamous wedding rehearsal dinner gone awry and the hilarious attempts to impress family members, create a high-energy atmosphere filled with comedic misunderstandings. The film balances raunchy humor with genuine, heartfelt moments as both couples learn about the meaning of true companionship and its implications on one another's lives.

Mike and Dave Need Wedding Dates offers a fun, chaotic exploration of relationships amidst the comedic backdrop of wedding planning. Efron, Devine, Kendrick, and Plaza deliver memorable performances that keep the audience engaged and laughing. For those who enjoyed the irreverent humor and relationship dynamics in films like There's Something About Mary, this movie provides similar entertainment with a light-hearted look at the trials and tribulations of love and commitment amidst laugh-out-loud escapades.

8. Little Fockers (2010)

Directed by Paul Weitz, Little Fockers serves as the third installment in the "Meet the Parents" series, continuing the comedic saga of Greg Focker (Ben Stiller) and his wife, Pam (Teri Polo), as they navigate the complexities of family life with their twins, Henry (Colin Baiocchi) and Samantha (Daisy Tormé). As Greg strives to prove himself as a dependable father and husband, tensions rise when Jack Byrnes (Robert De Niro) is concerned about the future of his family, leading him to test Greg's parenting abilities. Balancing the challenges of fatherhood, a career, and the in-laws' expectations, Greg finds himself hilariously caught in a web of misunderstandings and pressure.

The film reunites the beloved cast from the previous installments, featuring Ben Stiller, Robert De Niro, Teri Polo, and Blythe Danner. Additionally, the film introduces Jessica Alba as Andi Garcia, a new character who adds a dose of allure and complexity to Greg's life. The ensemble cast brings together their comedic talents, with De Niro reprising his role as the intimidating Jack Byrnes, whose overprotective nature heightens the stakes in every scene.

Little Fockers received mixed reviews from critics, many of whom felt it did not live up to the high standards set by its predecessors. Despite this, audiences embraced the film for its humorous take on modern family dynamics, grossing over $310 million worldwide. The return of familiar characters and nostalgic comedic setups appealed to fans, though some expressed disappointment in the film's reliance on formulaic humor rather than introducing fresh comedic elements.

While it may not be as influential as the earlier films in the franchise, Little Fockers captures the essence of family life, especially the trials of parenting and the struggle to maintain relationships amid chaos. The film's exploration of parental fears and the challenges of raising children resonates with many viewers, offering a humorous lens through which to view family dynamics. Although not critically acclaimed, it remains a popular choice for fans of the series looking for light-hearted entertainment.

The film delves into themes of parenthood, trust, and the pursuit of understanding within a family. The humor primarily stems from the generational conflicts between parents and their grown children, as well as the awkward, often absurd situations that arise during family gatherings. Memorable comedic moments include Greg's attempts to impress his father-in-law while juggling his children's antics, such as a chaotic birthday party that spirals out of control. The film effectively captures the blend of slapstick comedy and heartfelt moments, reflecting the reality that family life is often as messy as it is rewarding.

Little Fockers delivers a comedic yet relatable continuation of the iconic Meet the Parents saga, showcasing the trials of modern family life. With its ensemble cast offering a mix of humor and warmth, the film resonates with audiences familiar with the ups and downs of marriage and parenting. For fans of films like There's Something About Mary, Little Fockers provides a similar blend of comedic mishaps and touching relationships, solidifying its place in the realm of romantic comedies.

9. Ace Ventura: Pet Detective (1994)

Directed by Tom Shadyac, Ace Ventura: Pet Detective stars Jim Carrey as the titular character, a flamboyant and eccentric private investigator specializing in retrieving lost pets. When the Miami Dolphins' mascot, a stolen dolphin named Snowflake, goes missing just days before the Super Bowl, Ace is called to solve the case. His over-the-top personality, quirky investigative methods, and outrageous antics create a comedic journey filled with absurd situations and laugh-out-loud moments. As Ace delves deeper into the investigation, he navigates a host of eccentric characters and ridiculous scenarios, all while showcasing his unique flair for comedy.

Jim Carrey's iconic performance is supported by an ensemble cast that includes Courteney Cox as Melissa Robinson, a former Miami Dolphins cheerleader who becomes Ace's love interest and ally. Sean Young portrays the antagonistic character, a sportscaster involved in the case. The film also features memorable supporting performances from Tone Loc as a fellow detective and Dan Marino, the legendary Dolphins quarterback, playing himself in a humorous cameo that adds authenticity to the story.

Upon release, Ace Ventura: Pet Detective was met with mixed reviews from critics, many of whom were polarized by Carrey's outrageous persona. Nevertheless, audiences embraced the film, propelling it to box office success and earning over $107 million worldwide. Carrey's physical comedy and unique brand of humor resonated, establishing him as a leading comedic actor of the 1990s. Over time, the film has gained cult status and is often remembered for its quotable lines and Carrey's unforgettable delivery.

The film is credited with cementing Jim Carrey's status as a comedic force, largely due to his ability to fully embody the outrageous character of Ace Ventura. It showcased his unique talents in physical comedy, leading to a resurgence of interest in similar high-energy comedic styles in the years that followed. The film also highlighted the growing popularity of animal-themed comedies, influencing a wave of pet-centric movies in cinema.

At its heart, Ace Ventura: Pet Detective revolves around themes of compassion for animals and the importance of individuality. Carrey's eccentric characterization of Ace is filled with zany humor, from his bizarre catchphrases to slapstick routines, such as the infamous moment when he mimics a dolphin to draw attention to his investigation. Memorable scenes, including Ace's unconventional interrogations and his dramatic reveal of the case's resolution, epitomize the film's blend of laughter and ridiculousness.

Ace Ventura: Pet Detective remains a quintessential comedy that showcases Jim Carrey's talent for physical comedy and his ability to take audiences on a wildly entertaining journey. Its unforgettable humor and endearing moments make it a beloved classic that appeals to fans of all ages. For those who enjoyed the outrageous antics and quirky charm found in films like There's Something About Mary, Ace Ventura: Pet Detective offers a similar blend of hilarious escapades and lighthearted fun, proving that sometimes, the most unconventional detectives are the ones who get the job done.

10. Duplex (2003)

Directed by Danny DeVito, Duplex is a dark comedy that centers on a young couple, Alex (Ben Stiller) and Nancy (Drew Barrymore), who buy their dream brownstone in Brooklyn, only to discover that it comes with an unexpected catch: the elderly tenant, Mrs. Connelly (Eileen Essell), who refuses to leave. What begins as an idyllic vision of homeownership quickly spirals into a hilariously chaotic nightmare as Alex and Nancy's attempts to evict her turn into a series of absurd and increasingly desperate measures. Their frustration with Mrs. Connelly's antics escalates, leading them down a dark, comical path where they must grapple with the ethical dilemmas of their intentions.

The film features a talented cast, with Ben Stiller's charismatic comedic timing and Drew Barrymore's charm shining through their performances. Eileen Essell, as Mrs. Connelly, steals the show, perfectly embodying the quirky and unyielding nature of her character, whose antics elicit both sympathy and irritation. The ensemble also includes memorable appearances from writers like Daryl Hannah and Danny DeVito himself, whose directorial touch lends a unique blend of humor and heart to the film.

Upon its release, Duplex received mixed reviews from critics, who noted the film's uneven tone and the dark humor that permeates the storyline. While many critics agreed that the premise had promise, some felt the execution did not fully deliver. However, the chemistry between Stiller and Barrymore and the film's comedic moments resonated with audiences, allowing it to find an appreciative fan base and achieve moderate box office success.

Despite the mixed critical reception, Duplex has become a film that sparks discussions about the lengths people will go to for homeownership and the concept of gentrification. The film's exploration of morality versus personal desire reflects broader societal themes, making it relevant for audiences navigating modern real estate challenges. With its focus on the marital dynamics and the strain of unexpected situations, it offers insight into the challenges couples often face when pursuing their dreams.

At its core, Duplex examines themes of desperation, the consequences of selfishness, and the moral dilemmas associated with gentrification. The humorous scenarios that arise as Alex and Nancy try increasingly outrageous tactics to rid themselves of Mrs. Connelly—including attempting to scare her off with questionable schemes—serve to highlight the absurdity of their situation. Iconic scenes, like the couple's exaggerated attempts to make their home a peaceful haven, underscore the film's blend of slapstick humor and darker comedic undertones, all while showcasing the comedic talents of the leads as they navigate their new lives as homeowners.

Duplex presents a humorous and darkly comedic exploration of the complications that arise from the pursuit of homeownership in an ever-complicated world. With engaging performances by Ben Stiller, Drew Barrymore, and Eileen Essell, the film manages to provide both laughs and reflections on the ethical considerations of personal desires. For fans of films like There's Something About Mary, Duplex delivers a unique combination of comedy, chaos, and compelling character dynamics that make it an enjoyable watch for those who appreciate a good mix of humor and moral quandaries.

11. Pretty Woman (1990)

Directed by Garry Marshall, Pretty Woman is a classic romantic comedy that follows the unlikely love story between Vivian Ward (Julia Roberts), a spirited Hollywood sex worker, and Edward Lewis (Richard Gere), a wealthy corporate raider. When Edward needs a companion for a series of business and social events, he hires Vivian, who initially dazzles him with her free-spirited personality and confidence. As the week unfolds, their transactional arrangement evolves into a deeper connection, challenging both characters to confront their preconceived notions about love, class, and happiness.

Julia Roberts delivered a career-defining performance as Vivian, earning her a nomination for the Academy Award for Best Actress. Her charm and relatable vulnerability helped to humanize her character and draw viewers into the emotional core of the film. Richard Gere's portrayal of the suave but emotionally guarded Edward complements Roberts perfectly, showcasing their chemistry throughout the film. The cast also includes memorable performances by Hector Elizondo as the wise hotel manager, Barney Thompson, and Laura San Giacomo as Vivian's best friend, Kit, who adds depth to Vivian's backstory.

Upon its release, Pretty Woman became a box office phenomenon, grossing over $463 million worldwide and solidifying its place as one of the highest-grossing romantic comedies of all time. Critics generally praised the film for its engaging performances and charming script, and it has since become a cultural touchstone, recognized for its iconic moments and memorable lines. The film launched Julia Roberts to stardom and revitalized the romantic comedy genre in the early '90s.

Pretty Woman transformed how romantic comedies depicted relationships, especially those involving characters from different social backgrounds. The film's portrayal of the "Cinderella" narrative, where love transcends class boundaries, remains resonant today. Its success paved the way for more romantic comedies in the following decade, influencing countless films that center around finding love in unexpected places.

The film explores themes of love, self-worth, and societal judgments, challenging the stigma associated with sex work and offering a nuanced portrayal of its characters. The humor emerges from Vivian's quirky personality and her authentic reactions to the upscale world of Edward, resulting in hilarious moments, such as her attempts to fit in during high-society events. Iconic scenes, like the shopping montage in which Vivian learns about fashion, highlight not only the comedic elements but also her transformation throughout the film. The culmination of their relationship, marked by Edward's famous line, "I want the fairy tale," encapsulates the dreamy essence of love that Pretty Woman embodies.

Pretty Woman remains a beloved romantic comedy that captures the essence of love and transformation against friendship and class disparity. With standout performances from Julia Roberts and Richard Gere, the film weaves humor with heartfelt moments, making it resonate across generations. For fans of films like There's Something About Mary, Pretty Woman offers a similar blend of romantic escapades and comedic charm, reminding viewers that love can blossom in the most unlikely circumstances.

12. American Pie (1999)

Directed by Paul and Chris Weitz, American Pie is a landmark teen comedy that follows a group of high school friends—Jim (Jason Biggs), Kevin (Thomas Ian Nicholas), Oz (Chris Klein), and Finch (Eddie Kaye Thomas)—as they make a pact to lose their virginity before graduating. The film is both a humorous exploration of teenage sexuality and a heartfelt coming-of-age story, capturing adolescence's struggles, awkwardness, and hilarity. As the boys navigate their quests to fulfill the pact, they encounter various misadventures, including mishaps involving private webcasts, misguided attempts at romance, and the often tumultuous dynamics of high school relationships.

The film features a talented ensemble cast, including Alyson Hannigan as the quirky band geek Michelle, who provides one of the film's most memorable moments with her unexpected "This one time, at band camp..." line. Tara Reid portrays the popular and somewhat unattainable Vicky, who becomes the object of Kevin's affection. Seann William Scott shines as Stifler, the obnoxious yet lovable friend whose outrageous behavior often steers the group into chaos. The chemistry among the cast is palpable, contributing to the film's enduring popularity and relatable nature.

Upon its release, American Pie achieved significant commercial success, grossing over $235 million worldwide on a modest budget. Critics and audiences alike praised its candid approach to themes of teenage sexuality and relationships. While some reviews noted its crude humor, many found it refreshingly honest and relatable, capturing the awkwardness of being a teenager. The film received a strong box office reception and solidified its status as a cult classic, leading to multiple sequels and spin-offs.

American Pie is widely regarded as a watershed moment for teen comedies in the late 1990s, revitalizing the genre by addressing adolescent issues with humor and sincerity. Its open dialogue about teenage sexual exploration and the importance of authentic relationships resonated with audiences, leading to a cultural movement that paved the way for subsequent films tackling similar themes. The film's legacy includes popularizing the "coming of age" narrative during a period when such topics were often shrouded in stigma.

The film delves into themes of friendship, love, and the pressure to conform to societal expectations regarding sexuality. The humor is derived from the characters' awkward experiences and blunders, such as Jim's infamous encounter with a pie, which has become iconic in pop culture. Notable scenes include the memorable prom night escapades and the exploration of the characters' evolving relationships, showing both the hilarity and challenges of growing up. The film expertly balances raunchy humor with heartfelt moments, making it a quintessential coming-of-age story.

American Pie remains a beloved classic that captures the trials and triumphs of teenage life through its humorous and relatable lens. With standout performances, iconic lines, and a mix of laughter and heart, the film has secured its place in the pantheon of teen comedies. For fans of films like There's Something About Mary, American Pie offers a similar combination of outrageous humor and genuine exploration of love and friendship, reminding viewers that growing up is often filled with unexpected and comedic twists.

13. The Other Woman (2014)

Directed by Nick Cassavetes, The Other Woman is a romantic comedy that uniquely intertwines humor with themes of friendship and revenge. The film follows Carly Whitten (Cameron Diaz), a successful New York lawyer who discovers that her boyfriend Mark (Nikolaj Coster-Waldau) is married to another woman, Kate (Leslie Mann). Upon meeting Kate, who is blissfully unaware of Mark's infidelity, the two women form an unexpected alliance when they realize the extent of Mark's betrayal. As they join forces with the third woman in Mark's life, who is revealed to be a much younger mistress (Kate Upton), the trio devises a plan to take him down, leading to a series of hilarious and outrageous encounters.

The film boasts star power with a talented ensemble cast. Cameron Diaz shines as the confident and assertive Carly, while Leslie Mann delivers a heartfelt performance as the vulnerable and naive Kate. Kate Upton brings her glamorous presence as the spirited Amber, complementing the dynamics of the three women. The supporting cast includes Nicki Minaj in a surprising role as Lydia, Carly's outspoken assistant, whose sharp humor adds a unique flavor to the film. The chemistry among the leads is palpable, leading to comedic and emotionally resonant moments throughout the story.

Upon its release, The Other Woman received mixed reviews from critics but was well-received by audiences, grossing over $196 million worldwide. Critics praised the cast's comedic timing and the film's ability to blend humor with moments of genuine emotion. While some felt the plot relied on conventional tropes of romantic comedies, many viewers appreciated its feminist angle and the empowering message of female solidarity in the face of betrayal.

This film stands out for its exploration of female friendships and empowerment, flipping the traditional narrative of love triangles by focusing on solidarity among women instead of rivalry. By presenting the three main characters as complex individuals who choose to support each other, The Other Woman sends a positive message about overcoming adversity and finding strength in companionship. The film has sparked conversations about infidelity, empowerment, and the importance of trust in relationships.

At its core, The Other Woman delves into themes of betrayal, revenge, and female solidarity—showing that personal growth can emerge from heartbreak. The humor is driven by the stark contrasts between the characters' personalities, particularly the clash between Carly's self-assuredness and Kate's endearing innocence. Memorable comedic sequences, such as the trio's misadventures involving awkward confrontations with Mark and unexpected bonding moments during their quest for revenge, highlight the film's lighthearted approach to serious themes. The film's blend of slapstick humor and witty dialogue enables it to maintain an engaging and entertaining pace.

The Other Woman is a refreshing romantic comedy that challenges traditional narratives surrounding love and infidelity. With its engaging performances, sharp humor, and a focus on the power of female friendship, the film leaves a lasting impression on its viewers. For fans of films like There's Something About Mary, The Other Woman offers a similar mixture of charm, laughter, and the celebration of unexpected alliances, showcasing that sometimes strength comes from the most unlikely places.

14. The Other Woman (2014)

Directed by Nancy Meyers, The Holiday is a heartwarming romantic comedy that revolves around the transformative power of love and the unexpected connections that can blossom in the most unlikely circumstances. The film follows two women, Iris (Kate Winslet), a British journalist heartbroken over her unrequited love for her ex-boyfriend, and Amanda (Cameron Diaz), a successful American businesswoman who her partner has just jilted. Seeking an escape from their troubles, the two women decide to swap homes for the holidays—Iris moves into Amanda's luxurious Los Angeles mansion while Amanda heads to Iris's quaint cottage in the English countryside. As they settle into each other's lives, they encounter new possibilities for love and happiness.

Featuring a stellar cast, The Holiday showcases Kate Winslet and Cameron Diaz in lead roles, delivering emotional performances highlighting their characters' vulnerabilities and desires. The film also stars Jude Law as Graham, Iris's charming brother who unwittingly becomes a romantic interest for Amanda, and Jack Black as Miles, a film composer and friend of Iris who brings a refreshing authenticity to her life. The chemistry among the cast enhances the film's emotional depth, making their journeys relatable and engaging.

Upon release, The Holiday received mixed reviews from critics, who noted that while it followed typical romantic comedy tropes, it was elevated by the strong performances of its leads and the film's enchanting settings. Earning over $205 million worldwide, the film resonated with audiences looking for a feel-good movie that combined romance with holiday spirit. Over the years, it has become a perennial favorite during the holiday season, appreciated for its charm and heartfelt narrative.

The Holiday stands out for its focus on female empowerment and exploring self-discovery amid romantic tribulations. By highlighting the characters' journeys toward healing and personal growth, the film offers more than just a typical romantic storyline. The idea of a holiday escape leads to profound realizations about love, life, and the importance of companionship, making it relatable for viewers from various walks of life.

The film delves into themes of heartache, friendship, and the quest for identity, wrapped in the comforting embrace of the holiday season. The humor often arises from the quirky situations as the women adapt to their new environments, with Amanda's over-the-top lifestyle contrasting hilariously with small-town English traditions. Memorable moments include the comedic mishaps as Amanda navigates life in Iris's home and the delightful interactions between Jack Black and Kate Winslet, infusing genuine warmth and laughter into the narrative. The film's blend of lighthearted comedy and poignant moments underscores the essence of love and spirit—showing that sometimes, taking a leap of faith can lead to unexpected joy.

The Holiday is a delightful romantic comedy that celebrates the beauty of love, friendship, and self-discovery. With enchanting performances from a talented cast and a charming narrative, it captures the magic of the holiday season and the unexpected paths to happiness. For fans of films like There's Something About Mary, The Holiday offers a similar warmth and humor, inviting viewers to reflect on the transformative power of relationships and the joy of opening oneself up to new experiences.

15. Friends with Benefits (2011)

Directed by Will Gluck, Friends with Benefits is a modern romantic comedy that humorously tackles the complexities of relationships in a digital age. The film stars Justin Timberlake as Dylan Harper, a savvy New York City art director, and Mila Kunis as Jamie Rellis, a headhunter who convinces Dylan to relocate from Los Angeles to New York for a job opportunity. Their immediate attraction leads to a casual arrangement—friends who enjoy a physical relationship without the emotional entanglements. However, as they navigate their evolving dynamic, they quickly realize that the line between friendship and romance is not as clear-cut as they had hoped.

The film showcases the great chemistry between Timberlake and Kunis, delivering charismatic performances that bring depth to their characters. The ensemble cast features notable supporting performances from Woody Harrelson as the openly gay sports editor and friend of Dylan, who provides comedic insights and wisecracks about love, and Patricia Clarkson as Jamie's free-spirited mother, whose candid attitude about relationships adds to the film's humor. The writing cleverly combines sharp wit with heartfelt moments, ensuring the film resonates with audiences.

Friends with Benefits received generally positive reviews from critics and audiences alike upon its release, earning praise for its clever screenplay, quirky humor, and genuine chemistry between its leads. With a box office gross of over $149 million worldwide, the film stood out among the romantic comedies of 2011 and has since developed a loyal fan base. Critics noted that the film successfully navigated common genre tropes while offering fresh perspectives on the "friends-with-benefits" concept.

Friends with Benefits adeptly explores contemporary themes of commitment, intimacy, and emotional vulnerability in the digital era. By portraying modern relationships with humor and honesty, the film prompts meaningful discussions about the challenges of maintaining emotional connections in a world where casual relationships are increasingly common. Its appeal also lies in its relatable characters, who reflect many's struggles in balancing personal desires and societal expectations.

Central to the film are themes of love, friendship, and self-discovery. The humor is derived from the relatable misadventures of the two main characters attempting to keep their arrangement casual while navigating the pitfalls of attraction. Memorable comedic scenes include their attempts to redefine the rules of their relationship, leading to laugh-out-loud moments, such as their playful yet awkward attempts to detach emotionally from one another. The film cleverly parodies common romantic comedy clichés, providing a refreshing take on the genre.

Friends with Benefits is a delightful romantic comedy that captures the intricacies of modern relationships amidst a backdrop of humor and charm. With strong performances from Justin Timberlake and Mila Kunis, the film blends wit and warmth, making it a relatable choice for viewers seeking laughs and heartfelt moments. For fans of films like There's Something About Mary, Friends with Benefits offers a similar mix of romance, comedy, and the exploration of love in an effortlessly engaging way—reminding us that sometimes, the best relationships are born from an unexpected friendship.

16. My Best Friend's Wedding (1997)

Directed by P.J. Hogan, My Best Friend's Wedding is a romantic comedy that redefines the genre through its exploration of love, friendship, and the complexities of adult relationships. The film follows Julia Roberts as Julianne Potter, a successful food critic who realizes on the eve of her best friend Michael's (Dermot Mulroney) wedding that she is in love with him. Faced with the impending marriage of Michael and his charming fiancée, Kim (Cameron Diaz), Julianne embarks on a mission to win him back before it's too late. As her plans unfold, the film takes a humorous yet poignant look at the consequences of her selfish pursuits.

The film features an impressive cast, including Julia Roberts, Dermot Mulroney, Cameron Diaz, and Rupert Everett, who delivers a standout performance as George, Julianne's witty and supportive friend. Roberts' charismatic and vulnerable portrayal of Julianne captures the character's internal conflict, making her both relatable and flawed. The chemistry among the ensemble brings dynamism to the story, with Everett's comedic timing and poignant delivery providing a perfectly balanced counterpoint to Roberts' emotional turmoil.

Upon its release, My Best Friend's Wedding received positive reviews from critics, who praised its fresh take on romantic comedy tropes and the cast's solid performances. The film was a box-office success, grossing over $299 million worldwide. Critics noted that while featuring familiar rom-com elements, the film distinguished itself by exploring unrequited love and moral ambiguity.

This film has become a quintessential romantic comedy for its portrayal of the complexities of relationships and the notion that love doesn't always lead to a happy ending. It challenged traditional romantic comedy norms by focusing on a non-- classically virtuous protagonist; this shift prompted discussions on the blurred lines between friendship and love, as well as the sacrifices one is willing to make for those feelings. The film's legacy has led to a continued exploration of similar themes in modern romantic comedies.

At its core, My Best Friend's Wedding explores themes of love, self-awareness, and the intricate dynamics of friendship. Julianne's character embodies a mix of vulnerability and selfishness, leading to humorous yet often cringe-worthy situations as she attempts to intercept Michael's wedding plans. Memorable scenes include the lively karaoke performance of "I Say a Little Prayer," where George provides comic relief while highlighting the emotional stakes. The film expertly balances humor with poignant moments, ultimately underscoring that sometimes love is not enough to overcome personal shortcomings and conflicting desires.

My Best Friend's Wedding is a charming romantic comedy that showcases Julia Roberts at her best while offering a thoughtful examination of love and friendship. With its engaging storyline, a delightful supporting cast, and a mix of humor and heartache, the film resonates with audiences who appreciate deeper explorations of romantic relationships. For fans of films like There's Something About Mary, My Best Friend's Wedding provides similar layers of comedic chaos and emotional complexity, reminding viewers that love is often as complicated as beautiful.

17. Sixteen Candles (1984)

Directed by John Hughes, Sixteen Candles is a quintessential teen comedy that captures the awkwardness and excitement of adolescence. The film centers around Samantha Baker (Molly Ringwald), a high school sophomore whose sixteenth birthday is entirely forgotten by her family as they prepare for her sister's wedding. Feeling overlooked and frustrated, Samantha navigates the challenges of teenage life, including unrequited love for Jake Ryan (Michael Schoeffling), the school's heartthrob. The film humorously portrays the mishaps and miscommunications that arise as Samantha yearns for a birthday celebration and true recognition on this pivotal day.

The film features a talented ensemble cast, highlighted by Molly Ringwald's iconic performance as the relatable and sympathetic Samantha. Alongside her, Michael Schoeffling delivers a charming portrayal of Jake Ryan, whose interest in Samantha complicates the dynamics of high school relationships. The film also includes memorable performances from Anthony Michael Hall as the nerdy and lovable Farmer Ted, who provides much of the film's humor through his misguided attempts to win Samantha's affection and navigate his insecurities.

Upon its release, Sixteen Candles was met with generally positive reviews, praised for its relatable storyline and authentic depiction of teenage life. While some critics noted the film's reliance on stereotypes, audiences embraced its humor and heart, and it quickly became a cult classic. The movie's commercial success further cemented John Hughes' reputation as a leading voice in teen cinema during the 1980s.

Sixteen Candles is often credited with redefining the teen comedy genre, paving the way for subsequent films focused on the complexities of growing up. Its exploration of themes such as adolescence, identity, and the quest for acceptance resonates with viewers across generations. The film's iconic status has led to its continued relevance, inspiring countless discussions about its portrayal of teenage life and the social dynamics within high school.

The film dives into neglect, love, and the desire for acceptance, emerging as a poignant commentary on the significance of personal milestones during formative years. Humor shines through Samantha's relatable experiences, such as her awkward interactions with her family and her comedic encounters with Farmer Ted, notably highlighted in scenes where he awkwardly tries to impress her at school. The film includes several memorable moments, such as the iconic scene where Sam's cake, meant to symbolize celebration, is overshadowed by her overshadowed day. Such moments capture the essence of being a teenager, blending slapstick comedy with genuine emotion.

Sixteen Candles remains a beloved classic that encapsulates the trials and tribulations of teenage life through a humorous and heartwarming lens. The film has stood the test of time with memorable performances, engaging storytelling, and a perfect blend of comedy and sincerity. For fans of romantic comedies like There's Something About Mary, Sixteen Candles offers a similar mix of genuine emotion and laughter, reminding us of the unique and often awkward moments that shape our journey into adulthood.

18. The Heartbreak Kid (2007)

Directed by the Farrelly brothers, The Heartbreak Kid is a romantic comedy that follows the misadventures of Eddie Cantrow (Ben Stiller), a man who realizes too late that he has made the wrong choice in marrying the enthusiastic and quirky Lila (Malin Akerman) during their whirlwind courtship. As they embark on their honeymoon in Mexico, Eddie encounters the stunning and free-spirited Miranda (Michelle Monaghan), and he struggles with his inner conflict as his affection for her grows, setting off a series of humorous yet awkward situations.

In addition to Ben Stiller, Malin Akerman, and Michelle Monaghan, the film features standout performances from familiar faces like Jerry Stiller as Eddie's overbearing father and Carlos Mencia as a humorous resort manager. This ensemble adds humor and depth to Eddie's journey, showcasing the Farrelly brothers' knack for character dynamics.

Released to mixed reviews, The Heartbreak Kid garnered attention for its humorous script and the chemistry between the leads. Critics appreciated Stiller's comedic timing, stating that he brings genuine charm to Eddie's character despite the absurd predicament he finds himself in. While some reviews noted that the film leaned heavily on crude humor typical of the Farrelly style, others praised it for its moments of heartfelt reflection amidst the comedy, making it relatable to anyone who has ever grappled with love's complexities.

Though it may not have achieved the same iconic status as There's Something About Mary, The Heartbreak Kid resonates with those who've experienced the bittersweet side of romance. Its exploration of infidelity, commitment, and the ephemeral nature of attraction mirrors the struggle of many characters in romantic comedies. The film underscores the importance of self-discovery within relationships, inviting audiences to reflect on what they truly desire in love.

The film intricately weaves together themes of commitment and desire, often illustrating life's unpredictable nature. With a mix of slapstick humor, cringe-worthy situations, and tender moments, it showcases that any journey toward love and fulfillment can be fraught with unexpected detours. Fans of There's Something About Mary will find the film's blend of outrageous comedic scenarios and genuine emotion familiar and entertaining.

The Heartbreak Kid offers a funny yet insightful look into the chaos of love and relationships. It is a worthy addition to any romantic comedy list for those who appreciate films with a dose of humor and heart.

19. Sex Drive (2008)

Directed by Sean Anders, Sex Drive is a coming-of-age comedy that follows the adventurous journey of a high school senior named Ian Lafferty (Josh Zuckerman), who decides to embark on a cross-country road trip to lose his virginity to an attractive online crush named Ms. Tasty (Kaitlyn Stacey). Accompanied by his best friends, the sarcastic Felicia (Amanda Crew), and a clueless but lovable accomplice, the overweight and eccentric Glenn (Clark Duke), Ian's quest becomes a hilarious and wild romp filled with unexpected mishaps and life lessons.

The film features a talented cast, including Seth Green, who brings to life the character of Ian's overprotective older brother, along with the comedic skills of James Marsden as the charming yet reckless character, "The Biker." The ensemble effectively captures the teenage spirit, balancing genuine friendship with the universal challenges of growing up.

Sex Drive received a mixed critical response upon its release, with viewers appreciating its youthful energy and humor, especially within the teen comedy genre. Audiences praised the film for its unabashed exploration of adolescence and sexual curiosity, reminiscent of the spirit of other coming-of-age films. Despite some critiques regarding formulaic plot elements, it carved out a niche as a cult favorite among fans who enjoy raunchy yet heartfelt comedies.

While Sex Drive may not have reached the heights of legendary teen comedies, it resonates with audiences who recognize the awkwardness and excitement of navigating teenage years. The film tackles themes of self-discovery and acceptance, highlighting that the journey to maturity often comes with entertaining and awkward moments. Its unabashed focus on teenage desire provides a relatable experience for viewers reflecting on their adolescent escapades.

The film employs slapstick humor, clever one-liners, and genuine character interactions to explore themes of friendship, love, and personal growth. As Ian navigates various absurd encounters—from run-ins with quirky strangers to chaotic situations determined by his high-spirited friends—viewers are treated to laugh-out-loud moments while witnessing Ian's evolution as he learns what true intimacy and connection mean.

Sex Drive is a quintessential teen comedy that embraces the chaos of adolescent life. Its blend of outrageous situations and heartfelt moments makes it a worthwhile watch for anyone who enjoys a comedic exploration of youth and desire, offering insights beyond mere sexual pursuits. For fans of films like There's Something About Mary, Sex Drive delivers a similar mix of laughter and relatable life lessons wrapped in a fun, carefree package.

20. Meet the Parents (2000)

Directed by Jay Roach, Meet the Parents is a comedy that chronicles the comedic turmoil faced by Greg Focker (Ben Stiller) as he navigates the daunting prospect of meeting his girlfriend Pam's (Teri Polo) conservative and intimidating father, Jack Byrnes (Robert De Niro). What starts as a normal dinner quickly spirals into a series of unfortunate events, revealing Greg's many blunders as he desperately attempts to impress Jack and win his approval. This quest soon becomes hilariously complicated.

The film features an exceptional cast, including the formidable Robert De Niro, whose portrayal of Jack Byrnes adds a layer of intensity and humor to the narrative. Teri Polo delivers a charming performance as Greg's supportive girlfriend, while the film also showcases memorable roles from Blythe Danner as Pam's mother, Dina, and Owen Wilson as Pam's ex-boyfriend, Kevin, adding further comedic tension.

Meet the Parents was met with overwhelmingly positive reviews upon release, becoming one of the highest-grossing comedies ever. Critics applauded the film for its sharp script, well-timed gags, and the incredible chemistry between Stiller and De Niro, which resulted in laugh-out-loud moments and genuine tension. The film's success made it a modern classic in romantic comedy cinema.

The film has become a cultural touchstone, often referenced in discussions about the perils of meeting one's significant other's parents. Its portrayal of the awkward and often comedic dynamics of familial expectations resonates with many viewers who have experienced similar situations. Moreover, the phrase "meeting the parents" has become synonymous with the anxiety accompanying relationships, showcasing the film's influence on popular culture.

At its core, Meet the Parents explores themes of love, acceptance, and the lengths one may go to to impress family members. The humor arises from Greg's escalating mishaps, including disastrous attempts at cooking, awkward interactions, and misunderstandings—each moment exacerbating his anxiety and leading to hilarious consequences. The film masterfully balances slapstick comedy with a relatable narrative, making it a quintessential entry in the romantic comedy genre.

Meet the Parents delivers an unforgettable blend of humor and heart. Its exploration of familial relationships coupled with laugh-out-loud scenarios makes it a must-see for fans of romantic comedies. The film's timeless appeal lies in its ability to capture the universal awkwardness of love and family dynamics, providing viewers endless entertainment and life lessons. For fans of There's Something About Mary, this film offers a similar comedic essence, where love and laughter intertwine unexpectedly.

The curated films in this list share comedic elements with There's Something About Mary and delve into the complexities of love, friendship, and the humor inherent in human relationships. Each recommends a delightful mix of laughter and genuine emotion that fans of the original film will surely appreciate.

Conclusion: The curated films in this list share comedic elements with There's Something About Mary and delve into the complexities of love, friendship, and the humor inherent in human relationships. Each recommends a delightful mix of laughter and genuine emotion that fans of the original film will surely appreciate. Whether in the mood for outrageous antics or touching storytelling, these films promise an entertaining experience. For viewers eager to discover these fantastic titles, platforms like Netflix, Hulu, and Amazon Prime offer easy access for a perfect movie night.