Over the past quarter-century, romantic comedies have seen a noteworthy evolution, moving beyond their formulaic plots to deliver bolder, more ambitious, and clever stories that are even more emotionally engaging. From genre-defining essentials that reimagine love to recent hits that highlight changing social landscapes and more space for diversity,the best romantic comedies of the last 25 years have proven that laughter and love can indeed be the most entertaining mix.
As we celebrate the most essential, from realistic and bittersweet stories to heartfelt cultural celebrations, we look back at some movies that have helped set new standards for what the genre can be, and rank the most unforgettable rom-coms to ever hit the big screens since 2000.
10’How to Lose a Guy in 10 Days' (2003)
Directed by Donald Petrie
Centering on the relationship between journalist Andie Anderson (Kate Hudson), tasked with writing an article on how to drive a man away in just ten days, and advertising executive Benjamin Barry (Matthew McConaughey), who bets his colleagues that he can make any woman fall in love with him in just the same amount of time, theDonald Petriefilm is certainly one of the most memorable recent entries in the romantic comedy genre.
Despite its mixed reviews upon release,How to Lose a Guy in 10 Dayshas become a beloved modern classic of the rom-com genre, especially with itsreappearances on streaming platformsand rediscovery by younger audiences. Its enduring appeal is far from difficult to grasp; whether it’s the unique premise or the undeniable on-screen chemistry between dynamic duo Hudson and McConaughey (who went on to star in another film together), the feel-good Petrie movie perfectly balances humor and heart, capturing the early 2000s vibe that many seem to adore.
How to Lose A Guy In 10 Days
9’My Big Fat Greek Wedding' (2002)
Directed by Joel Zwick
One of the most commercially successful romantic comedies of all time,Joel Zwick’sMy Big Fat Greek Weddingfollows 30-year-old Greek-American Toula Portokalos (Nia Vardalos), who meets and falls for Ian Miller (John Corbett), a non-Greek high school teacher, after taking computer classes and starting work at her aunt’s travel agency. Their romance quickly blossoms, but they also face some challenges given their different backgrounds.
Written by and starring Vardalos (and drawing directly from her Greek heritage),My Big Fat Greek Wedding’s popularity has maintained its status as a beloved romantic comedy classic,essentially thanks to its universal themes of family, love and cultural identity. In addition to these relatable topics and the family dynamics, Zwick’s movie provides positive visibility for Greek-Americans and immigrant families, celebrates culture and tradition, and provides a genuinely optimistic, feel-good narrative that appeals to many around the globe.
My Big Fat Greek Wedding
8’Crazy Rich Asians' (2018)
Directed by Jon M. Chu
LikeMy Big Fat Greek Wedding,Crazy Rich Asiansalso broke the mold, albeit in a different way. The first major studio rom-com in 25 years withan all-Asian castfollows Rachel Chu (Constance Wu), a Chinese-American economics professor, who travels to Singapore with her boyfriend (Henry Golding) to meet his family.
Frequently praised for its vibrant visuals and strong performances, with an extensive cast that ranges from the two protagonists toGemma Chan, Oscar-winnerMichelle Yeoh, andAwkwafina,Crazy Rich Asianshas become a cultural milestone in Hollywood for its Asian and Asian-American representation. On top of the sharp humor and heartfelt, feel-good story, the movie also breaks stereotypes and opens doors for more diverse storytelling.
Crazy Rich Asians
7’Love Actually' (2003)
Directed by Richard Curtis
Featuring ten separate but loosely connected stories exploring different aspects of love and relationships,Richard Curtis' star-packedLove Actuallyhas become anessential holiday romantic comedy. Set in London during the weeks leading up to Christmas, it follows a diverse ensemble of characters and depicts different scenarios, ranging from a newly elected Prime Minister (Hugh Grant) and his staffer (Martine McCutcheon) to a grieving widower (Liam Neeson) helping his stepson (Thomas Brodie-Sangster) pursue young love.
Love Actuallywas received far more warmly by audiences compared to critics. However,it has undeniably become a modern holiday classic, developing a cult following despite its divisiveness. Be that as it may, the nostalgic early 2000s movie and its varied portrayal of love, emotional moments, and iconic scenes (we’re looking at you, cue card confession) continue to resonate with audiences.
Love Actually
6’Legally Blonde' (2001)
Directed by Robert Luketic
StarringReese Witherspoonin one of her most memorable roles,Robert Luketic’sLegally Blondecenters around the fashionable Elle Woods, a bubbly sorority president dumped by her boyfriend, Warner (Matthew Davis). Determined to prove she’s “serious” enough as he heads to Harvard Law, Elle studies hard, gets to Harvard herself, and proves her intelligence, work ethic, and legal acumen. Fortunately, as she learns her potential along the way, she chooses her self-worth over her ex.
Although it leans more towards a comedy than a romantic comedy,Legally Blondeis now considered one of the best rom-com entries of the last 25 years; Elle is seen as a pop culture icon and has influenced a generation to embrace femininity while achieving professional success, especially in male-dominated fields. The way the movie subverts stereotypes regarding her hyper-femininity and refuses to pit intelligence against style is part of what makes the wittyLegally Blondesuch a beloved movie.
Legally Blonde
5’Bridget Jones' Diary' (2001)
Directed by Sharon Maguire
Following a 23-year-old single woman in London, self-conscious about not just her weight and job, but also about her love life,Sharon Maguire’s movie illustrates its protagonist’s journey as she resolves to improve herself, keeping a diary and finding herself torn between two men: the charming but unreliable Daniel, her boss (Grant), and the reserved and honorable Mark Darcy (Colin Firth).
A major critical and commercial success,Bridget Jones’s Diaryhas become a pop culture touchstone and one of thebest romantic comedies of the 21st century. It’s not hard to see how the movie’s influence endures through sequels and popularity — its relatable and flawed but lovable heroine that audiences can’t help but root for, the blend of British humor and memorable performances are all part of what sets the movie apart.
Bridget Jones’s Diary
4’Crazy, Stupid, Love.' (2011)
Directed by Glenn Ficarra, John Requa
This standout modern romantic comedy delivers a flawless blend of heartfelt tone, strong ensemble cast, and witty script. The film follows Cal Weaver (Steve Carrell), whose life is upended when his wife Emily (Julianne Moore) asks for a divorce after admitting to an affair. After befriend suave womanizer Jacob (Ryan Gosling), Cal embarks on a “glow-up” journey where he gets to reinvent himself with his help. Meanwhile, Jacob falls for the intriguing Hannah (Emma Watson) with unexpected results.
Known for its major final twist,Crazy, Stupid, Loveis the kind of memorable romantic comedy guaranteed to linger in the audiences’minds. Its sharp humor and originality, in addition to the fun and relatable characters and amazing chemistry between the two central couples, makeGlennFicarraandJohnRequa’s movie a must-see.
Crazy, Stupid, Love
3'500 Days of Summer' (2009)
Directed by Mark Webb
Ever since its release,Mark Webb’s500 Days of Summerhas achieved cult classic status and is often quoted as one of the best romantic films of its time — even though it’s more of a character study than a romance itself. With a non-linear narrative,500 Days of Summertells the story of Tom Hansen (Joseph Gordon Levitt), who falls deeply for his boss' new assistant, Summer Finn (Zooey Deschannel). The movie chronicles their 500-day relationship and highlights their highs and lows.
500 Days of Summerstands out in many ways, ranging from its non-linear structure and bittersweet take on romance to its clever use of visual storytelling. To this day, it remains a beloved movie to global audiences, especially those who appreciate indie and quirky but still grounded enough films. On top of all this, Webb’s captivating movie sends out valuable messages about self-discovery and our “idealized” versions of those we love.
500 Days of Summer
2’Silver Linings Playbook' (2012)
Directed by David O. Russell
Anchored by two Oscar-worthy performances byBradley CooperandJennifer Lawrence,Silver Linings Playbookfollows Pat Solitano as he returns to live with his parents in suburban Philadelphia, determined to win back his wife, who has a restraining order against him. In the meantime, Pat meets Tiffany, a young widow with her own struggles. Pat offers to help him if he partners with her in a dance competition, and a bond forms between the two.
Met with widespread acclaim and praised for its direction and amazing chemistry between the two leads,Silver Linings Playbookis a pretty solid romantic comedy that distinguishes itself by not shying away from tackling complex themeslike bipolar disorder, grief, and family dysfunction. While its legacy is complicated by ongoingcontroversies surroundingDavid O. Russell, the movie undeniably still ranks among the best and most unique entries of the last 25 years in the rom-com genre.
1’Amélie' (2001)
Directed by Jean-Pierre Jeunet
When it comes to whimsy and magical romantic comedies, no other movie comes to mind as quickly as the FrenchAmélie,a delightfulJean-Pierre Jeunetpicture starring the lovelyAudrey Tautouas the titular character. In the film, the introverted and imaginative Amélie embarks on a mission of anonymous kindness, setting out to improve the lives of her neighbors and coworkers. In the meantime, she meets Nino (Mathieu Kassovitz), an eccentric young man, and finds the courage to pursue her own happiness and love.
Those looking into getting immersed in truly beautiful,arthouse visuals, a romanticized version of the fascinating Paris, and an enchanting musical score should be sure to check out this French gem. Over two decades,Améliehas become a modern classic and a global cultural touchstone, and its influence endures whether through musicals or pop culture references.
