61 of the Best RomComs of All Time

Romantic comedy is one of my absolute favorite genres. They can make you laugh, cry, and feel all warm and fuzzy inside all in one sitting. With the recent resurgence of modern romcoms (i.e. Red, White, & Royal Blue, Anyone But You, etc.) I decided to put together a list of some of the best romcoms ever made. These are in no particular order and include some of my personal favorites as well. Whether you’re in the mood for a hilarious teen comedy or want to revisit some classic love stories that never get old, this list has a pretty wide range. And if you love these movies, you should definitely check out my list of 29 feel-good movies. It’s perfect for when you need a little motivation and includes some of the same amazing films.

1. When Harry Met Sally (1989)

Directed by Rob Reiner and written by Nora Ephron, “When Harry Met Sally” stars Billy Crystal and Meg Ryan as Harry and Sally, two friends who struggle with the question of whether men and women can ever truly be just friends without romance getting in the way. This film is iconic for its witty dialogue, memorable scenes, and the exploration of male-female friendships and relationships.

2. 10 Things I Hate About You (1999)

This modern retelling of Shakespeare’s “The Taming of the Shrew” is set in a high school and directed by Gil Junger. It stars Julia Stiles as Kat Stratford and Heath Ledger as Patrick Verona. The story revolves around the attempts to set up the stubborn Kat with a date so that her more amenable sister, Bianca, can start dating.

3. The Princess Bride (1987)

Directed by Rob Reiner, “The Princess Bride” blends comedy, adventure, and romance. Starring Cary Elwes and Robin Wright, it tells the story of the beautiful Princess Buttercup and her true love, Westley, as they navigate numerous obstacles in the fantastical kingdom of Florin.

4. Crazy Rich Asians (2018)

Directed by Jon M. Chu and based on the novel by Kevin Kwan, this film stars Constance Wu as Rachel Chu, who travels to Singapore with her boyfriend, Nick Young, played by Henry Golding, only to discover that his family is one of the richest in the country. It’s a lavish romantic comedy that delves into themes of family, tradition, and the clash between old money and new values.

5. Notting Hill (1999)

Starring Julia Roberts and Hugh Grant, and directed by Roger Michell, “Notting Hill” tells the story of a British bookseller who falls in love with a famous American actress. The movie is a classic blend of British charm and Hollywood glamour, with a memorable supporting cast.

6. Bridget Jones’s Diary (2001)

Directed by Sharon Maguire and based on the novel by Helen Fielding, this film stars Renée Zellweger as Bridget Jones, a single woman who decides to take control of her life and start a diary. Colin Firth and Hugh Grant play the men vying for her affection. It’s a heartfelt comedy about love, self-improvement, and awkward moments.

7. Sleepless in Seattle (1993)

Another Nora Ephron classic, this film stars Tom Hanks and Meg Ryan. It follows a widowed father in Seattle and a Baltimore journalist who feel a connection after the former’s son calls into a radio talk show to find his father a partner. The movie is known for its cross-country romance and the chemistry between its leads.

8. My Big Fat Greek Wedding (2002)

Directed by Joel Zwick and written by its star Nia Vardalos, the film explores the cultural clashes that ensue when a Greek woman falls in love with a non-Greek man. As one of my personal favorites, I always enjoy this heartwarming story about family, identity, and love overcoming obstacles.

9. Silver Linings Playbook (2012)

Directed by David O. Russell, this film stars Bradley Cooper as a man recovering from a breakdown and Jennifer Lawrence as a young widow. Both grappling with their issues, they connect in unexpected ways. It’s a story about finding silver linings and unexpected love.

10. Love Actually (2003)

Directed by Richard Curtis, this film features an ensemble cast including Hugh Grant, Keira Knightley, and Colin Firth. It explores various aspects of love through ten interlinked stories set around Christmas in London. It’s celebrated for its heartwarming and sometimes bittersweet exploration of love in its many forms.

11. Amélie (2001)

Directed by Jean-Pierre Jeunet, “Amélie” stars Audrey Tautou as a shy waitress in Paris who decides to change the lives of those around her for the better, while struggling with her own isolation. This whimsical film is known for its unique visual style, charming narrative, and the captivating performance of its lead.

12. The Holiday (2006)

Directed by Nancy Meyers, this film stars Cameron Diaz and Kate Winslet as two women from different countries who swap homes for the holidays to escape their relationship issues, only to find love in their temporary residences. Jude Law and Jack Black play their love interests. It’s a warm, feel-good movie that celebrates new beginnings and unexpected romance.

13. 500 Days of Summer (2009)

Directed by Marc Webb, this film stars Joseph Gordon-Levitt and Zooey Deschanel in a non-linear narrative about a greeting card writer who reflects on his 500 days with a woman who doesn’t believe in true love. It’s a fresh take on romantic comedies, exploring the joys and pains of unrequited love.

14. Clueless (1995)

Directed by Amy Heckerling, this modern adaptation of Jane Austen’s “Emma” is set in a Beverly Hills high school. Starring Alicia Silverstone as Cher, a wealthy and superficial teenager who takes a new student under her wing, the film is celebrated for its sharp wit, fashion, and insightful comedy.

15. Four Weddings and a Funeral (1994)

Directed by Mike Newell and written by Richard Curtis, this British romantic comedy stars Hugh Grant and Andie MacDowell. It follows a group of friends through the titular social occasions, exploring themes of love and commitment. The film is known for its humor, charm, and the chemistry between its leads.

16. Legally Blonde (2001)

Directed by Robert Luketic, Reese Witherspoon stars as Elle Woods, a sorority girl who enrolls in Harvard Law School to win back her ex-boyfriend but discovers her potential in the process. It’s a comedy that challenges stereotypes with its empowering message and witty humor.

17. Moonstruck (1987)

Directed by Norman Jewison and starring Cher and Nicolas Cage, “Moonstruck” is a tale of a widowed, book-keeping Italian-American woman who falls in love with her fiancé’s estranged younger brother. The film is celebrated for its exploration of the complexities of love and family.

18. Crazy, Stupid, Love (2011)

Directed by Glenn Ficarra and John Requa, this film stars Steve Carell, Ryan Gosling, and Emma Stone. It follows a recently divorced man who seeks to rediscover his manhood and is taught how to pick up women at bars. The film is known for its clever script, engaging performances, and the intertwining stories of love.

19. You’ve Got Mail (1998)

Directed by Nora Ephron, this film reunites Tom Hanks and Meg Ryan as two people in an online romance unaware that they are business rivals. It’s a beloved romantic comedy for its charming leads and its exploration of love in the digital age.

20. The Proposal (2009)

Directed by Anne Fletcher, Sandra Bullock and Ryan Reynolds star in this film about a Canadian executive who learns she may face deportation from the U.S. because of her expired visa. She convinces her assistant to marry her in a sham marriage that leads to unexpected romance. It’s known for its comedic situations and the chemistry between Bullock and Reynolds.

21. La La Land (2016)

Directed by Damien Chazelle, “La La Land” stars Ryan Gosling and Emma Stone as a jazz musician and an aspiring actress, respectively, who meet and fall in love in Los Angeles. The film is a dazzling tribute to classic Hollywood musicals, filled with captivating music, dance, and a bittersweet story about dreams and love.

22. Pride & Prejudice (2005)

Directed by Joe Wright, this adaptation of Jane Austen’s novel stars Keira Knightley as Elizabeth Bennet and Matthew Macfadyen as Mr. Darcy. Set in 19th century England, it’s a story of misunderstandings, judgments, and the complexities of falling in love despite societal expectations.

23. Knocked Up (2007)

Directed by Judd Apatow, this comedy stars Seth Rogen and Katherine Heigl as a mismatched pair who have a one-night stand leading to an unexpected pregnancy. The film explores their attempt to navigate the unforeseen challenges of parenthood and relationships, with a mix of humor and genuine emotion.

24. Pretty Woman (1990)

Directed by Garry Marshall, “Pretty Woman” stars Richard Gere as a wealthy businessman and Julia Roberts as a vivacious prostitute he hires to accompany him to several social events. What starts as a business transaction evolves into a complex relationship, challenging their perceptions of love and worth.

25. The Big Sick (2017)

Directed by Michael Showalter and based on the real-life story of Kumail Nanjiani and Emily V. Gordon, “The Big Sick” stars Nanjiani and Zoe Kazan. It explores the challenges of intercultural relationships, illness, and the pressures of family expectations, all wrapped in genuine humor and emotion.

26. About Time (2013)

Directed by Richard Curtis, “About Time” stars Domhnall Gleeson as a young man who discovers he can travel in time and decides to use it to improve his love life. However, he learns that his unique gift can’t protect him and his loved ones from the problems of everyday life. It’s a touching film about love, loss, and making the most of life.

27. The Best Man (1999)

Directed by Malcolm D. Lee, “The Best Man” features an ensemble cast including Taye Diggs, Nia Long, and Morris Chestnut. The story revolves around Harper Stewart, whose forthcoming novel reveals autobiographical accounts of his college days, stirring drama when chosen as the best man for his friend’s wedding. The film skillfully blends humor with serious themes, exploring the dynamics of friendship and love.

28. 50 First Dates (2004)

Directed by Peter Segal, this film stars Adam Sandler as a veterinarian and Drew Barrymore as an amnesiac, whom he must win over repeatedly due to her short-term memory loss. Set in Hawaii, it’s a unique blend of humor and heart, exploring the lengths one will go to for love.

29. The First Wives Club (1996)

Directed by Hugh Wilson, this empowering film stars Bette Midler, Goldie Hawn, and Diane Keaton as three middle-aged women who reunite after the death of a close friend. Discovering they have all been abandoned by their husbands for younger women, they form the First Wives Club, seeking justice and personal reinvention.

30. To All the Boys I’ve Loved Before (2018)

Directed by Susan Johnson and based on the novel by Jenny Han, this film stars Lana Condor as Lara Jean, a high school junior who writes secret love letters to her crushes. When the letters are unexpectedly sent out, her love life goes from imaginary to out of control. It’s a modern teen romantic comedy that’s charming, heartfelt, and relatable.

31. Hitch (2005)

Directed by Andy Tennant, “Hitch” stars Will Smith as a professional dating consultant with a knack for helping men win over the women of their dreams. However, when he meets a journalist played by Eva Mendes, he finds his own love life challenged. This film is a witty take on love and the lengths people will go to find it.

32. 27 Dresses (2008)

Directed by Anne Fletcher, “27 Dresses” stars Katherine Heigl as a perpetual bridesmaid whose own love life is non-existent. When her younger sister gets engaged to the man she secretly loves, she starts to reevaluate her role as the perfect bridesmaid. The film explores themes of love, sacrifice, and the courage to speak your heart.

33. The Sweetest Thing (2002)

Directed by Michel Gondry and written by Charlie Kaufman, this film stars Jim Carrey and Kate Winslet as a couple who undergo a procedure to erase memories of each other after their relationship turns sour. It’s a unique and poignant exploration of love, memory, and the pain and beauty of relationships.

34. The Wedding Singer (1998)

Directed by Frank Coraci, “The Wedding Singer” stars Adam Sandler as a wedding singer from the 1980s and Drew Barrymore as a waitress with whom he falls in love. It’s a heartfelt comedy that explores themes of love and dreams amidst the vibrant backdrop of the ’80s music and fashion.

35. Two Weeks Notice (2002)

Directed by Marc Lawrence, “Two Weeks Notice” stars Sandra Bullock and Hugh Grant. Bullock plays a lawyer who, fed up with her billionaire boss’s demands (played by Grant), decides to quit her job. Their professional relationship takes a turn as they begin to see each other in a new light.

36. She’s the Man (2006)

Directed by Andy Fickman and inspired by Shakespeare’s “Twelfth Night,” “She’s the Man” stars Amanda Bynes as a high school girl who disguises herself as her twin brother to play on the boys’ soccer team, leading to comedic situations and unexpected romance with her roommate, played by Channing Tatum.

37. Something’s Gotta Give (2003)

Directed by Nancy Meyers, “Something’s Gotta Give” stars Jack Nicholson as an aging playboy who falls for the mother (played by Diane Keaton) of his young girlfriend. The film is a delightful examination of love, aging, and the unexpected ways people can connect.

38. How to Lose a Guy in 10 Days (2003)

Directed by Donald Petrie, this film stars Kate Hudson as a magazine writer who starts dating a man (played by Matthew McConaughey) to write an article on how to drive a man away in 10 days. However, her plan is complicated by the fact that he has bet that he can make any woman fall in love with him in the same time frame.

39. Bridget Jones’s Baby (2016)

Directed by Sharon Maguire, this sequel to “Bridget Jones’s Diary” sees Renée Zellweger returning as Bridget Jones. Now in her forties and single, Bridget discovers she’s pregnant but is unsure if the father is her longtime love interest, Mark Darcy (played by Colin Firth), or a new American beau, Jack (played by Patrick Dempsey).

40. Mamma Mia! (2008)

Directed by Phyllida Lloyd and based on the hit musical featuring songs by ABBA, “Mamma Mia!” stars Meryl Streep, Amanda Seyfried, and Pierce Brosnan, among others. The story revolves around a young bride-to-be who invites three of her mother’s ex-lovers to her wedding, hoping to discover which one is her father. It’s a joyous celebration of love and music on a picturesque Greek island.

41. Definitely, Maybe (2008)

Directed by Adam Brooks, “Definitely, Maybe” stars Ryan Reynolds as a father explaining his past relationships to his daughter, played by Abigail Breslin, as he goes through a divorce. The film is a charming and introspective look at love and relationships through the eyes of a single dad.

42. Just Go with It (2011)

Directed by Dennis Dugan, “Just Go with It” stars Adam Sandler as a plastic surgeon who convinces his loyal assistant, played by Jennifer Aniston, to pretend to be his soon-to-be ex-wife in order to cover up a careless lie he told his much younger girlfriend. The film is a comedy of errors that explores themes of love, friendship, and the complexities of relationships.

43. 13 Going on 30 (2004)

Directed by Gary Winick, “13 Going on 30” stars Jennifer Garner as a 13-year-old girl who makes a wish on her birthday and wakes up the next day as a 30-year-old woman. The film is a delightful exploration of adulthood, dreams, and finding true love, infused with nostalgia and humor.

44. My Best Friend’s Wedding (1997)

Directed by P.J. Hogan, “My Best Friend’s Wedding” stars Julia Roberts as a woman who realizes she’s in love with her best friend, played by Dermot Mulroney, only to find out he’s getting married. She sets out to sabotage his wedding and win him over, leading to a series of comedic and heartfelt moments.

45. Music and Lyrics (2007)

Directed by Marc Lawrence, “Music and Lyrics” stars Hugh Grant as a washed-up pop star who teams up with Drew Barrymore, a young woman with a talent for words, to write a hit song. The film is a romantic comedy that plays on the nuances of collaboration, love, and the creative process.

46. Red, White & Royal Blue (2023)

An adaptation of the bestselling novel by Casey McQuiston, this film explores the unlikely romance between Alex Claremont-Diaz, the First Son of the United States, and Prince Henry of Wales. Directed by Matthew López, it’s a modern love story that challenges societal norms, expectations, and the pressures of public life, all while delivering humor, warmth, and a heartwarming romance.

47. Love & Other Drugs (2010)

Directed by Edward Zwick and starring Jake Gyllenhaal and Anne Hathaway, “Love & Other Drugs” is set against the backdrop of the pharmaceutical sales boom of the 1990s. It follows Jamie, a charming drug rep who falls for Maggie, a young woman with Parkinson’s. Their relationship navigates through both humorous and heartfelt moments, exploring themes of love, vulnerability, and acceptance.

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

Directed by Judd Apatow and starring Steve Carell, this comedy touches on the sensitive topic of virginity with humor and heart. Carell plays Andy, a middle-aged man whose friends help him navigate the daunting world of dating. The film is celebrated for its comedic approach to adult themes and the genuine human connection at its core.

49. The Sweetest Thing (2002)

Directed by Roger Kumble, “The Sweetest Thing” stars Cameron Diaz, Christina Applegate, and Selma Blair as three friends navigating the complexities of relationships and love. The film is a raucous journey of self-discovery and female friendship, marked by its humorous take on the dating scene. Its bold humor and heartfelt moments make it a standout rom-com of the early 2000s.

50. Forgetting Sarah Marshall (2008)

Directed by Nicholas Stoller and starring Jason Segel, Kristen Bell, and Mila Kunis, this film follows Peter as he goes on a Hawaiian vacation to get over his ex-girlfriend, only to find her staying at the same hotel with her new boyfriend. It’s a comedy about heartbreak, moving on, and the unexpected paths to healing and new love.

51. She’s All That (1999)

Directed by Robert Iscove, “She’s All That” stars Freddie Prinze Jr. and Rachael Leigh Cook. It’s a classic tale of high school popularity and transformation, as a popular jock makes a bet to turn an art geek into prom queen. The film is a timeless story of love and identity, exploring the idea that true beauty comes from within.

52. Love, Rosie (2014)

Directed by Christian Ditter and based on the novel “Where Rainbows End” by Cecelia Ahern, “Love, Rosie” stars Lily Collins and Sam Claflin. It tells the story of childhood best friends whose lives take different paths but who remain connected through years of letters and missed opportunities. It’s a poignant examination of friendship, love, and fate.

53. Never Been Kissed (1999)

Directed by Raja Gosnell, “Never Been Kissed” stars Drew Barrymore as Josie Geller, a copy editor who goes undercover as a high school student for a story. Despite her initially awkward return to high school life, Josie learns invaluable lessons about love, self-acceptance, and the power of a second chance. Barrymore’s performance is both touching and hilarious, making this film a standout in the rom-com genre.

54. Sweet Home Alabama (2002)

Directed by Andy Tennant, “Sweet Home Alabama” stars Reese Witherspoon as Melanie Carmichael, a New York fashion designer who returns to her small Alabama hometown to finalize her divorce from her childhood sweetheart, Jake (played by Josh Lucas). The film charmingly explores themes of true love, identity, and the idea that you can’t escape your roots. It’s a heartwarming story that combines Southern charm with the sparkle of New York City.

55. Just Friends (2005)

Directed by Roger Kumble, “Just Friends” stars Ryan Reynolds as Chris Brander, a formerly overweight high school nerd who has transformed into a handsome and successful music executive. When Chris returns to his hometown for the holidays, he is reunited with his high school crush, Jamie Palamino, played by Amy Smart. Despite his newfound confidence, Chris finds himself reverting back to his awkward teenage self. The film hilariously explores the age-old question: Can men and women ever truly be just friends? With a mix of slapstick humor and sweet moments, “Just Friends” delivers laughs and a dose of nostalgia for unrequited high school love.

56. Bridesmaids (2011)

This Paul Feig-directed film, starring Kristen Wiig and Maya Rudolph, among others, redefined female-led comedies. Wiig plays Annie, a woman whose life unravels as she leads her best friend, Lillian (Rudolph), and a group of colorful bridesmaids on a wild ride to matrimony. “Bridesmaids” is celebrated for its brilliant blend of humor, emotion, and the exploration of friendship.

57. Fools Rush In (1997)

Directed by Andy Tennant, “Fools Rush In” stars Matthew Perry and Salma Hayek as two individuals from vastly different backgrounds who face the consequences of a one-night stand – a pregnancy. They decide to get married and navigate their cultural differences along the way. It’s a heartwarming tale of love, family, and the unexpected ways life can bring people together.

58. Picture Perfect (1997)

In this Glenn Gordon Caron film, Jennifer Aniston plays Kate, a career-oriented woman who fakes an engagement to advance her career, only to find herself entangled in a web of lies. Jay Mohr and Kevin Bacon co-star in this comedy that explores themes of love, honesty, and the pursuit of success. It’s a charming look at the lengths to which we go to achieve our dreams and find love.

59. The Truth About Cats & Dogs (1996)

Directed by Michael Lehmann, this film stars Janeane Garofalo and Uma Thurman as two women who form an unlikely friendship when Garofalo’s character, a radio show host, asks Thurman’s character to impersonate her to win a man’s affection. It’s a witty, thoughtful exploration of self-esteem, beauty standards, and love.

60. What’s Your Number? (2011)

Directed by Mark Mylod, “What’s Your Number?” stars Anna Faris as Ally Darling, a woman on a quest to find the best “ex” of her life after reading a magazine article warning that women who have had 20 or more partners have missed their chance at true love. Enlisting the help of her charming neighbor Colin, played by Chris Evans, Ally revisits her past relationships to see if she overlooked her perfect match. This romcom stands out for its humorous take on modern dating and the idea that love might just be closer than we think. Faris and Evans share amazing chemistry, making “What’s Your Number?” a heartwarming and comedic journey through the ups and downs of looking for love.

61. Brown Sugar (2002)

Directed by Rick Famuyiwa, “Brown Sugar” stars Taye Diggs as Dre, a record executive, and Sanaa Lathan as Sidney, a music critic. Both share a lifelong bond and love for hip-hop music, which plays a pivotal role in their friendship and eventual romantic journey. It’s a sweet, smart, and soulful story that delves into the music industry’s highs and lows as well as taking a friendship to the next level. “Brown Sugar” is celebrated for its heartfelt performances, memorable soundtrack, and a refreshing take on love and ambition.

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