The Definitive Ranking of Romantic Comedy Excellence
Filled with weddings, sardonic best friends, and an abundance of Julia Roberts, these are the greatest romantic comedies ever created, perfectly curated for viewing this Valentine's Day. Compiled and ranked by film critic Adam White from 25 to 1, this list celebrates the genre that has survived clichés, shifting cultural mores, and countless imitators.
The Criteria for Romantic Comedy Greatness
To assemble the genre's 25 finest examples, strict criteria were maintained. A true romantic comedy must build to a final emotional crescendo and conclude with a kiss, eliminating films like Working Girl. Additionally, the central romance must serve as the primary narrative hook throughout the entire film, which excludes beloved titles such as Clueless or Legally Blonde.
The usual rules of "good filmmaking" do not necessarily apply here. The best romantic comedies represent an immaculate fusion of perceptive storytelling, exceptional humour, and chemistry in abundance. Sometimes, audiences simply desire to watch attractive actors flirt in picturesque surroundings. Ultimately, we are all lovesick romantics standing before screens, asking to witness beautiful people fall in love.
The Countdown: From 25 to 1
25. Pretty Woman (1990) - Beginning with the obvious, Pretty Woman possesses a disquieting sleaziness, originally conceived as a gritty sex work drama ending tragically. Thankfully, rewrites transformed it into a Disney-fied fantasy featuring Julia Roberts in star-is-born mode. Richard Gere's character, an LA businessman who hires an escort, remains slightly maddening, yet the film miraculously renders this ickiness romantic.
24. There's Something About Mary (1998) - Emerging from the gross-out comedy boom, this film is rescued from comic oblivion by Cameron Diaz's radiant performance as the sunny dream girl pursued by variously depraved men. Her daffy, committed portrayal launched her into Hollywood stardom.
23. Gentlemen Prefer Blondes (1953) - Marilyn Monroe's rendition of "Diamonds Are a Girl's Best Friend" remains iconic, while her double act with Jane Russell exudes chic sophistication. The film boasts a surprisingly sex-positive and self-aware quality for its era, with Monroe and Russell portraying scrappy, ambitious women who could effortlessly dominate their dull love interests.
22. Get Over It (2001) - An underrated masterpiece from the US teen-movie boom, this Shakespeare-inspired parody features Ben Foster as a dumped basketball player who joins the school play to win back his ex, only to fall for Kirsten Dunst's adorable character. Martin Short steals the show as a flamboyant drama teacher.
21. Boomerang (1992) - As the first Black mainstream romantic comedy with aspirational sheen, this lively battle-of-the-sexes film stars Eddie Murphy as a womanising executive spurned by his female counterpart, Robin Givens. Supported by Grace Jones and Halle Berry, Givens delivers a sparkling performance overshadowed by her personal life.
20. Love Actually (2003) - Richard Curtis's annually inescapable Christmas behemoth features six or seven standout set pieces embedded in cultural memory. Despite criticisms of cutesiness or misogyny, it remains a classic of the form—masterfully structured, endlessly watchable, and depicting love in all its compelling colours.
19. But I'm a Cheerleader (1999) - Set in a gay conversion camp, this satirical comedy focuses on the brewing relationship between Clea DuVall and Natasha Lyonne's characters. Their mutual attraction develops under the watch of Cathy Moriarty's den mother, creating a memorable pink satin-coloured debut.
18. Groundhog Day (1993) - Often forgotten as a romantic film, this masterpiece centres on Bill Murray's obnoxious weatherman stuck in a time loop, bettering himself to win over Andie MacDowell's initially disdainful TV producer. The love story highlights how personal growth makes trials worthwhile.
17. Bull Durham (1988) - Defying genre norms, this film depicts sex openly, with Susan Sarandon as a free-spirited baseball groupie who selects one player per season. Her involvement with Kevin Costner and Tim Robbins sparks an erotically charged dynamic.
16. Say Anything... (1989) - Cameron Crowe's film explores fixation and co-dependency, with Ione Skye caught between two needy men. Despite creepy undercurrents, Skye and John Cusack's impeccable chemistry and the iconic boombox scene render it strikingly romantic.
15. Modern Romance (1981) - An anti-romcom, Albert Brooks's film delves into narcissistic neurosis as a Los Angeles film editor dissects his relationship to death. It portrays love as toxic and unbearable with gnarly wit.
14. The Wedding Singer (1998) - Adam Sandler and Drew Barrymore's shared sensibilities—sweet-natured, earnest, and goofy—create transfixing chemistry. Soundtracked by 1980s pop classics, this nostalgic film remains endlessly rewatchable.
13. Bridget Jones's Diary (2001) - Renée Zellweger's flawless portrayal of the very English Bridget Jones, with her neurotic melancholy, makes the character immensely likeable. Featuring Colin Firth and Hugh Grant, the film offers comfort through slapstick and a perfect Christmas finale.
12. Moonstruck (1987) - Cher's Oscar-winning performance as a Brooklyn widow who transforms after falling for her soon-to-be brother-in-law (Nicolas Cage) blends love story with magical whimsy. It explores abandoning a resigned life for the unknown.
11. Four Weddings and a Funeral (1994) - This sleeper hit, starring Hugh Grant and written by Richard Curtis, follows friends through four weddings and a funeral. Despite an underwritten female lead, it features a heart-wrenching gay subplot and magnanimous displays of unrequited love.
10. Roman Holiday (1953) - A perfect encapsulation of the 1950s, this classic pairs Audrey Hepburn's regal princess with an ordinary journalist, inspiring countless later films. Its timeless charm and European jet-set allure remain irresistible.
9. My Best Friend's Wedding (1997) - Julia Roberts delivers a daring performance as a single woman determined to destroy her best friend's wedding to a naive rich girl (Cameron Diaz). The film's darkness, mixed with 1990s sheen, makes it intriguing and secretly brilliant.
8. 10 Things I Hate About You (1999) - A smart, heartwarming comedy with feminist politics, featuring Heath Ledger and Julia Stiles as "unappealing" high schoolers whose romance is engineered. Their authentic, charming chemistry burns the screen.
7. Annie Hall (1977) - Despite controversies surrounding Woody Allen, this film showcases Diane Keaton at her most daffy, stylish, and cool. She transcends the idealised fantasy figure through sheer force of will.
6. The Apartment (1960) - Billy Wilder's masterpiece presents Christmas in melancholy splendour, with Jack Lemmon and Shirley MacLaine as lonely souls finding connection. MacLaine's bruised yet eager performance provides the film's heart.
5. The Philadelphia Story (1940) - A fizzy treasure setting the tone for future comedies, Katharine Hepburn plays an heiress torn between three men: her dull fiancé, a prickly journalist (James Stewart), and her ex (Cary Grant). The film exudes vintage movie-star glamour.
4. Notting Hill (1999) - The apex of British romantic comedy, this film features Hugh Grant as a bookseller falling for an A-list movie star (Julia Roberts). With immaculate swooshes of hair and Working Title charm, it is incredibly funny, gentle, and confident.
3. You've Got Mail (1998) - Tom Hanks and Meg Ryan reunite as sworn enemies in a bookshop war who fall in love anonymously online. Despite dial-up modems, the film's timeless chemistry and Ryan's brilliant performance ensure it ages beautifully.
2. What's Up, Doc? (1972) - Peter Bogdanovich's blockbuster collides slapstick, romance, and shocking sex appeal, with Barbra Streisand and Ryan O'Neal as unlikely allies. It serves as the blueprint for madcap action-romances.
1. When Harry Met Sally... (1989) - The undeniable champion, this film kickstarted the 1990s romcom boom and invented many clichés: sardonic best friends, late-night phone calls, holiday climaxes, and hilarious honesty about sex. With Billy Crystal, Meg Ryan, and Nora Ephron's script, it set a glorious benchmark for the genre.
