The 14 Best Romantic Comedies in Movie History

 Posted on July 17, 2024  |  11 minutes  |  2167 words  |  Larita Shotwell

Nothing tops falling in love, but as any fan of romantic comedies knows, there are always a few detours and roadblocks on the way to happily ever after. That’s the fun of the genre, and it’s the reason why so many of these films, from “When Harry Met Sally” to “My Best Friend’s Wedding,” remain so endlessly rewatch-able. We know the beats they need to hit, but the way they scramble and reassemble the standard plot points is what makes them really sing.

It may be true that rom-coms have fallen on hard times, consigned to streaming services like Netflix. But, with all due respect to “The Kissing Booth” and other binge-able additions to the canon, in its date night heyday, these movies provided the purest form of big-screen escapism. It’s a style of cinema that deserves to be revived in a post-pandemic world where the idea of sharing popcorn doesn’t feel quite so fraught. In honor of Valentine’s Day, here’s a look at 14 romantic comedies that will get your heart beating.

  • The American President (1995)

    Director: Rob Reiner
    Cast: Michael Douglas, Annette Bening, Martin Sheen, Michael J. Fox, and Richard Dreyfuss.
    Why You’ll Fall in Love: Given the dumpster fire that is modern American politics, it’s hard to think back to a time when many Beltway figures seemed functional, let alone admirable. So place “The American President” firmly in the fable aisle, but what a glorious fable it is. Douglas as a Clinton-esque head of state (without the personal peccadilloes) and Bening as a lobbyist (for the environment!), who fall head over heels for each other despite the political ramifications, have never been better. And Aaron Sorkin’s script is a knockout. It will make you swoon with pride in being an American again.

  • Harold and Maude (1971)

    Director: Hal Ashby
    Cast: Ruth Gordon, Bud Cort
    Why You’ll Fall in Love: This quirky May-December romance about a suicidal young man and the 79-year-old free spirit who teaches him to try something new every day may be the most life-affirming rom-com in movie history. It’s offbeat and ahead of its time, so much so that leading critics like Roger Ebert panned the movie when it debuted. But it grew into a cult classic, helped in part by Cat Stevens’ indelible soundtrack. By the final credits, you’ll be dancing along to “If You Want to Sing Out, Sing Out” and trying to follow Maude’s advice to “live life fully.”

  • Bull Durham (1988)

    Director: Ron Shelton
    Cast: Kevin Costner, Susan Sarandon, Tim Robbins
    Why You’ll Fall in Love: Costner and Sarandon explode off that screen in this comedy set in the decidedly unglamorous world of minor league baseball. It’s sensual, literate and overflowing with memorable scenes — Costner’s monologue in which he lays out the need for a Constitutional amendment outlawing astroturf and his belief that Lee Harvey Oswald acted alone, may be his greatest moment on screen. Even if you don’t know the difference between a ball and a strike, you’ll recognize that “Bull Durham” is a romantic comedy home run.

  • Crazy Rich Asians (2018)

    Director: Jon M. Chu
    Cast: Constance Wu, Henry Golding, Gemma Chan, Awkwafina, Ken Jeong, and Michelle Yeoh
    Why You’ll Fall in Love: Romantic comedies have lots of winning attributes, but as a genre there’s a shocking lack of diversity when it comes to the couples who “meet cute” on screen. “Crazy Rich Asians” provides an important corrective with its story of a Chinese American professor (Wu) who discovers her boyfriend (Golding) is a member of one of the richest families in Singapore. Better yet, the movie itself is a frothy slice of wish fulfillment that plays all the expected rom-com notes but somehow rearranges them in a way that is both modern and fresh.

  • Bridget Jones's Diary (2001)

    Director: Sharon Maguire
    Cast: Renée Zellweger, Colin Firth, Hugh Grant
    Why You’ll Fall in Love: Finally, a relatable heroine! Our Bridget smokes, drinks too much and frets about her weight. But those imperfections, along with a keen wit, also make her irresistible. Bonus points for a love triangle with palpable sizzle. Grant is all rakish sophistication as the so-wrong-he’s-right Daniel Cleaver, and Firth is priggish and principled as the much more sensible choice, Mark Darcy. Zellweger justly earned her Oscar nomination for effortlessly sliding into the role of an English single woman that, on paper, could have gone spectacularly off the rails.

  • The Philadelphia Story (1940)

    Director: George Cukor
    Cast: Cary Grant, Katharine Hepburn, James Stewart
    Why You’ll Fall in Love: Three Hollywood legends at the top of their game. That is all.

  • Laggies (2014)

    Director: Lynn Shelton
    Cast: Keira Knightley, Chloë Grace Moretz, Sam Rockwell
    Why You’ll Fall in Love: Criminally under-appreciated upon its release, “Laggies” deserves to be rediscovered. The story of a purposeless 28-year-old woman (Knightley) who runs away from a her bland boyfriend and starts hanging out with a teenager (Moretz) and her high school friends, is hilarious and relatable. After all, who among us hasn’t wanted to flee impending responsibility? And Knightley’s unexpected bond with Moretz’s father (Rockwell) is surprising in all the right ways. Most important, “Laggies” serves as a reminder of Shelton’s great, empathetic talent, which is made all the more poignant by her tragic death in 2020 at the age of 54.

  • The Big Sick (2017)

    Director: Michael Showalter
    Cast: Kumail Nanjiani, Zoe Kazan, Holly Hunter, Ray Romano, Adeel Akhtar
    Why You’ll Fall in Love: Loosely based on Nanjiani’s real-life relationship with his wife and co-screenwriter Emily V. Gordon, “The Big Sick” is the story of an underachieving Uber driver who is forced to grow up when his ex-girlfriend has a medically induced coma. Now, that’s not a premise that screams swoon-worthy, but “The Big Sick” defies the odds to offer up an on-screen romance that is honest and true, while also managing to be screamingly funny.

  • Something's Gotta Give (2003)

    Director: Nancy Meyers
    Cast: Diane Keaton, Jack Nicholson, Frances McDormand, Keanu Reeves
    Why You’ll Fall in Love: Meyers’ film is a soufflé of one-percent romance. The Hamptons house where Keaton’s playwright lives and works is pure real estate porn, and her kitchen island alone is enough to make you reexamine your life choices and head out in search of a husband or wife in high finance. But the movie is also a genuinely moving look at two mismatched, middle-aged people who find themselves unexpectedly drawn to each other. As Nicholson’s music mogul playboy recovers from a heart attack in Keaton’s beachside retreat, they share their vulnerabilities and acknowledge the tick tock of time passing them by, all while basking in some impressive ocean views. It’s a film for the dreamers and materialists in all of us.

  • My Best Friend's Wedding (1997)

    Director: P. J. Hogan
    Cast: Julia Roberts, Dermot Mulroney, Cameron Diaz, and Rupert Everett
    Why You’ll Fall in Love: Roberts is a queen of the rom-com genre, having become a star with “Pretty Woman” and a box office deity with the likes of “Notting Hill” and “Runaway Bride,” but it’s “My Best Friend’s Wedding” that sparkles brightest on her CV. That’s largely because of her willingness to play a character who can be so downright unlikable, a woman who realizes all-too-late that her best friend (Mulroney) is actually her dream man and then sets about systematically trying to destroy his wedding in a half-baked bid to win him over. Everett, as her gay editor, was robbed of an Oscar nomination and win. The Motion Picture Academy owes him a formal apology … stat.

  • When Harry Met Sally... (1989)

    Director: Rob Reiner
    Cast: Billy Crystal, Meg Ryan, Carrie Fisher, Bruno Kirby
    Why You’ll Fall in Love: Reiner and Nora Ephron crafted an unforgettable look at two neurotic New Yorkers (Crystal and Ryan) whose friendship blossoms after lots of twists and turns into unexpected romance. The dialogue, sharp and endlessly quotable, elevates the rather conventional story into the cinematic pantheon, as does the chemistry between the two leads. Ryan’s fake orgasm at Katz’s Deli has been parodied and referenced ad nauseam, but we defy you not to laugh at the punchline.

  • The Apartment (1960)

    Director: Billy Wilder
    Cast: Jack Lemmon, Shirley MacLaine, Fred MacMurray
    Why You’ll Fall in Love: The story of an office drone (Lemmon) looking to climb the corporate ladder by lending his Upper West Side apartment to company executives looking for a discrete pied-à-terre from which to conduct their extramarital flings, is much darker than the standard romantic comedy. After all, there aren’t many movies that would push its two central characters together by having one discover the other after she attempts suicide. But that’s what’s enabled “The Apartment” to endure for decades. It may be more than 60 years old, but it’s still just as effective today as it was when it first hit screens. “Shut up and deal,” indeed.

  • Four Weddings and a Funeral (1994)

    Director: Mike Newell
    Cast: Hugh Grant, Andie MacDowell, Kristin Scott Thomas, Simon Callow, Rowan Atkinson, John Hannah
    Why You’ll Fall in Love: Grant’s bumbling, warm-hearted and endlessly charming performance catapulted him to the A-list, and rightly so. But MacDowell as the winsome and sophisticated American woman he falls head over heels in love with, is equally effective. Their tender reunion in the rain earns its place in movie history, but there are so many unforgettable moments that it’s hard to choose a favorite. From Atkinson’s tongue-tied priest, stumbling his way through marriage vows, to Hannah’s deeply felt eulogy for his fallen partner, “Four Weddings and a Funeral” works because it moves effortlessly from humor to heartbreak, reminding us of the fragile line that exists between both when it comes to love.

  • Broadcast News (1987)

    Director: Jim Brooks
    Cast: Holly Hunter, Albert Brooks, William Hurt
    Why You’ll Fall in Love: The story of three hard-driving TV news hounds whose private and professional lives intersect somehow works as both an old-school romance and an acute dissection of journalistic ethics. Hunter, prickly, brilliant and also deeply insecure, is the smartest person in every room, and “it’s awful.” Brooks is her intellectual equal, but too nebbish and type A-plus to be a dream man, while Hurt is a blonde bombshell, whose looks have given him unearned success in a way that Hunter finds abhorrent. The battle to save the kind of rigorously reported, substantive broadcast journalism that Hunter’s character wants to preserve may have been lost, overshadowed by a new wave of bloviating cable news punditry, but the push and pull of romance and career still feels relevant and compelling. There’d never been a movie quite like “Broadcast News,” and there never will be again.

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