The 10 Best Romantic Comedy Duos Of All Time

These actors all had insane chemistry onscreen.

Last updated on Nov 15, 2023

Matthew McConaughey and Kate Hudson Featureflash Photo Agency | Shutterstock, Vlad, Roberto Vivancos | Canva

There is nothing better than a slightly sappy, hilarious, love-infused tale full of idealistic notions to make us feel a little lighter. Romantic comedies are simply the best, but in order for a rom-com flick to come together, casting is key. 

We want to fall head-over-heels for the screen couple's relationship, so it's nice when their chemistry is totally radiating from the screen. Well, actually, it's rather essential. But of course, some actor pairings have captured that romantic essence better than the rest, and we're counting down those duos right here.


Take a gander and see if you agree.

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Here are the 10 best romantic comedy duos of all time:

10. Hugh Grant and Sandra Bullock (Two Weeks Notice '02)

Two of the funniest actors on the planet, Two Weeks Notice brought together the team of Bullock and Grant. We'll call it comical genius. Hugh's George Wade, a big-baby businessman perpetually calls on his Chief Counsel, Sandra's Lucy, for advice on everything in his life. He drives her crazy, and she turns in her resignation. But as any quintessential rom-com follower knows, she just can't get him out of her head anymore. The antics and spark between these two have real pop, and here's to hoping these fabulous comedians star in another comedy together soon. We'll be first in line for tickets.


9. Woody Allen and Diane Keaton (Annie Hall '77)

Allen and Keaton also worked together on Manhattan, but as Robert Ebert once said, Annie Hall is "just about everyone's favorite Woody Allen movie." We would have to agree. Keaton is spot-on as the ditzy, free-spirited Annie, whom Allen's Alvy is madly in love with, despite how completely different they are (er...she is). It's a portrait of the many nuances of love portrayed perfectly by two screen legends. Sometimes offbeat is just oh-so-good.

8. Billy Crystal and Meg Ryan (When Harry Met Sally… '89)

With When Harry Met Sally, thus was born the new age of romantic comedies. How could Meg and Billy not make the list? They lit up every frame of this flick from their maiden meeting and NYC drive to fake orgasms at the diner and one of the best rom-com scenes ever, the finale at the New Year's Eve party. By the end, we didn't really care if men and women could just be friends or not. All we cared about was that Harry and Sally got together!

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7. Gregory Peck and Audrey Hepburn (Roman Holiday '53)

Audrey starred in plenty of romantic flicks in her day, from Breakfast at Tiffany's to Sabrina and Charade, but this icon was at her best in her first major role, opposite the dapper Gregory Peck in Roman Holiday. The love between Hepburn's princess and Peck's journalist on their European adventure still makes us swoon all these years later. A dose of royalty + a dashing reporter = a classic rom-com couple.


6. Matthew McConaughey and Kate Hudson (How To Lose a Guy in 10 Days '03, Fool's Gold '08)

There's something about Matthew. He was tailor-made for a roguish leading man. But there's something about Kate too. The actress brings her exuberant personality to her cute, peppy heroines. Drop these two in the same rom-com, and we'll easily fall in love. How To Lose A Guy in 10 Days pinned these two against one another, as Kate's journalist Andie attempts to drive away Matthew's Benjamin in a mere ten days for a magazine article, while his goal is to make her fall for him in the same amount of time. It's their best film together. It's cute, fun, and hilarious, just like the stars — everything a rom-com should be.

5. Cary Grant and Katharine Hepburn (The Philadelphia Story '40, Bringing Up Baby '38)

There was something so glamorous about Hepburn and Grant. They made black and white film fun and colorful in rom-coms of yesteryear. These two were the biggest stars of their time, and when they hit the screen in some serious chick flicks, no one criticized them for not being "serious actors." That in and of itself made them an unforgettable onscreen couple.

4. Adam Sandler and Drew Barrymore (The Wedding Singer '98, 50 First Dates '04)

We just adored this too-cute-for-words pair in The Wedding Singer. Their chemistry was giggle-inducing, since Drew and Adam have just the right amount of charm for rom-com roles. When they teamed up again for 50 First Dates, we were ecstatic. However, their signature fall-in-love-with-your-unavailable/engaged-friend flick was our absolute favorite. And pretty hilarious to boot.

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3. Spencer Tracy and Katharine Hepburn (Adam's Rib '49, Pat and Mike '52)

This real-life duo may have shared a complicated history, but onscreen they were always pitch-perfect. The pair starred in nine films together, including the classic rom-com Adam's Rib. Their relationship is full of tension (affairs, estrangement, and major arguments…yikes!), but their witty banter and chemistry made for some amazing cinematic romances.

2. Tom Hanks and Meg Ryan (Joe Versus the Volcano '90, Sleepless in Seattle '93, You've Got Mail '98)

Tom and Meg have dazzling chemistry in their two best-known Sleepless in Seattle and You've Got Mail, so we'd be hard-pressed to choose a favorite. We loved the instant attraction between a Seattle architect who had lost his wife and a Baltimore reporter who fell in love with him on the radio. But then there was the hilarious and sweet story of two feuding bookstore owners who are unknowingly falling in love across the internet. And we can't forget their first screen pairing ever in the now cult-classic Joe Versus the Volcano... Yeah, we really can't choose, but we can all agree that Tom and Meg as a screen couple was the cutest darn thing ever.

1. Richard Gere and Julia Roberts (Pretty Woman '90, Runaway Bride '99)

When we think of romantic comedies, Richard Gere and Julia Roberts magically surface in our minds. They made us laugh, they made us cry, and they made us desperately wish we could live inside a rom-com. Whether it's a stripper and a businessman, or a cynical journalist and a woman with perpetually cold feet, we would watch pretty much anything Jules and Gere decide to do together. We missed a flick from them in 00's, so can we please ask for a double dose in 10's?


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Jenna Birch is a former author, journalist, & editor. She currently leads narrative & communications at a venture capital firm.