The Best Romantic Comedies To Warm Up With This Winter

The Wedding Singer
Courtesy of NewLine Cinema

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Who doesn’t love a good romantic comedy? Boy meets girl. Boy falls in love. Boy loses girl. Boy pulls off a giant romantic gesture and everyone gets a happily ever after. Okay, so the formula can be a little generic, and we’re definitely hurting for more films that feel representative and diverse. But in terms of what we’re working with, there are some pretty great, binge-worthy rom-coms out there, just begging to be watched this winter on your favorite streaming services.

From classics that set the tone to beloved actor matchups (ahem, Adam Sandler-Drew Barrymore and Tom Hanks-Meg Ryan), to films that offer new or updated takes on traditional tropes, here are 20 of the best romantic comedies we think you should warm up with this winter.

  

1. Roman Holiday, 1953

CAN’T-MISS CLASSIC

Gregory Peck and Audrey Hepburn had all the chemistry in this William Wyler-directed tale of a bored princess who escapes her guardians and falls in love with an American newsman in Rome. Not only is it a classic film, but it was one of the original stories of a royal falling for a commoner … and vice versa.

  

2. The Wedding Singer, 1998

BEST CHEMISTRY

It’s hard not to fall in love with the easy chemistry between Drew Barrymore and Adam Sandler in this 1980s-set romp about a wedding singer whose fiancée unexpectedly leaves him at the altar. But it’s also got spot-on costumes, hair, music and makeup, not to mention *that* airplane song at the end that’s now played at weddings everywhere.

  

3. Sleepless in Seattle, 1993

MOST ROMANTIC

Tom Hanks and Meg Ryan earned their crowns as the romantic comedy king and queen back in the early 1990s with this Nora Ephron-directed film, which has become canon over the years. People everywhere fell in love with Hanks as a widowed father whose son wanted him to find love again, and Ryan was the girl next door that everyone couldn’t help but root for.

  

4. The Big Sick, 2017

GENRE-BENDING

Kumail Nanjiani is now known for that muscular physique and for his Eternal-place in the MCU, but back before he became a superhero he was an everyday dude in this love story. Nanjiani wrote it with his wife, Emily V. Gordon, which is a good thing since it’s based on how the pair met and fell in love in real life. When it was released, critics everywhere praised its humor and originality, all while marveling at how the pair proved there are still unturned stones in the romantic comedy genre after all.

  

5. When Harry Met Sally, 1989

ROMANTIC CANON

Even if you haven’t seen this Rob Reiner-directed movie starring Billy Crystal and Meg Ryan, we’re pretty sure you’ve seen or heard of *that* diner scene. Not only is it epic, but it’s been parodied countless times since the film’s release. Plus, the story of a platonic friendship that you just don’t want to ruin with sex is pretty relatable, which always makes this one worth a watch.

  

6. Pretty in Pink, 1986

COMING-OF-AGE

John Hughes was the master of delivering coming-of-age scripts that captured (a version of) the high school experience in the 1980s, and first-time director Howard Deutch had an all-star cast to work with here. Molly Ringwald, Andrew McCarthy and Jon Cryer were the ultimate love triangle, and to this day we can’t help but root for good old Duckie every time we watch.

  

7. To All the Boys I’ve Loved Before, 2018

MODERN TEEN

Director Susan Johnson expertly oversaw this memorable adaptation of Jenny Han’s novel of the same name, which centers on a girl whose secret love letters are exposed to everyone at her high school. But it was Lana Condor and Noah Centineo who really brought the tale to life. So much so that Netflix ordered up two sequels, To All the Boys: P.S. I Still Love You and To All the Boys: Always and Forever, making this a great standalone or binge-worthy watch.

  

8. The Princess Bride, 1987

BEST FANTASY

A giant, a swordsman out for revenge, a peasant-turned-princess and a farm boy that becomes a feared pirate? Inconceivable. This Rob Reiner-directed film had an all-star cast including Mandy Patinkin, Andre the Giant, Cary Elwes, Wallace Shawn and Robin Wright in one of her very first roles. It’s a romantic comedy, but it’s also a timeless fairy tale that invokes just the right bits of fantasy.

  

9. It Happened One Night, 1934

TROPE-SETTING

Clark Gable and Claudette Colbert starred in this Frank Capra film about a renegade reporter trailing a young heiress for a story. But when the bus leaves both of them behind at one of the stops, they’re stuck with each other. It was one of the earliest stories of opposites attract, and it also became the first film to win five major Oscars (Picture, Directing, Actor, Actress and Screenplay) in the same year.

  

10. Isn’t It Romantic, 2019

TROPE-BREAKING

Director Todd Strauss-Schulson tackled pretty much every rom-com trope possible with this anti-romance rom-com that hit theatres a few years back. Rebel Wilson was the ideal leading lady who woke up trapped in a real-life fairy tale after an accident, but strong performances by Liam Hemsworth, Adam Devine and Priyanka Chopra basically sealed the deal to make this a must-watch for cynics and romantics alike.

  

11. Breakfast at Tiffany’s, 1961

BEST BOOK ADAPTATION

Truman Capote’s 1958 short novel was inspired by his time rubbing elbows with high society. So naturally, it was only a matter of time before a feature film got underway. Audrey Hepburn (in character as Holly Golightly in her black dress and tiara) is an iconic image, but if you’re into jewelry, then that alone also makes this one worth a watch.

  

12. Jerry Maguire, 1996

MOST QUOTABLE

Are you a “Show me the money!” or a “You had me at hello” kind of Jerry Maguire fan? Wherever you stand, the Tom Cruise-starring movie from writer-director Cameron Crowe was a mega-hit back in the 1990s. Not only is it one of the most quoted romantic comedys out there, but it was also a career-changing opportunity for Cuba Gooding Jr. and Renée Zellweger.

  

13. Palm Springs, 2020

ANTI-ROMANCE

Director Max Barbakow and stars Andy Samberg and Cristin Milioti delivered one of the greatest modern rom-coms with this cynical take on the genre. It revolves around two wedding guests who are stuck in a continuous time loop, but eventually they start to put aside their skeptical feelings and fall for — you guessed it! — each other.

  

14. Hitch, 2005

DATING ADVICE

Will Smith doling out love advice but not knowing how to get his own girl was the mood audiences needed in this movie 15 years ago. Rom-com aficionados appreciated that there were not one, but two budding couples to root for, with Kevin James, Eva Mendes and Amber Valletta rounding out the cast.

  

15. My Big Fat Greek Wedding, 2002

FAMILY-CENTERED

Everyone knows that when you fall for a person, you also fall for their family. Or at least that’s the expectation, right? Well, that idea was explored in full with this Joel Zwick-directed flick, which was written by star Nia Vardalos. The whole thing revolves around a Greek woman who falls for someone who isn’t Greek and then has to go about getting her family to accept him (all while learning to accept herself).

  

15. Pretty Woman, 1990

WHEN OPPOSITES ATTRACT

There are lots of commonalities between this Garry Marshall-directed movie and Breakfast at Tiffany’s, but this is also the movie that basically launched Julia Roberts’ career. Her chemistry with Richard Gere was top-notch (and inspired their reunion in the lesser loved, 1999 film Runaway Bride), while the movie itself reminded us all that you should never judge a book by its cover.

  

16. Knocked Up, 2007

UNEXPECTED ROMANCE

Who knew that a love story between Seth Rogen and Katherine Heigl would be so … lovely? This easy watch from writer-director Judd Apatow took many by surprise when it debuted, but the premise of being “stuck” in a relationship with someone because of life circumstances (read: a baby) resonated. Of course, a stellar supporting cast led by Paul Rudd, Leslie Mann and Jason Segel didn’t hurt, which is probably why they all reprised their roles for the Rogen- and Heigl-free 2012 follow-up, This Is 40.

  

17. Wedding Crashers, 2005

BUDDY-BUDDY

Even if it’s not wedding season you can always grab your best buds, pretend you run a maple syrup conglomerate in Vermont, and settle in for a re-watch of this Vince Vaughn, Owen Wilson movie from director David Dobkin. Sure, this is the story of two guys who crash weddings to meet women, but at its core, it too is a rom-com — one that features equally funny ladies Rachel McAdams and Isla Fisher.

  

18. Shakespeare in Love, 1998

A TOUCH OF SHAKESPEARE

There are plenty of Shakespearean love stories out there, so why shouldn’t the guy get his own? Director John Madden recruited a pre-GOOP Gwyneth Paltrow and Joseph Fiennes for this fictional take on the playwright and his unexpected muse. Is it historically accurate? Not at all. But it’s undeniably romantic, and it cleaned up at the Oscars that year, taking home seven trophies, including Best Picture.

  

19. While You Were Sleeping, 1995

MOST HOPELESSLY ROMANTIC

Just one year after Sandra Bullock became a household name in Speed, she starred in this John Turteltaub-directed movie about a woman who falls in love with a man in a coma. Much like the lead character herself, this movie is hopelessly romantic and pretty darned unrealistic, but like all good romantic comedies if you suspend your disbelief you’ll probably be into its happy ending.

  

20. Groundhog Day, 1993

BEST RE-WATCH

If you’ve seen all the romantic movies out there, then this is the one you should definitely re-watch over and over again. The Bill Murray, Andie MacDowell starring movie about February’s lesser-known “holiday” basically wrecked Murray’s relationship with director Harold Ramis. But the end result totally — and hilariously — withstands the test of time. It’s also ranked one of Murray’s best all-time movies on Rotten Tomatoes, coming in right behind Ghostbusters (naturally).

  

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