20 Best Rom-Coms of All Time — Funniest Romantic Comedy Movies

By:
July 30, 2024 1:51PM EDT
50 First Dates movie poster
Sony Pictures Releasing

The only thing better than a comedy is a romantic comedy! See our list of the best rom-coms of all time.

Rom-coms have to accomplish several tasks to be successful  — make an audience laugh out loud but also bring them to tears. From 1990s hits such as Never Been Kissed to 2000s classics like 13 Going on 30, viewers love rewatching their favorite romantic comedy movies no matter how many times they’ve already seen them. Whether it be nostalgia or not, fans gravitate toward these films because of their complexities.

There is no formula to producing the perfect rom-com, but there is a handful of flicks that have gone down in cinematic history as some of the greatest of all time.

Scroll through our gallery to see a list of the 20 best rom-coms in no particular order!

1 of 20

’13 Going On 30′

’13 Going On 30′
Sony Pictures Releasing

Jennifer Garner’s character, Jenna, takes us through a time jump from 13 years old to 30 — and it’s one of the most innocent yet heartfelt cinematic experiences for fans to see before she eventually gets her pink dream house from Matty (Mark Ruffalo). 

July 29, 2024, 12:06PM
2 of 20

’50 First Dates’

’50 First Dates’
Sony Pictures Releasing

In one of Drew Barrymore and Adam Sandler’s iconic collaborations, viewers watch his character in 50 First Dates pursue the love of his life every single day because of her short-term memory loss. 

July 29, 2024, 12:06PM
3 of 20

‘Crazy Rich Asians’

‘Crazy Rich Asians’
Warner Bros. Pictures

Crazy Rich Asians tells the story of the perfect couple; both are smart, successful in their own rights and in love with each other, but there’s just one thing that might get in the way — his extremely wealthy family and his overbearing mother. 

July 29, 2024, 12:06PM
4 of 20

‘Enchanted’

‘Enchanted’
Walt Disney Studios Motion Pictures

With its fairytale trope and hilarious performances, Enchanted reigns as one of the most laugh-out-loud and sweetest romantic movies. 

July 29, 2024, 12:07PM
5 of 20

‘How to Lose a Guy in 10 Days’

‘How to Lose a Guy in 10 Days’
Paramount Pictures

Viewers watch two people unknowingly trick each other as part of individual bets, all the while unexpectedly falling in love with each other. 

July 29, 2024, 12:07PM
6 of 20

‘Never Been Kissed’

‘Never Been Kissed’
20th Century Fox

Drew Barrymore’s 1990s flick gushes with innocence and hilarity, as her character struggles to balance herself as an undercover reporter and falling in love with an unexpected Prince Charming. 

July 29, 2024, 12:07PM
7 of 20

‘Crazy, Stupid Love’

‘Crazy, Stupid Love’
Warner Bros. Pictures

With a star-studded cast, Crazy, Stupid Love is easily one of the GOATs of rom-coms, with iconic catchphrases and a twist that connects all the characters into a hilariously twisted story. 

July 29, 2024, 12:06PM
8 of 20

‘Sleepless in Seattle’

‘Sleepless in Seattle’
TriStar Pictures

With Tom Hanks and Meg Ryan, you know it’s going to be an incredible romance. After his character, Sam, loses his wife, a reporter falls for him despite being engaged. 

July 29, 2024, 12:07PM
9 of 20

‘The Wedding Singer’

‘The Wedding Singer’
New Line Cinema

Adam Sandler and Drew Barrymore’s performances in The Wedding Singer make it impossible not to laugh and tear up at how their characters finally find their way to each other. 

July 29, 2024, 12:08PM
10 of 20

‘When Harry Met Sally’

‘When Harry Met Sally’
Columbia Pictures

This 1989 movie introduces us to two college grads who spend a car ride arguing whether it’s possible for the opposite sex to remain friends, only to meet again in the future. 

July 29, 2024, 12:08PM
11 of 20

‘Clueless’

‘Clueless’
Paramount Pictures

Loosely based on Jane Austen’s hit novel Emma, Clueless follows popular matchmaker Cher, who unexpectedly falls in love with the one person who calls her out for being vain and misguided. 

July 29, 2024, 1:18PM
12 of 20

‘Sideways’

‘Sideways’
Fox Searchlight Pictures

A bachelor party trip goes completely awry when the groom seeks out one last fling, while his best man ends up falling in love with her friend. 

July 29, 2024, 1:21PM
13 of 20

‘Red, White & Royal Blue’

‘Red, White & Royal Blue’
Prime Video

With its two dedicated stars, Taylor Zakhar Perez and Nicholas Galitzine, Red, White & Royal Blue excels in telling the completely unexpected love story between the First Son of the United States, Alex, and Prince Henry of England — both of whom share an initial hate for each other that turns into something they never anticipated. 

July 29, 2024, 1:22PM
14 of 20

‘Silver Linings Playbook’

‘Silver Linings Playbook’
The Weinstein Company

Bradley Cooper and Jennifer Lawrence successfully lead this hilarious and heartfelt comedy that truly tugs on viewers’ heartstrings several times as their characters clash over their different personalities. 

July 29, 2024, 1:23PM
15 of 20

‘Jerry Maguire’

‘Jerry Maguire’
Sony Pictures Releasing

As one of Tom Cruise’s most well-known ’90s hits, Jerry Maguire follows a sports agent, who is initially blind to the fact that true love was right in front of him for a long time. 

July 29, 2024, 1:27PM
16 of 20

‘Groundhog Day’

‘Groundhog Day’
Columbia Pictures

Labeled as one of the GOATs of the rom-com genre, Groundhog Day hilariously takes viewers back in time — the same day, in fact — as Bill Murray’s character runs in desperate circles to try and figure out how time can go back to normal. 

July 29, 2024, 1:30PM
17 of 20

‘The Shop Around the Corner’

‘The Shop Around the Corner’
Metro-Goldwyn Mayer/Loew's Inc.

This 1940 classic follows a duo who is constantly at odds with one another, yet have no idea that they’re each other’s pen pal. 

July 29, 2024, 1:32PM
18 of 20

‘It Happened One Night’

‘It Happened One Night’
Columbia Pictures

As one of Frank Capra’s most famous rom-coms, It Happened One Night takes us on a complicated story as one reporter tries to help a wealthy heiress find her way back to her husband, only to fall for her. 

July 29, 2024, 1:36PM
19 of 20

‘Fire Island’

‘Fire Island’
Searchlight Pictures/Hulu

Praised by critics everywhere, Fire Island follows a group of best friends as they embark on a trip that was supposed to be a fun time but ends up being much more complicated. 

July 29, 2024, 1:39PM
20 of 20

‘The Big Sick’

‘The Big Sick’
Amazon Studios/Lionsgate

Based on a true story, The Big Sick brilliantly tells viewers a story of how one couple’s families’ cultural differences could threaten their love. 

July 29, 2024, 1:43PM