The 20 Best Romantic Comedies of All Time

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If you’re like me, then you care about romantic comedies more than most things in your life. While some people may scoff and sit on their high horse regarding this particular movie genre, I say they’re just absolutely wrong. The romantic comedy is an art form. And sadly, one that we’ve seen decline steadily in recent years (Thank you The Big Sick for bringing back in a real way).

I love romantic comedies so much it’s ridiculous, and I’m guessing that if you’re reading this list than you feel similarly. I also stick by my opinions when it comes to rom-coms and believe this to be the definitive list of the 20 best romantic comedies of the ’90s.

20. Drive Me Crazy (1999)

The quintessential teen romantic comedy, Drive Me Crazy stars ’90s it girl Melissa Joan Hart and blue-eyed dreamboat Adrian Grenier. All that on top of the fact that Britney Spears’ “Drive Me Crazy” music video featured the movie? I’M IN, Y’ALL.

19. Picture Perfect (1997)

May the queen of the ’90s reign until the earth crumbles around her! Jennifer Aniston, Jay Mohr, and Kevin Bacon star in this flick that is tragically under-viewed. Seriously, go rent it ASAP.

18. She’s All That (1999)

Oh man. How many of us recreated the “walk down the stairs and trip” moment after seeing this movie? Rachael Leigh Cook and Freddie Prinze Jr. are perfect. Also, it’s not a true romantic comedy unless the female lead transforms by merely taking off her glasses.

17. Pretty Woman (1990)

It’s Julia Roberts’ defining role. It’s so many Halloween costumes. Pretty Woman is iconic and obviously needed to go on the list. Even if it’s not your favorite, you can’t deny how badass the shopping scene is.

16. How Stella Got Her Groove Back (1998)

Angela Bassett and Taye Diggs shine in this romantic comedy of the late ’90s. It’ll make you want to renew your passport and get yourself to an island as quickly as you can. Keep reading for more ’90s rom-coms…

15. Muriel’s Wedding (1994)

Toni Collette is perhaps one of the most chameleon-like actresses of her time. She can play anything. In this romantic comedy, she is the devastatingly awkward Muriel, whose only wish is to get married.

14. As Good As It Gets (1997)

You know when people are like, “Romantic comedies suck” and you’re like, “Oh, you probably haven’t seen the right ones then.” That’s exactly the type of situation that comes up with this film. It’s good. It’s so good. It won two Oscars for crying out loud! Helen Hunt, Jack Nicholson, and Greg Kinnear are perfect in it.

13. There’s Something About Mary (1998)

It’s impossible to not fall in love with Cameron Diaz in this movie and Ben Stiller is very charming. Also, this movie always makes me want to chop my hair into a Diaz bob.

12. Clueless (1995)

CLUELESS HOLDS UP, Y’ALL. Repeat: Clueless holds up. I recently re-watched this teen romantic comedy and it was so ahead of its time, it’s insane. Plus, Paul Rudd is forever charming and somehow doesn’t age? And Brittany Murphy was so lovable in this it breaks our hearts even more that she’s no longer with us.

11. Jerry Maguire (1996)

SHOW ME THE FEELS! That’s what sums up this very ’90s, very Tom Cruse/Renée Zellweger flick. It’s so good and just full of dang charm machines. The list keeps going…

10. While You Were Sleeping (1995)

This movie is wonderfully bizarre. Seriously, the plot is bonkers but who cares when your romantic leads are Sandra Bullock and Bill Pullman. Also, it’s the whole classic fiancée mix-up scenario that honestly just works.

9. Runaway Bride (1999)

How many times can Julia Roberts appear on this list? The answer is infinite. She once again stars with Richard Gere because if it ain’t broke, don’t fix it!

8. Chasing Amy (1997)

Kevin Smith’s romantic comedy/drama is so good and to be quite honest, probably Ben Affleck’s best role. Joey Lauren Adams shines as Alyssa, a lesbian that Affleck’s character falls for.

7. My Best Friend’s Wedding (1997)

We’ve got the all star romantic comedy cast here with Julia Roberts and Cameron Diaz. Plus, Dermot Mulroney is the babe of all babes. This is just a movie you can never get tired of watching.

6. 10 Things I Hate About You (1999)

Oh man. Where to even begin with this movie? Heath Ledger! Joseph Gordon-Levitt! Julia Stiles! Alex Mack–sorry, I mean Larisa Oleynik. A baby Gabrielle Union! This cast is stacked and you’re a robot if you don’t weep when Heath sings to Julia in the bleachers. Keep reading to find out the final 5 best romantic comedies of the ’90s!

5. The Wedding Singer (1998)

This airplane scene kills me every time. Drew Barrymore and Adam Sandler are a match made in heaven and their chemistry is flawless in this hilarious and adorable rom-com.

4. Never Been Kissed (1999)

This is probably my favorite romantic comedy. Drew Barrymore, yet again, is just so lovable. You feel like you’re watching your best friend. You’re rooting for her! And then when Michael Vartan comes down to the pitcher’s mound and kisses her as The Beach Boys’ “Don’t Worry Baby” plays – ARE YOU KIDDING ME?!

3. Sleepless In Seattle (1993)

Here’s the thing about ’90s romantic comedies: when a pairing worked…it worked. Like Tom Hanks and Meg Ryan. Nora Ephron knew what she was doing when she made this movie and it’s one of those that feels like a warm blanket being thrown over your shoulders every time you watch it.

2. You’ve Got Mail (1998)

And here they are again! In one of the best movies ever made (I’ll fight you about this), You’ve Got Mail makes you want to curl up with a good book and move to New York City in the fall. Also, Greg Kinnear and Parker Posey are wonderful in it.

1. Notting Hill (1999)

Coming in first is what I consider the best romantic comedy to have ever been made – Notting Hill. Julia is queen. She’s on this list so many times, but this movie is the one that really stands out. Hugh Grant shines, Julia shines, we all shine from the amount of tears we shed…it’s just a great movie. May romantic comedies continue to turn us into piles of mush forever and always.