The Best Romantic Comedies of All Time

Image via Columbia Pictures

Jennifer Lopez had the world in the palm of her hands when The Wedding Planner dropped in 2001. That weekend she made history by becoming the first person to land the No. 1 album (J.Lo) and No. 1 movie in the country at the same time. And she deserved it. The Wedding Planner is everything a rom-com should be. It had a charming leading lady, who had given up on love, and a handsome and charismatic leading man who swoops in to reignite the desire for love in her. While falling for a client’s fiancé is not the most ethical choice, sometimes you can’t help who you love.

Will Smith took a detour from his usual blockbuster films to play the leading man in one of the best romantic comedies in recent history. Smith plays the role of Alex Hitchens, a good looking, successful “date doctor” who helps other men who aren’t lucky in love land the woman of her dreams. His world flips upside down when a reporter named Sara Melas (Eva Mendes) is on his trail with the goal of revealing his identity. As with all good rom-coms, the pair have an electric type of chemistry and the plot veers from the usual, making this a standout love story you’ll revisit again and again. The movie also featured an interracial couple and a Latina as a leading lady, which are both not often seen in this particular film genre, and it’s quite possibly what it so desperately needs.

How to Lose a Guy in 10 Days put a spin on the usual rom-com. Instead of the girl going above and beyond to get the guy of her dreams, Andie Anderson (Kate Hudson) was doing everything in her power to get rid of a handsome guy named Ben (Matthew McCoughneyhay) as part of a magazine assignment. But as romantic comedies go, it ends up becoming the article that changes her life for the better. Before his Dallas Buyers Club Oscar win, McCoughneyhay had a stint as the perfect rom-com leading man. And he is as charming as ever in this one. There’s a reason why he appears more than once on this list.

When a big-time book editor sees her stay in the United States threatened due to her immigration status, she leans on her longtime assistant to help her stay in the country. There's a reversal of power in this movie, which sees Sandra Bullock’s character being the one having to warm up to the idea of love—a characteristic that is often left to male characters. Ryan Reynolds has since become one of the world’s biggest action stars, so movies like these might be in his rearview making The Proposal even more special. The film also features one of Betty White’s last and most memorable movie performances before she passed in 2021 just weeks before her 100th birthday. Together, the ensemble cast provided a fun, laughter filled rom-com that reminds viewers that even the coldest hearts need a little love too.

50 First Dates is about a woman named Lucy who suffers from short-term memory after a tragic accident, and every day she wakes up she forgets what happened the day before. That is  until she meets a guy who makes it his life’s mission to make her remember. The movie is filled with big laughs, hilarious characters, a lot of heart, but most importantly, the chemistry between Drew Barrymore and Adam Sandler is undeniable. The pair both play their roles so well, and that’s why this is the kind of film you watch over and over again. What’s more romantic than someone committed to making their partner fall in love with them every single day? I can’t think of a more love-filled plot than that.

Tom Hanks and Meg Ryan are the ultimate rom-com power couple. They’ve teamed up for many movies through the years, but Sleepless in Seattle is our favorite. It has all the makings of a perfect romantic comedy: a widow looking for love, a career girl who’s ready to take a chance on something big, an adorable meet-cute inspired by An Affair to Remember. Gotta love that Nora Ephron movie magic.

The Princess Bride is a rom-com for everybody: It has giants, knights, monsters, and kings to satisfy your sense of adventure, a love story to keep you engaged, and perfectly timed comedy when you need a laugh. Yes, The Princess Bride is a “kissing book,” but it’s also so much more than that, especially when you realize what Wesley went through for true love.

Speaking of romantic comedies that men like, there’s no greater title in that regard than Chasing Amy. It was made by men, for men (thanks, Kevin Smith). This wonderfully complicated movie about love and sexual identity proves that not every rom-com has a fairytale ending. But it does realistically reassure us that life goes on after friendships and relationships get messy. Side note: Why isn’t Joey Lauren Adams in more things? She’s enchanting.

Nice try, Sam and Diane, but Harry and Sally are the best “will they or won’t they?” couple of all time. When Harry Met Sally is widely considered one of the best, if not THE best, romantic comedy of all time. It follows a friendship between a man and a woman for 10 years and asks questions that still plague the dating world today: Can a man and a woman ever really be just friends? Can friends sleep together without things getting weird? Once again, we have Nora Ephron to thank for this masterpiece.

What else can we say about Pretty Woman that hasn’t already been said? It’s romantic. It’s funny. It’s charming. And even though it combines Cinderella’s fairytale with sex work, it still manages to make us smile. Visions of Richard Gere snapping a jewelry box lid at Julia Roberts’s hand will happily float in our heads for the rest of eternity. (Fun fact: That scene was unscripted.)

Ah, unrequited love. A simple but compelling premise for a romantic comedy, made even more hilarious when not one, not two, not three, but four men (plus a guitarist) are lusting after the same woman. That woman is, of course, Cameron Diaz, and There’s Something About Mary came out at the height of her rule as Queen of the Rom-Coms. You’ll laugh, you’ll cheer for love, and you’ll never zip your pants carelessly ever again.

We’ve already touched on the rom-com brilliance of Julia Roberts, but there’s another big name we were still missing: Hugh Grant. Oh, Hugh Grant. Is it the eyes? The accent? Whatever “it” is, whenever he’s involved in a romantic comedy, you know it’s going to be a hit that holds up forever and ever. In Notting Hill, he plays a divorcé who owns an independent bookstore. Come on.

Usually, we’re big believers that the book is better than the movie. But for Nick and Norah’s Infinite Playlist, we’re willing to make an exception. Michael Cera and Kat Dennings are the perfect John Hughes-esque teen couple, and it’s a crime they haven’t worked together more on other projects. We’d happily take a mix CD from Nick any day and pretend to be Norah’s date any night.

Is there anything more classically romantic than a Shakespearean love story? We think not. Except for maybe modern-day adaptations of a Shakespearean love story. 10 Things I Hate About You, based on The Taming of the Shrew, is the tops. There are so many couples to root for—Patrick and Kat, Cameron and Bianca, Michael and Mandella, Ms. Perky and whomever she wants in the moment—and we feel the love from start to finish.