The Best Romantic Comedies of All Time

It’s a contentious subject, and one on which we have to tread lightly. But as a self-appointed expert on romantic comedies (at least those of the last 10 or 20 years), I feel ready to take it on.

Rom coms are possibly some of the most polarizing movies out there. Some people- like me- LOVE them. And I mean love. As in, I would make a rom com about me and rom coms getting together and living happily ever after. Other people (unfortunately, many of whom are my friends) are not such fans. They say that this genre is predictable, boring, not action-y enough, whatever. You know what? I’m over it. More for me.

However, no matter how anti-rom-com-oriented your tastes are, there are some movies that you just have to see. If you’re that kind of person, this post is for you. And if you’re like me, this post is just another chance for you to remember how incredible your life is because these movies exist within it.

So here are the three best romantic comedies I’ve ever seen, in order from least to most favorite.

Friends With Benefits (2011)

fwb.blog By now, viewers are tired of plain old romantic comedies. As a result the bar is being set higher and higher- and this film jumps clean over with its quirky, fresh realness. It stars the young, hot, and hilarious Mila Kunis and Justin Timberlake, and also features some old favorites like Woody Harrelson of Cheers fame. The story blatantly makes fun of romantic comedies and Hollywood in general. It pits Los Angeles against New York, a rousing and passionate battle if there ever was one. It involves my personal favorite rom com trope, the best friends-turned-lovers storyline. But these things happen in ways that are not super predictable, and that actually have a lot of heart. And it’s legitimately funny. But most importantly, the message of this movie is that the person you’re with should be, more than anything else, your best friend.

Corny ending line: “Everything that happens in the day, all I can think to myself is I can’t wait to tell Jamie about this… I want my best friend back, because I’m in love with her.”

When Harry Met Sally (1989)

whms.blogThis is not WHMS’s first appearance on this blog, nor will this be its last. Come on- Billy Crystal. Meg Ryan. The ’80s. When Harry Met Sally got into some of the great differences between males and females, at a time when this stuff was not being talked about. The idea that men and women can’t be friends, the fake orgasm, all this stuff was groundbreaking. And not only that, but nobody can deny that this film is just incredibly funny. Take Billy Crystal’s improvised accents, or the random Pictionary game (“Baby fish mouth!”) It also has some pretty clever moments, like the four-way phone call, or the many parallels between Harry and Sally that they never notice.This movie is just about men and women and love. No crazy plot devices- in fact, the craziest thing is just how little actually happens. The only thing keeping these characters from each other is themselves. But when Harry does finally realize, oh my goodness is it incredible.

Corny ending line: “I came here tonight because when you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible.”

Pretty Woman (1990)

pw.blog“This is Hollywood. What’s your dream?” Pretty Woman, set in the City of Dreams, is about people living big and dreaming big and falling hard and opening up and being gorgeous the whole entire time. It’s directed by Gary Marshall (Valentine’s Day, New Year’s Eve, The Princess Diaries) and features one of the earliest acting debuts of the lovely and inspiring Julia Roberts, along with the extremely suave, attractive, and soft-hearted Richard Gere. Wow, do they make an attractive couple. This movie is by far the least realistic of the three, but what it lacks in realism, it makes up for in charm. Despite the fact that one main character is a lonely businessman and the other a sold out hooker, somehow we love them both. And they bring out the best in each other. There’s also a motif of fairytales and dreams, which is somewhere in between heartwarming and heart-wrenching, given the situation. But it makes it that much better when Edward overcomes his fear of heights to go right up to the top of Vivian’s “tower” and bring her down to be with him forever.

Corny ending line: “So what happens after he climbs up and rescues her?” “She rescues him right back.”

They may be unrealistic, but these films still have some pretty great life lessons to teach: be with your best friend. Don’t give up on others. See the best in everyone. And when you care about someone, give it your all. Maybe these movies aren’t exactly what life looks like, but they sure as heck give us something to reach for.

So there you have it. Go off into the world and spread the joy of these pieces of timeless cinematic magic. And tell ’em Leah sent you.

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