Best Romantic Comedies of All Time, Ranked for Romantics

Cary Grant strikes again in another Howard Hawks masterpiece. This time, he's paired with Rosalind Russell in this newsroom comedy, romance, journalism flick.

A clear precedent to films like Broadcast News, His Girl Friday takes full advantage of the workplace setting as well as the “you’re marrying the wrong man” debate. It gets a little crazy towards the end, as a lot of these older Rom Coms tended to do.

A primarily female-driven story, there’s some strange housewife talk that doesn’t exactly mirror current feminists views. Still, nothing goes too far, especially considering the 1940 release date. 

The romantic comedy that starts our list earned $369 million at the box office, making it the list’s top earner. One after another men try to woo darling Mary (played by Cameron Diaz) resulting in embarrassment, devastation, and some extravagant planning.

Ben Stiller, still a relative unknown at the time, holds his weight, en route to being one of the main comedy stars of the next 10 years. It’s a pure comedy, so the dramatic beats and heavy moments are lacking, but Stiller is easy to root for, it’s a fun watch, and earns its spot.

Now, it’s unclear if the relationship in this rom com is truly romantic… but there is a kiss at the end and some definite undertones. It doesn’t help that Scarlett Johansson was 18 at the film's release while Bill Murray (always in good romantic comedies) just turned 53, but that’s neither here nor there.

The two bond over depression and pointlessness for a week in Tokyo. As opposed to the rosy, glorious display of travel, Lost In Translation flips the cliche, showing how distancing it can be. The comedy (which was largely improvised) comes from pretentious LA travelers, obsession with movie stars, and poor Japanese translation.

Combine all that with some great Bill Murray, and you get a Best Original Screenplay Oscar.

Alexander Payne follows the melancholy of About Schmidt with more despondence in Sideways. Securing his control over the depressed man genre.

Luckily, in Sideways, Payne pairs our struggling protagonist with an engaged actor friend trying to get his rocks off. Tie in some Nappy Valley waitresses, an ex-wife, and a 1961 Cheval Blanc, and you get the 05 Best Adapted Screenplay Oscar winner.

Lauded as the best wine movie of all time, the movie both catapulted sales of Pinot Noir while taking some serious slashes at the Merlot grape. If it’s any consolation to Merlot producers out there, Giamatti admits he has no wine knowledge… However, I’d guess screenwriters Alexander Payne, Jim Taylor, and source author Rex Pickett do.

Owen Wilson and Vince Vaughn, two masters of the buddy comedy, team up for this fun, at times social inappropriate comedy. The wedding is such a genre staple for the rom-com, Wedding Crashers tackles this head-on and doesn’t miss a beat.

Sure, it contains some typical plot points, but the flip allows this to still feel charming and original. It made Bradley Cooper's career, solidified Rachael Mcadams as a rom com legend, and grossed over $289 million at the box office (good for #2 on this list). It’s a classic romantic comedy in every sense.

While the plot is a little hard to get behind, if you roll with the punches, it’s a pretty layered film. The romance is central, and the comedy comes not only through dialogue and action but in editing and plot. 

Basically, a snake expert is also the heir to a fortune. He falls in love with a swindler but leaves once he finds out who she is. She then pretends to be someone else and re-enters his life. They marry, but then she lies to him about all these other men she's been with. In the end, the rich snake expert goes back to the original girl (who is actually the same girl he just married even though he doesn’t know it).

It’s a lot, especially when written out, but makes for an entertaining rom com.

For all of those that wonder what it's like to be pregnant at 17, Juno scratches the itch. It was the small little indie movie that broke out to over $230 million worldwide on a $7.5 million budget.

With a snappy Oscar-winning script (the 3rd Oscar already on this list) and a realistic take on the struggles of teen pregnancy, Juno navigates things like abortion, step-parents, high-school romance, creepy older men, and manages to be funny at the same time.

It’s not a full-blown Rom-Com, as romance is slightly lacking, but it deals a lot with different relationships, all at various stages.

Good Rom Coms

13. Funny People (2009)

The plot is in the title on this one, and in retrospect, it looks like an obvious winner. Directed by Judd Apatow and starring newcomers Steve Carell, Paul Rudd, Seth Rogan, Jonah Hill, and to some extent… Kevin Hart, it was Katheern Keener who gave the movie credibility. Crazy.

Ranking extremely high on the memorability scale, it’s the patented Apatow comedy that serves as both hilarious, and surprisingly dramatic.

The 40-Year-Old and grossed $177 million on a $26 million budget. Not bad for a directorial debut.  

Judd Apatow keeps his momentum going with his 4th installment on the best romantic comedies of all time list.

Balancing stoner life, posh Hollywood reporting, and marriage problems, Knocked Up is also full of actors just about to break out (Seth Rogan, Jonah Hill, Jason Segel, Martin Starr, Jay Baruchel, Ken Jeong).

As with all Apatow films, some of the best moments in Knocked Up are the smaller ones, spent working on fleshofthestars.com, or talking to a doorman.

It’s one of the funnier films on this list but still packs the ample drama and romance beats. I would be fine with anyone moving this higher. 

Let's be honest, I was never gonna make this list without putting Ryan Gosling on it. A force in the romance genre, Gosling shows some nice comedic chops in this pairing with Steve Carell.

Our two stars, along with a star studded-supporting cast (Kevin Bacon, Marissa Tomei, Emma Stone, Julianne Moore), weave us through intersecting storylines, love triangles, make-overs, divorces, you name it.

Very stylish, sometimes sappy, and perhaps too cool for school at times, Crazy, Stupid, Love dips its toe in a lot of dangerous water but never quite gets burned.

Probably the best Hawaii movie ever (maybe the best vacation movie ever), Forgetting Sarah Marshall takes full advantage of the resort setting with comedic bits left and right. Even the saddest moments of this film manage to be funny or lead to a great payoff.

Once again, produced by Judd Apatow. Once again, released between 2003-2009.

Another Oscar winner (Best Actress - Jennifer Lawrence), Silver Linings Playbook undoubtedly leans more into "drom" than "com."

A story about two people battling with mental instability, the comedy comes from supporting characters like Robert De Niro and Chris Tucker, who aren’t in the movie much. Is it enough to make this a rom-com? To me, the final dance sequence tips the scales.

This film is well made, well-acted, and has some tremendous moments. It was nominated for 8 academy awards and if this list was about best “movies” instead of “best romantic comedies,” it might climb even higher than #6.

Classic Romantic Comedies

5. Rushmore (1998)

An absolute classic, you can’t make a list about the best romantic comedies of all time without it. You certainly can’t make one without talking about Norah Ephron, Billy Crystal, and Meg Ryan, three Rom-Com titans (not to mention director Rob Reiner).

When Harry Met Sally... boasts incredibly witty, quick writing by Norah Ephron who shows a masterful understanding of the male mind. With only 4 major characters (2 male, 2 female), the film is extremely balanced, and we get to know our leads in and out. Most notably, the film grabbed the “Can men and women be friends?” topic before it got cliched and put a stranglehold on it.

What more can you ask for in a movie? We get sour Bill Murray (his 3rd appearance on the list) in a quirky, absurd small town. You could’ve stopped there, the comedic moments in this film are amazing, and the 2nd half love story holds up with the romantic beats of any rom-com.

Unfortunately, the Groundhog Day device (relieving the same day over and over) has itself been used over and over again in recent years. None have come close to topping the original.

Still, even if you just look at the movie itself, it’s so unique.  It feels one-of-a-kind, like a history of Woody Allen's life. It’s not made for a studio or an audience, it’s made for him.

UP NEXT

Best Romantic Movies Ever

Now that you know the best romantic comedies of all time, what’s next? Maybe you want more romance and less comedy? Up next is our ranked list of the most romantic movies ever made. From Casablanca to La La Land and everything in between, it’s time to continue our cinematic romance tour.

Up Next: Romantic movies ranked →