My Fave Five Romantic Comedy Films

Hello, friends! And happy Valentine’s Day!

Today is a day of expression. Today is a day of love. Today is a day of romance. When it comes to romantic films, they aren’t usually my cup of tea. However, if you combine romance in a movie with my favorite genre, comedy, well then I’m a little more likely to check that movie out. Over the years, there have been some pretty fantastic romantic comedies, particularly from directors like Gary Marshall, Nora Ephron, and Judd Apatow. I’ll admit that my experience with romantic comedies is pretty limited, not extending much before my lifetime, so all the entries on this list are fairly recent. However, I still believe you will find these to be some pretty solid selections. So without any more delay, here are my five favorite romantic comedy films.

5) Hitch

Of all the films on this list of romantic comedies, Hitch is the closest to being a pure romance film. It’s entertaining to watch Hitch, a man who has helped dozens of men find love and relationships, struggle to take the advice he so often hands out. The charismatic Will Smith has magnificent chemistry with Eva Mendes, who plays his love interest, as well as Kevin James, Hitch’s lovable insecure client. While Smith does much of the comedic heavy lifting, James provides a lot of laughs in classic James fashion. There is plenty of heart to be found in this film which is why I find myself continuously coming back to it.

4) She’s Out of My League

Jay Baruchel is the embodiment of awkwardness and my spirit animal. When his character, Kirk, meets Molly, a woman he perceives to be “out of his league,” he begins overthinking and gets in his own head. I feel that. As much as I like Baruchel, the supporting cast is top notch in this film as well. With actors and actresses like TJ Miller, Nate Torrence, Kyle Bornheimer, Krysten Ritter, Debra Jo Rupp, Geoff Stults, and Hayes MacArthur, there are laughs aplenty. While some of those names might stand out, their faces surely will. She’s Out of My League gives hope to those of us who might be a little socially awkward that there is someone out there for everyone.

3) When Harry Met Sally…

When Harry Met Sally… is the oldest film on this list and one of my more recent watches, having first seen it just three years ago. Immediately I understood why it is hailed as a rom-com classic. Vital to any romantic comedy is the chemistry between the two leads and Billy Crystal and Meg Ryan have this in spades. Their bantering feels natural and their improved story during the couples’ stories segments sounds too real to be improvised. What makes this film stand out among other romantic comedies is that it’s story doesn’t follow the same pattern as most similar films, which is refreshing when most films in the genre have a very predictable and similar template. And who can forget that diner scene? I’ll have what she’s having.

2) The 40-Year-Old Virgin

Judd Apatow has had several big hits, especially during the 2000s, but The 40-Year-Old Virgin stands out above the rest. Steve Carell is simply charming as the titular 40-year-old. Carell’s unique brand of humor mixed with Apatow’s signature style make a perfect pairing. Every scene is memorable. Catherine Keener is every bit as sweet and charming as an Ebay saleswoman as you’d expect. Together Carell and Keener with Apatow’s direction, give performances that are heartfelt and delightful. Like I’ve commented on about other films on this list, the supporting cast helps make the film. Actors like Paul Rudd, Romany Malco, and Seth Rogan make it so Carell and Keener don’t have to carry the film alone, making every minute enjoyable and memorable, a true mark of an instant classic.

1) Forgetting Sarah Marshall

Everyone who has been through a break up knows the heartbreak that often accompanies it. Sometimes you just have to get away to move on. Unfortunately for Peter, he decides that place was Hawaii, where he and his ex-girlfriend Sarah had talked about visiting together. Surprise surprise, he runs into Sarah in Hawaii. Jason Segel is an amazing choice to play the deadpan Peter, which I guess makes sense given the film was written by Segel. Opposite him is Kristen Bell who, in my eyes, is fantastic in everything she does. Throw in the likes of Russell Brand, Mila Kunis, Jonah Hill, and Jack McBrayer and you have a rom-com all-star cast. Forgetting Sarah Marshall is the perfect storm of cast, writing, and directing, offering the perfect mix of comedy and romance in a romantic comedy.

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My honorable mentions are Seeking a Friend for the End of the World, Yes Man, Home Again, There’s Something About Mary, and Crazy, Stupid, Love.

What are some of your favorite romantic comedy films?

Until next time, cheers!