Top 5 Romantic Comedies

Top 5 Romantic Comedies

In celebration of the upcoming Valentine’s Day holiday, it seems only appropriate to have our Top 5 reflect the most famous of Hallmark co-opted Catholic celebrations. We’ve asked fabulous and prolific contributor, Alexis Johnson, to give us her Top 5 Romantic Comedies, which she was more than obliged to provide.

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5) TIE!

I know, I know… It’s kind of a cop-out for a top five list to have a tie, especially right out of the gate, but it couldn’t be helped. 

13 going on 30.
13 going on 30.

5a) 13 Going On 30

Easily the “girliest” on the list, but with a very significant message for women at any age. Jenna makes a wish on her thirteenth birthday to skip through adolescence straight to becoming a thirty-year-old woman. This wish comes true, but with a catch. She’s still a 13-year-old inside her 30-year-old body with no idea how to navigate this new time in her life.

Though enjoying her new adult freedom, Jenna soon realizes the path she was on before she made her wish has set the stage for how she lives and treats people as an adult. I like that this film articulates that decisions you make in your youth can ripple out into adulthood with irreparable consequences and regrets. Adolescence is awkward and painful at times, but it’s crucial in the process of developing the adults we become. Additionally, the story reminds us of the perpetual truth that we should always choose genuine friendship over fleeting popularity. Dispersed with tubular 80s nostalgia throughout, 13 Going On 30 still brings a big, dimpled Jennifer Garner smile to my face.

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Notting Hill

5b) Notting Hill

It might be a little Mary Sue, (or whatever the male equivalent is), but I’m sure many of us have fantasized at some point in our lives what it would be like to fall in love with someone famous. Though it’s purely coincidental, that’s what happens William Thacker (Hugh Grant) in Notting Hill. Julia Roberts basically plays herself as the acclaimed actress Anna Scott.

I love that Notting Hill explores this idea of what a relationship between a celebrity and the guy next door would really be like. Contrary to the glamor of the movies, this relationship is frustrating and not without grueling effort to hold it together. The British sense of humor and pacing make an otherwise standard yarn fresh and hilarious. You’ll certainly never be able to un-see Rhys Ifans – William’s highly hilarious but inappropriate flatmate – posing in his underwear for the press! 

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Return to Me

4) Return to Me

What happens when you lose your spouse and then, by happenstance, you not only meet the person who received their transplanted heart, but you fall in love with them too? The premise is admittedly far-fetched, but the heart of the story keeps it grounded. Funny lady Bonnie Hunt writes, directs, and plays Minnie Driver’s affable BFF in the film. Now that’s real Hollywood female empowerment!

Roger Ebert said in his review this movie could have been made in 1955, and that’s a commentary to its credit.  However, there is no glossy Hollywood glamor here. Everyone cast in this film feels real, like someone you’d run across at any moment in your own life. I remember my dad chuckling several times because many of the side characters were exactly like his old relatives in Chicago. Minnie Driver and David Duchovny have a beautifully organic love story that gets better every time I watch it.  You’ll be cheering for them from the very moment they meet.

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Roman Holiday

3) Roman Holiday

Though it quite obviously borrowed a lot of elements from my number 1 on this list, it still stands on its own as an endearing and hilarious romp. Roman Holiday was Audrey Hepburn’s debut as a leading lady on screen and she hasn’t fallen from the sky since. She and co-star Gregory Peck were two of the most ridiculously good-looking people of their era and, though very different in personality, they shine brightly together here with childlike playfulness and spirit. Contrary to most romantic comedies, there really isn’t a “happily ever after,” yet somehow you still feel content, as if recalling your own fond memory. The picturesque backdrop of post-war Rome makes an ideal companion to this brief, yet unforgettable storia di amore.

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You've Got Mail

2) You’ve Got Mail

This was my first favorite rom-com. It is a retelling of the 1940 classic The Shop Around the Corner starring Jimmy Stewart, also a great film. In the early days of the internet, with AOL’s famous “You’ve Got Mail” there to greet you after dialing up, two people meet in a chatroom and find each other alluring enough to continue communication through e-mail. Little do they know that they are also business rivals in “real life” and consistently find themselves in a confrontation with each other. 

Tom Hanks and Meg Ryan give us a 1990s version of Mr. Darcy and Elizabeth Bennet, but more than that they defined contemporary rom-com chemistry. Their encounters remind us that our assumptions and judgments of others can often be astronomically wrong. The writing in this film is fantastic with witty dialogue and e-mail exchanges that feel like reading passages of a book. At its core, You’ve Got Mail is essentially a film that is also a love letter to books.

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1) It Happened One Night

It’s common knowledge that most romantic comedies follow a formula. It’s not always a bad thing either. If you were to comb through film history to find the source of the rom-com formula, I would say undoubtedly that it comes from Frank Capra’s fabulous film, It Happened One Night.  This film is THE definitive romantic comedy of all time. I have so many good things to say about it that you can read my entire analysis/review in our Reviewing the Classics series.


Great list! Roman Holiday is my favorite, but It Happened One Night is definitely iconic. I haven’t seen You’ve Got Mail yet, so I might have to try it this Valentine’s Day. Any particular reason you picked more classic movies?

Thanks! You definitely should see You’ve Got Mail, a great V-day choice! It’s super 90s so kind of fun for that reason as well. 🙂 These choices are just my personal favorites in the rom-come genre. To be honest, I’m more of a period piece romance person haha. I tend to cringe at most contemporary setting love stories, but if they have a good center they make the cut. 😉

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