Top 10 Old School Rom Coms

In honor of Valentine’s Day, we’re rerunning a series of top ten lists dedicated to the film-genre equivalent of those little heart candies: the romantic comedy. Our first was classic rom coms; second was alternative love stories; next we listed the best overlooked ones. Today, we continue with old school classics made before we were born. We haven’t actually seen all of these — this list is more aspirational, based on movie reviews and recommendations we’ve culled from various sources (friends, family, Rotten Tomatoes, movie nerds…). You know, these are the ones we feel like we should get around to Netflixing at some point. Up til now we’ve stood by our original selections, but we’ve altered this list slightly based on your recommendations.

  1. It Happened One Night (1934) – You’ve heard of director Frank Capra? Well this was one of his babies. It was the first movie to receive all five major Academy Awards: Best Picture, Best Director, Best Actor (Clark Gable), Best Actress (Claudette Colbert), and Best Adapted Screenplay. ‘Nuff said.
  2. Top Hat (1935) – Ginger Rogers and Fred Astaire dance their way to love in this musical comedy of mistaken identity which features some of Irving Berlin’s best songs.
  3. Bringing Up Baby (1938) – Cary Grant is the straight-laced scientist and Katherine Hepburn is the zany free spirit. Together, they go in search of a lost leopard named Baby and fall in love along the way. The term “screwball comedy” usually sends up red flags, but perhaps it meant something different way back when.
  4. The Philadelphia Story (1940) – First it was a Broadway hit with Katherine Hepburn. According to Rotten Tomatoes, “she acquired the screen rights, claimed the starring role, and chose the director [George Cukor], screenwriter, and lead cast,” which includes Cary Grant and Jimmy Stewart (in an Oscar-winning role). Pretty cool.
  5. His Girl Friday (1940) – Another “screwball” comedy starring Cary Grant. This time, it’s a battle of the sexes between him and Rosalind Russel. According to Rotten Tomatoes, it’s got some of “the fastest dialogue ever filmed (peppered with inspired ad-libbing by Grant and Russell, each appearing at comedic high points in their careers).” We’d like to see a remake: “My Boy Monday.”
  6. The Lady Eve (1941) – Barbara Stanwyck is a con artist, after geeky Henry Fonda’s fortune, who accidentally falls in love.
  7. Singing in the Rain (1952) – It’s considered the best American musical of all time, so there’s got to be more to it than just that titular scene starring Gene Kelly. Trivia tidbit: They put milk in the rain water so it’d show up better on film.
  8. Roman Holiday (1953) – Audrey Hepburn gets her big break as a princess on the lam who falls for newspaper man Gregory Peck. She wins the Oscar for best actress and the rest is history.
  9. Breakfast at Tiffany’s (1961) – Audrey Hepburn is Holly Golightly, the stylish main character in Truman Capote’s New York novella, which Blake Edwards adapted (beyond recognition) for the big screen. The girl knows how to throw a party.   Holiday (1938) – We were convinced by Lyz’s argument against Breakfast at Tiffany’s  and PK’s push for this movie’s inclusion, since Rotten Tomatoes says this film with Katherine Hepburn and Cary Grant pretty much “stablished the rules for intelligent romantic comedies.”
  10. My Fair Lady (1964) – The musical version of George Bernard Shaw’s 1913 play Pygmalion starring — you guessed it — Audrey Hepburn that won 8 Oscars, including best picture, best director (George Cukor), best actor (Rex Harrison as Professor ‘Enry ‘Iggins), best music (Andre Previn), best costume design and set decoration (Cecil Beaton). It does have some seriously amazing hats in it.

Want something a little more modern?
Top 10 Classic Rom Coms


  1. Thank you SO SO SO much for including Top Hat! It’s hands down one of the most genuinely romantic comedies I’ve ever seen. It has great dancing, and you’re right about Berlin’s greatest hits! And Fred Astaire? so dreamy!!

    Thanks Ladies!!!

  2. The definition of comedy is that the two young lovers “get each other” at the end – it doesn’t require marriage, or even permanence, just being together at the end.

    This is a great list! Only two have I not seen, and I’m Netflixing them right now! Thanks! 🙂

  3. What about “Sabrina”? That’s another Audrey Hepburn classic and, I’d argue, more of a romantic comedy than “Breakfast at Tiffany’s”.

  4. Great list! Some of my personal favorites made it. I’m a huge fan of Katherine Hepburn and Cary Grant. One of their lesser known films, perhaps because there was less comedy in it, I think should receive some consideration. Holiday was, I think, their first film together and is brilliant.

  5. I quibble with the fact that breakfast at tiffany’s qualifies as a rom-com. While there are some lighter moments in it, it is a dark love story that has a complicated and sad ending. Not your standard rom-com. Isn’t the definition of comedy that someone gets married in the end? I don’t think this qualifies. But is a lovely movie even though its nothing like the book. Which is also My Fair Lady. Nothing like Pygmalion!

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