10. Pretty Woman (1990) – Let’s get it out of the way. The opening scene has Julia Roberts driving a stick shift Lotus Esprit, which is still one of the coolest super cars ever built. Another scene to look out for is Jason Alexander trying to mount Julia Roberts after discovering she’s a hooker. I don’t think this scene would make the final cut in today’s light-hearted romcoms. It gives the movie a lot of real weight and that’s why it’s on the list.
9. While You Were Sleeping (1995) – The dramatic irony in this movie is what many of the new chick flicks don’t have enough of. It’s a very sharp movie that guys will enjoy for it’s clever story telling. Sandra Bullock, of course, nails it with her comedic timing and effortless charisma. This is probably one of the most under appreciated romantic comedies out there.
8. Dirty Dancing (1987) – This goes on the list because it is the female version of the Karate Kid. Instead of Mr. Miyagi taking Daniel from boyhood to manhood, it’s Johnny taking Baby from girlhood to womanhood. Patrick Swayze pretty much plays the same character as in Point Break, but instead of surfing it’s dancing. Guys can root for him because the character Johnny is a bad ass.
7. Edward Scissorhands (1990) – I saw this as a child and many times after that as a teenager and then recently again. The movie tells the story of unconditional and selfless love, but has a dark edge to it which makes this fantasy love story believable. Danny Elfman’s score can seduce any guy into watching this movie too. The style of music is just too familiar for any guy in his late twenties or early thirties to turn down.
6. An Affair To Remember (1957) – Which guy doesn’t want to learn from Cary Grant playing a millionaire playboy? Grant was the original George Clooney. The movie (which is a remake) was remade again with Annette Bening and Warren Beatty, but their chemistry doesn’t compare to what Cary Grant and Deborah Kerr had. It’s also the movie that Sleepless and Seattle keeps referencing.
5. The Graduate (1967) – A perfect movie about a boy finding himself in a very plastic world. It’s sexy with the whole Mrs. Robinson thing, sweet when Dustin Hoffman starts finding himself and beautiful when he goes after her. It’s a classic for a reason.
4. 500 Days of Summer (2009) – Why does this go so high up on the list? I think it’s because it’s been sooooooo long since there was a romantic comedy with any depth to it. I get there are dramas with depth out there, but this was a romantic comedy post mid 90s that both guys and grown ups could watch and relate too. The soundtrack is perfect and there’s something so vibrant, yet classic about this movie’s charm.
3. A Roman Holiday (1953) – There are many other later movies Audrey Hepburn is better known for, but Gregory Peck brings out her best in her first ever movie. Peck’s character starts out selfish like any bachelor living overseas would be, but his character grows with love. It’s black and white, but in my opinion, one of the best looking movies of all time. It’s also the first movie where product placement (Vespa scooter) started.
2. How To Steal A Million (1966) – A heist and a love story? Come on! Audrey Hepburn and Peter O Toole are perfectly matched in wit and charm. They both keep their secrets from each other and have to work together following a perfect romcom formula before it became the formula. Peter O Toole also drives the best looking car in the world in this movie, the Jaguar XKE. I could have named Sabrina or Breakfast and Tiffany’s, but the heist just makes this movie way too damn cool.
1. Annie Hall (1977) – Perfect movie. Guys will also deeply relate to this because Woody Allen’s character speaks from the heart as a man who just doesn’t understand relationships or women.