Ten Modern Romantic-Comedy Classics

The Romantic-Comedy is often a genre ridiculed for its predictable ending and its focus on romantic fantasy. But it's actually quite misunderstood. For one thing, every genre movie (horror, gangster, western, sports) relies on certain audience expectations and they're "all the same". Even though the ending may be predictable (the couple gets together or they don't), the middle of the film can often be funny, romantic and surprisingly insightful. So here are my favorite modern romantic-comedies. And by modern, I mean within my lifetime. 

10.  Nick and Norah's Infinite Playlist - 2008

(Peter Sollett; Kate Dennings and Michael Cera)

Taking place in 24 hours, this film is a beautiful look at New York City nightlife but all the places you don't see. The cast is fantastic times 12. Dennings is a beautiful surprise and this is Michael Cera's final good performance as the Awkward Teen. After this movie, it was too much. The three guys and two girls who make up the supporting cast are just top-notch. The theme of music bringing people together and how some people can chase the impossible is deep, which is what makes this teen romance so great. 

9. While You Were Sleeping - 1995

(Jon Turteltaub; Sandra Bullock and Bill Pullman)

Sandra Bullock's breakout movie has stood the test of time more than any other 90s rom-com. I don't know what it is about this infectious comedy but it always seems fresh even 15 years later. Bill Pullman makes an excellent hero. He's funny and charming but not too perfect. The Peters Boyle and Gallagher lead the wildly funny supporting cast. Of course, Sandra is Sandra. 

8. Hitch - 2005

(Andy Tennant; Eva Mendes, Will Smith, Amber Valletta and Kevin James)

Usually, the heroes in romantic-comedies are suave, charming and sexy. But what if some men need help becoming that guy? This movie is a fun look at the unlikely romantic-comedy hero, played by Kevin James. Will Smith delivers a star turn and Eva Mendes gets to be more than just sexy. Hilariously enough, this is the last good movie any of the four cast members made but "Hitch" is re-watchable enough to satisfy everyone. 

7. He's Just Not That Into You - 2009

(Ken Kwapis; Ginnifer Goodwin, Justin Long, Jennifer Aniston, Ben Affleck, Drew Barrymore, Kevin Connolly, Scarlett Johansson, Jennifer Connelly, Bradley Cooper)

Man, the female cast in this movie is amazing and beautiful. Goodwin, as the heart of the movie, is spectacular as the film smartly portrays her desperation as a courageous and perseverant search for love. Affleck and Cooper are the only males who leave a mark. The film is an interesting look at several classic relationship stories (friends-become-lovers, the bored married couple, etc). I particularly liked Affleck and Aniston's storyline and they were great together. 

6. How to Lose a Guy in 10 Days - 2003

(Donald Petrie; Kate Hudson and Matthew McConaughey)

This is one of the two Matthew McConaughey movies I will defend (the other is the fun but inferior "The Wedding Planner"). This battle-of-the-sexes screwball comedy is vitalized by a full-bodied comedic performance from Kate Hudson. Everything she does is just wonderful in this movie. "Our love fern... YOU LET IT DIE!!!" is just one of the many examples of her awesomeness. Matthew provides a fine sparring partner but he's overshadowed by her. It's not his fault, it's the script. But for once, the girl is the doer and the guy is the reactor. Usually, it's the other way around. 

5. The Proposal - 2009

(Anne Fletcher; Sandra Bullock and Ryan Reynolds)

Whoever thought to put these two together in a comedy needs to win a Nobel Prize. And whoever thought to throw in Betty White is my best friend. The film is full of supremely funny moments like the "giving thanks" scene and when Margaret and Andrew "run into each other". And it showed an older woman with a younger man which is amazing and progressive. 

4. Something's Gotta Give - 2003

(Nancy Meyers; Diane Keaton and Jack Nicholson)

While objectively this film is better than "The Holiday", it's also about old people which makes it a little hard to relate to. Of course, that doesn't stop it from being a wildly successful movie. Jack & Diane are absolutely brilliant together and the supporting cast is fantastic especially Amanda Peet. The only problem this movie has is that it feels long even though it's 7 minutes shorter than "The Holiday". 

3. (500) Days of Summer - 2009

(Marc Webb; Zooey Deschanel and Joseph Gordon-Levitt)

If Quentin Tarantino ever made a romantic-comedy, well, it would look a lot like this one. "(500) Days" employs a nonlinear storyline which, coupled with the promise that the lead pair will NOT end up together, makes this film an edgier cousin to the standard romantic-comedy. With 3-dimensional characters, fresh observations about young life and the most charming lead pair ever, this film is just perfect. Unfortunately, it was almost too new age for  Oscar voters but that's another story. 

2. The Holiday - 2006

(Nancy Meyers; Cameron Diaz, Jude Law, Kate Winslet and Jack Black)

I love this movie so much that I watch it every month. And it strangely seems to get better every time. See, when you have a movie that's basically two movies in one with two protagonists, the trick is to write each story in a different way. Nancy Meyers succeeds immensely. Diaz and Law share a passionate, intense and semi-tragic love affair that brings up many issues (his children, her business, their commitment fears). But Winslet and Black have an easy, breezy, beautiful friendship that only turns romantic at the end. But the best thing about this wonderful romance: it has an open ending. Meyers doesn't promise that either couple will survive; the film just ends on a happy note at the end of the characters' holiday. 

1. When Harry Met Sally... - 1989

(Rob Reiner; Meg Ryan and Billy Crystal)

This is the ultimate romantic-comedy. In fact, you'll notice that this is the only film before 1995 that appears on this list because no list of rom-coms is complete without it. Perfectly casted, Insightful, sharp, hilarious and hugely romantic, this film is a staple of the genre and of Hollywood itself. So many classic lines and classic moments that, surprisingly, still hold up when you watch them. Honestly, this film can be watched over and over. Oh, and when Sally tells Harry she hates him but really she means she loves him, it's a perfect ending to a wonderful picture. 

So there you have it, my favorite romantic comedies of the last 21 years. Some honorable mentions:

-The Wedding Planner

-Zack and Mini Make a Porno

-Up in the Air

-Pretty Woman

-What Women Want

Hope you enjoyed it!