I’m a sucker for a good romantic comedy.  I think it’s because I feel some of the best humor stems from the male/female dynamic.  (Stand-up comics have been fishing from that well since caveman days.)  Plus, I’m a big softie.

But I think they’ve taken a bad rap over the last few years.  They’re usually lumped in as “chick flicks” and dismissed as little more than an easy Hollywood cash-in.  And with good reason – I mean, just how many bad movies can Katherine Heigl, Sarah Jessica Parker, and Ashton Kutcher make?  Then there’s contrived plots, ridiculous dialogue, leads with no chemistry, little or no laughs…you get the picture.

But there really are some good romantic comedies (henceforth referred to as “rom-coms”) out there, and I’d like to share some of my favorites.


ANNIE HALL (1977) D: Woody Allen.  Woody Allen, Diane Keaton

Woody’s done many good rom-coms, but this is my favorite. Numerous classic lines and scenes, inventive direction, and even a little animation thrown in.  A rare Oscar-winner for the genre.

He Gets The Girl: No

Would I Date Her: Probably not; a little too much of a ditz


(500) DAYS OF SUMMER (2009) D: Marc Webb.  Joseph Gordon-Levitt, Zooey Deschanel

What impresses me most is the interesting way the film jumps around in time, chronicling the 500 days of the relationship.  If you’re a guy and have ever had your heart broken, you need to see this.  Oh, and it’s quite funny.  And there’s Zooey.

He Gets The Girl: No

Would I Date Her: OMG YES


WHEN HARRY MET SALLY (1989)  D: Rob Reiner.  Billy Crystal, Meg Ryan

One of the first modern R-rated rom-coms, and usually a movie that comes to mind when people think of the genre.  Some great lines and great relationship insights.  And could Meg be any cuter?

He Gets The Girl: Yes

Would I Date Her: Yes, but mostly for her looks


SHAUN OF THE DEAD (2004)  D: Edgar Wright.  Simon Pegg, Kate Ashfield

Really more of a rom-zom-com, but you have to admire all the shit Shaun goes though to get Liz back.  Honestly, you should see any movie Wright directs.

He Gets The Girl: Yes

Would I Date Her: Maybe, if she didn’t nag too much


GOUNDHOG DAY (1993)  D: Harold Ramis.  Bill Murray, Andie MacDowell

This one’s a little unique in the sense that the guy doesn’t really have any interest in the girl, but must win her over to break the déjà-vu thing.  A clever premise pulled off very well.  And can you picture anyone else but Mr. Murray as the obnoxious Phil?

He Gets The Girl: Yes

Would I Date Her: Nah.  Too full of herself and kind of horse-facy


CHASING AMY (1997)  D: Kevin Smith.  Ben Affleck, Joey Lauren-Adams

I don’t like this movie because of the “turning a lesbian” theme, I like it because I think, when he wants to, Kevin Smith can write some great dialogue.  And I certainly can see where Holden would fall for Alyssa – she’s just so cool and adorable.  The scene in the car where Holden confesses his feelings chokes me up every time.

He Gets The Girl: No

Would I Date Her: You bet your sweet ass


BIG (1988)  D: Penny Marshall.  Tom Hanks, Elizabeth Perkins

Love story with a twist: a 12-year-old turns into a 30-year-old and finds he’s a hot property with a coworker.  Lots of laughs and genuinely touching moments.

He Gets The Girl: No

Would I Date Her: No, too much of an uptight yuppie


TUCKER AND DALE VS EVIL (2011)  D: Eli Craig.  Tyler Labine, Katrina Bowden

Not only is this film hilarious (I love the premise), but if you look past the comedy gore, it’s got a real sweet heart, with the message that people are more than their outward appearance.

He Gets The Girl: Yes

Would I Date Her: In a goddamned heartbeat


SOME LIKE IT HOT (1959)  D: Billy Wilder.  Tony Curtis, Marilyn Monroe

Not just a great rom-com but a fantastic comedy all around.  Tony Curtis and Jack Lemmon in drag, multiple deceptions/love interests, a bona fide sex goddess, and one of the funniest closing lines ever.

He Gets The Girl: Yes

Would I Date Her: Is this a trick question?  It’s MARILYN MONROE


AIRPLANE! (1980)  D: Jim Abrams, Jerry Zucker, David Zucker.  Robert Hays, Julie Hagerty

I know, Airplane!’s a silly parody, but Ted Striker shows real guts.  He faces his demons, lands the plane, wins one for the Zipper, and gets the girl back.  And if you don’t think this movie is funny at all, you and I are going to have to take it outside.

He Gets The Girl: Yes

Would I Date Her: No, a little too flighty (pun intended)


THERE’S SOMETHING ABOUT MARY (1998)  D: Bobby Farrelly, Peter Farrelly.  Ben Stiller, Cameron Diaz

The Farrelly brothers are pretty hit-or-miss, but this film hits.  Sure, it’s goofy and often goes for the cheap laugh, but you really feel for Ted’s quest to reconnect with Mary.  Bonus: Brett Favre.

He Gets The Girl: Yes

Would I Date Her: Yes – there’s something about her


THE 40-YEAR-OLD VIRGIN (2005)  D: Judd Apatow.  Steve Carell, Catherine Keener

Started a resurgence of “raunchy” but well-made, well-written rom-coms.  I still laugh at this film a lot.  And Ms. Keener is such a MILF (or, in the movie, a GILF).

He Gets The Girl: Yes

Would I Date Her: Yes yes yes


FORGETTING SARAH MARSHALL (2008)  D: Nicholas Stoller.  Jason Segel, Mila Kunis

Another fine film from the Judd Apatow crew.  Funny stuff, lots of scantily-clad beach women, and Mila Kunis’ character steals your heart.

He Gets The Girl: Yes

Would I Date Her: Date, marry, worship, lick the boots of, etc.