The 40 Year Old Virgin
Did I hate “Knocked Up” enough to put me off Judd Apatow for good? Nah… Actually, I wasn’t sure if I wanted to put this or “Forgetting Sarah Marshall” on this list… Maybe make it a double feature.
The Baxter
Michael Showalter wrote and directed this underrated, cute, nerdy, and actually petty damn funny romcom and stars with Elizabeth Banks, a brunette Michelle Williams, and Justin Theroux.
Bringing Up Baby
Having spent several years of my childhood completely obsessed with Madonna, I learned enough Material Girl trivia to know that the brilliantly terrible Who’s That Girl? was loosely based on this 1938 film. It took me many years and dozens of viewings of the Madonna and Griffin Dunne classic to actually get around to seeing the Hepburn/Grant predecessor. I love it. And I still can’t help being surprised when old movies actually make me laugh.
Down With Love
Down With Love is a silly parody of all the screwball sex comedies of the 60s, complete with amazing costumes, over-the-top double entendres, and amazing sets. Get over your Zellweger hate.
Gentlemen Prefer Blondes
Even without the famous “Diamonds are a Girl’s Best Friend” scene (re-immortalized years later in the “Material Girl” video), this movie would be spectacular: it’s funny, it’s silly, it’s a musical, it’s entertaining, and it’s a classic romcom in every way, complete with a (spoiler alert) double wedding at the end.
The Intern
The Intern, starring Dominique Swain in the title role at the fictional New York glossy Skirt, is totally underrated as a guilty pleasure romcom. Yes the writing is sub-par, the plot fairly cliché, and the jokes predictable, but it’s still sooo good! Joan Rivers is awesome and the fashion world references and cameos (Gwyneth Paltrow, Tommy Hilfiger, André Leon Talley) are plentiful.
Kissing A Fool
Watching this movie recently for the first time in several years, I was surprised to see that it was written by James Frey. Weird. Synopsis: David Schwimmer’s character is engaged to a woman, starts to freak out and worry that she’ll cheat on him so enlists neurotic best friend, played by Jason Lee, to try and sleep with her. All sorts of mess ensues. Poorly written, poorly acted, poorly executed, and I watch it whenever I need a romcom fix. Go figure.
Pretty In Pink
I will always be pissed at Molly Ringwald’s character for turning her awesome boss’s cute 60s style prom dress into a pillowcase, but this movie is a true classic—it even shows actual tracks to represent the class divide! Ducky is the Screech to Andie’s Lisa. James Spader’s portrayal of asshole Steff is genius. Andrew McCarthy even rocks.
There’s Something About Mary
This is easily one of my favorite movies of all time, romcom or otherwise. I never feel like not watching this movie.
The Wedding Singer
This movie has everything you could want in a romantic comedy: Billy Idol, hands full of meatballs, a DeLorean, hilarious misunderstandings that all get worked out in the end, moonwalking, mullets, and, of course, Sandler and Barrymore, a match made in romcom history (full disclosure: I even liked 50 First Dates)!
Runners Up: Annie Hall, Better Off Dead, Clueless, Desperately Seeking Susan, The Graduate, Love Actually, Sabrina, Fool’s Gold
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This is sooo cool! I’ve been looking for a list of movies to watch when I’m too tired to deal with anything too highbrow. Great post.
I love “Down with Love”… totally forgotten about!