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The Top 9 Romantic Comedies for Dudes

The Five-Year Engagement

Relationships can turn us into self-involved, sentimental wrecks. But throw on a good romantic comedy and suddenly it's tough to take yourself too seriously. With life back in perspective, you laugh away your tears and regain the certainty that love will conquer all.

Well, unless you're a guy.

Men seem more immune to the mirror these movies hold up, perhaps because they rarely see themselves reflected. It's the infrequent film that makes a guy nod his head and say "Yup, that's me in love. Aren't I silly?"

Because the hilarious new flick "The Five-Year Engagement" fits the bill, here are our favorite rom-coms that aren't just for chicks.

9. '(500) Days of Summer' (2009)

Fox Searchlight

In a bit of postmodern role reversal, Tom (Joseph Gordon-Levitt) is a hopeless romantic who's sure that true love is his only shot at happiness. Zooey Deschanel plays Summer, a pragmatist who doesn't believe true love exists. As Tom retells the story of their doomed romance to his friends, his memories and self-deceptions are displayed before us in all their fantastical, musical and surrealistic glory. If "Annie Hall" and "Glee" had a baby, it would be this -- and it would be a dancing baby.

8. 'Some Like It Hot' (1959)

Billy Wilder's classic screwball comedy asks the question: Would you dress up like a woman for a few of weeks for a shot at Marilyn Monroe? Had it been any other actress, the premise might not have flown. But it's Marilyn Monroe. So we totally get why Jack Lemmon and Tony Curtis dress in drag, trip in heels and suffer endless come-ons from dirty old men, just to steal a few more moments with the blonde bombshell. This pic is often cited by film theorists for its subversive, cross-dressing, subtextual implications. But for most audiences, it's just funny seeing Jack Lemmon in lipstick.

7. 'Forgetting Sarah Marshall' (2008)


Jason Segel plays a broken -- often nude -- man in this underrated gem marking Russell Brand's (and Segel's penis's) debut on the big screen. After being dumped by his TV star girlfriend, Sarah (the lovely Kristen Bell), Segel takes a consolatory trip to Hawaii. But Sarah happens to be staying at his hotel with Brand -- the sort of VD-infused sex god every guy has nightmares about his girl hooking up with. It's hard not to love Segel, who isn't afraid to play the sad sack we've all been at one time or another. And it's hard to get over his awesome Dracula rock opera with puppets.

6. 'Roxanne' (1987)

A must-watch for males disenchanted with romance. Steve Martin proves language is the key to a woman's heart, even when the poet's saddled with the world’s biggest schnoz. Daryl Hannah is elegant as the beautiful Roxanne, who thinks she's hot for a hunky fireman, but learns the frilly words he seduced her with were fed to him by his long-nosed co-worker. An added bonus is that guys watching this flick can feel super classy 'cause the story's based on the French play "Cyrano de Bergerac." And French stuff is super classy.

5. 'Annie Hall' (1977)

If you don't get Woody Allen's opening joke about not wanting to belong to any club that would have you as a member, then "Annie Hall" isn't for you. Allen resembles what a man's super-ego might look like if it grew limbs and purchased some glasses. And his obsessive dissection of his relationship with the wonderfully scatterbrained Annie (Diane Keaton) is an acquired taste. But if you're the type who too often feels with his head instead of his heart, nothing will help you laugh your way through a break-up like this Academy Award-winning masterpiece.

4. 'The Wedding Singer' (1998)

New Line

When it's boys-night-in (Wednesdays, traditionally), this Adam Sandler/Drew Barrymore '80s flashback is sure to please the fellas. Few dudes can resist curling up on the couch in their jammies and singing along with Sandler as he ruins weddings with tunes of bitterness and despair. And let's not forget Barrymore, who was at her scientifically confirmed zenith of adorkableness, resembling a sort Tweety Bird. And just when you thought it couldn't get better, that grandma performs "Rapper’s Delight."

3. 'When Harry Met Sally' (1989)

Billy Crystal gave up the male race's secret that all men want to sleep with every female friend. And never before has a movie led to so many awkward conversations in the car ride home from the theater. Meg Ryan gave up the female race's secret that all women fake orgasms. And never before has a male audience so enjoyed a point being proven. Sometimes honesty needs to be screamed -- and moaned a little.

2. 'There's Something About Mary' (1998)

This Farrelly Brothers tour de force might best be remembered for its outrageous scenes of zipper-meets-testicle mishaps and canine CPR miracles. But it's far superior to other gross-out films of its day. At its core lies the sweet story of a sentimental guy (Ben Stiller) who refuses to end his search for his high school crush, even after being falsely informed that she's a 250-pound, wheelchair-bound mail-order bride. Cameron Diaz shines brightly at the center of the film, and it's easy to understand why Stiller must compete with every creep under the sun (including that perv, Brett Favre) to win her affections. It's the rare comedy that can be earnestly high-minded and hilariously lowbrow at the same time.

1. 'High Fidelity' (2000)

Buena Vista

Rob (John Cusack) and Barry (Jack Black) work at a record store and waste innumerable hours ranking music as if taste could be accounted for (yes, like we're doing here...). When Rob's girlfriend leaves him, he acts like a guy. He begs for her to return, even though he wanted to see other people. He sleeps with Lisa Bonet (who wouldn't?) but is filled with sanctimonious rage upon learning his ex is shagging Ray (Tim Robbins), a cheesy guru who's into tantric sex and world music.

By the conclusion, Rob's back with the girl and makes her a mixtape she'll like, rather than imposing his own tastes. This small leap of maturity feels representative of the real life self-improvements men hope to make. And it's this realism, along with its wit, that makes "High Fidelity" a favorite amongst menfolk everywhere.

Originally published Nov. 24, 2011.

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