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The Top 10 Movie Wingmen

The dating scene is brutal, but we have a feeling that we’d have a lot more success with the ladies if any of the guys on this list were on our side.

10. Stiles (Jerry Levine), Teen Wolf
The perfect wingman wants you to succeed. And if he benefits in the process, all the better, which makes Jerry Levine’s wheelin’ and dealin’ Stiles the ideal candidate. Need to blow off steam while catching street waves? Stiles will pilot the van — and loan you his Hawaiian shirt. Hungry for some Jell-O? Stiles is quick to dump it down a beautiful girl’s shirt, giving you ‘Seven Minutes In Heaven’ to devour that snack. Now, he can’t get you a keg of beer. But if you happen to turn into a Teen Wolf, Stiles will be the first one cheering for you from the bleachers… and selling a t-shirt that bears your hairy likeness. Sean O’Connell

9. Randall ‘Pink’ Floyd (Jason London), Dazed and Confused
When Randall ‘Pink’ Floyd takes Mitch Kramer (Wiley Wiggins) under his wing in Richard Linklater’s 1993 ode to the seventies, Mitch has just been mercilessly ass-paddled by Pink’s friends. But by the end of the night, thanks to Pink’s guidance, Mitch is tight with almost all of them (and probably the hippest high school freshman-to-be in history). As much mentor as wingman, Pink introduces Mitch to booze and weed and, not neglecting his more traditional wingman duties, gives him sage advice on how to hook up with the object of his desire: ‘Tell her we left you. It’ll work.’ And it does. David Thomas

8. Mike Damone (Robert Romanus), Fast Times at Ridgemont High
A helpless nerd could do a lot worse than having the local ne’er-do-well-slash-ticket-scalper showing you the ropes on how to deal with the ladies. (Rule #2: ‘You always call the shots: ‘Kiss me. You won’t regret it.”) The again, Mike will probably sleep with your girlfriend, get her pregnant, and not even have the decency to pick her up after her abortion — so you might be better off playing side one of Led Zeppelin IV with your gal in the next town over. Christopher Null

7. Will Hunting (Matt Damon), Good Will Hunting
A good wingman doesn’t just help his friend get digits; he also has his friend’s back when the competition gets ugly. When his working-class best friend Chucky (Ben Affleck) gets cock-blocked by a pompous Harvard douche, Will defends his slighted buddy by delivering one of the most devastating verbal bitchslaps in cinematic history, complete with historical insight and a soul-shattering revelation. He defends his friend, demolishes the competition, and gets a phone number. How do you like them apples? Pete Croatto

6. Jay (Romany Malco), Dave (Paul Rudd), and Cal (Seth Rogen), The 40-Year-Old Virgin
‘Your dick is my dick,’ Jay says to geeky, grown-up virgin Andy (Steve Carrell), a mission that’s embraced by fellow Smart Tech co-workers Dave and Jay. The trio does everything in its power to get Andy in the game, from speed dating to (unknowingly) hiring a transvestite hooker. But with all of their misguided efforts, the trio provides a valuable lesson: If you want to get the girl, sometimes you have to fly solo. PC

5. Enid (Thora Birch), Ghost World
Say you’re a borderline shut-in with a passion for vinyl records and chicken shack memorabilia. How exactly are you going to meet the girl of your dreams? Perhaps a vaguely goth misanthropic teenager can help. Ghost World‘s Enid starts out by pranking poor Seymour (Steve Buscemi) but ultimately becomes close friends with the guy, guiding him step by step — with mixed results — through the convolutions of modern-day courtship rituals… rituals which, it turns out, neither of them seem to fully understand. CN

4. Jack (Thomas Haden Church), Sideways
OK, so he’s not a saint. In fact, it’s hard to even classify Jack as a human being. He’s closer to being an erection with appendages and great hair. (Cheating on your fiancée is one thing, but days before your wedding? With two women?) Best man Miles (Paul Giamatti) may distance himself from his longtime friend, but the philandering Jack is a life saver. Miles is so cautious, so beaten down by life, that he can’t see a good thing that’s right in front of his face — in this case, the stunning Maya (Virginia Madsen). Jack gets Miles back into the world of the living, even if the example he sets is absolutely reprehensible. PC

3. Roger Swanson (Campbell Scott), Roger Dodger
As a hapless kid in the big city, you can’t ask for better help in the love life department than to have a randy uncle who’s willing to share everything he knows with you about the fairer sex. Campbell Scott is that uncle, teaching young Nick (Jesse Eisenberg) on the intricacies of the female mind (‘Do you think women have a clue what goes on up here? What do they think, it’s all stock quotes, drill bit sizes? They don’t know shit! Let’s keep it that way.’) and how to get a sneaky eyeful of exposed skin without getting busted (‘Remember, angle of incidence equals angle of reflection. In other words, if you can see them, they can see you.’). Roger’s lessons may not get Nick very far in the end, but in this case, education is its own reward. CN

2. Trent (Vince Vaughn), Swingers
Let’s be honest: If Jon Favreau’s Mike barhopped with us, it’d take about 25 minutes of his whining before we made up an excuse and ditched him. But Trent, God bless him, lifts his friend over his self-flagellation and does it in style, whether it’s picking up a casino waitress or kicking ass at video hockey. Part friend, life coach, and honorary Rat Pack member, every guy needs someone like ‘Double Down’ in his corner. If he helped a pile of self-doubt like Mike get a dish like Lorraine (Heather Graham), think how we’d succeed. And think how much fun we’d have along the way. Who’s the big winner? PC

1. Goose (Anthony Edwards), Top Gun
You may not know wingman-extraordinaire Lt. Nick Bradshaw by his name, but you almost certainly know him by his call sign: Goose (Anthony Edwards). While the top gun of 1986’s Top Gun was undoubtedly Maverick (Tom Cruise), it was Edwards’ plain looks and goofy affability that highlighted Cruise’s leading-man resplendency. In so doing, Goose provides a model for future wingmen, the example all others aspire to match. Whether he’s lending his voice to a rendition of ‘You’ve Lost that Lovin’ Feeling’ to help Maverick pick up a chick at a bar, or martyring himself in an attempt to help Maverick prove he’s the best of the best, Goose’s loyalty to his leading man — and his status as the ur-wingman — is never in question. Matt McKillop

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