Image via Complex Original
It's impossible to say who was the first wingman. It could have been Cupid when he shot his first arrow at a helpless romantic. Or maybe it was when Odysseus told Menelaus, “Dude, I got your back,” when they went to bring back Helen of Troy. In movies, the wingman (or wingwoman) has always been there, steering the stars of the film through the ups and downs of love, but the wingman really busted into the pop culture forefront with characters like Vince Vaughn in Swingers, making waiting six days before calling an unofficial rule. After that, the wingman became a staple of Hollywood comedies with Jason London in Dazed and Confused, Jason Segel in I Love You, Man, Leslie Mann in Knocked Up, Paul Rudd in The 40-Year-Old Virgin, Ryan Gosling in Crazy, Stupid, Love, and Jason Sudeikis in Hall Pass, just to name a few. But although there have been many, only a few can be called the best. Here’s a look at The Best Wingmen (and Wingwomen) in Film History.
Anthony Edwards in Top Gun
Nick “Goose” Bradshaw (Anthony Edwards) is literally a wingman to Pete “Maverick” Mitchell (Tom Cruise). As his flight partner in Top Gun, he plays support to Maverick on air, ground, and the volleyball court. Goose is even a respectable enough wingman to be the only one wearing a shirt for the iconic and totally ridiculous volleyball scene. He steps up beyond setting for the spike when he sings backup on “You’ve Lost That Lovin’ Feeling” so that Maverick can get the girl. It’s hard for future wingmen and wingwomen to meet the high standards set by Goose.
Bill Hader & Seth Rogen in Superbad
The police may be there to protect and serve, but playing wingman is not part of their job. In Superbad, Officers Slater and Michaels (Hader and Rogen) team up to show Fogell (Christopher Mintz-Plasse) that cops are not only cool, but they can help you get the girl. In one night, Fogell goes from nearly getting busted for using his McLovin fake ID to teaming up with Slater and Michaels as they make arrests, get drunk, shoot guns, and peel off donuts in empty parking lots. Their true wingmen skills shine through when they agree to fake arrest Fogell just to make him look like a super badass in front of his crush.
Campbell Scott in Roger Dodger
This movie might as well have been titled My Uncle, My Wingman. Seriously, the entire plot to Roger Dodger is Roger Swanson (Scott) coaching his nephew Nick (Jesse Eisenberg) on the ways of women and doing everything that he can to get him some action. Scott drops deadpan pick-up artist science on Eisenberg, most of which comes off as vaguely misogynistic pages taken from The Game. The best lesson Roger teaches his nephew? Sometimes it doesn’t pay to be a playboy.
Jack Lemmon in The Apartment
Playing the wingman for your boss is one way to try and climb the corporate ladder. Bud (Lemmon) tries to please his by letting them use his New York apartment for their extramarital affairs. Yeah, that’s right. Bud keeps his office drone job by letting the higher-ups use his place as their bachelor pad. No one said that being a wingman was easy. The Apartment’s premise reads more like a Mad Men episode than a feature film from the 1960s, but Bud proves that paying your wingman dues can get you the leading lady.
Christina Applegate in The Sweetest Thing
We should all have a friend like Courtney Rockcliffe (Applegate) in The Sweetest Thing. You know, someone who will road trip with you to a wedding of some stranger that you just met in order to tell them how you really feel. We’ve all been there, right? Hey, a good wingperson will support you no matter how foolhardy the romantic situation—even when those situations involve exploding toilets and glory holes.
Alicia Silverstone in Clueless
Alicia Silverstone’s Cher defined a generation of wingwomen. Actually, being that Cher is based on Jane Austen’s Emma, her character is almost the blueprint for the wingwoman. Silverstone made it possible for moviegoers to love a previously hated movie character stereotype: the vapid, rich Valley girl. She uses her charm to turn matchmaker after successfully setting up a pair of teachers. Cher then turns her sights on Tai (Brittany Murphy) to prove that she can turn even the most lost of causes around. It all goes well until Cher realizes that she and Tai like the same guy. Then again, doesn’t everyone like Paul Rudd?
Hayley Mills in The Parent Trap
For most of us, The Parent Trap was our first experience of successful winging—in this case, wingchildren. Twins separated at birth by their parents’ divorce meet at summer camp and decide that they need to rekindle that romance. The twins, both played by Hayley Mills, need to act fast before their father marries his gold-digging fiancée. Because it’s a Disney movie, it all works out just fine, but the older you get the more you can’t help but wonder what made these parents get a divorce right after their kids were born, and why’d they keep it a secret. You’re sure to have darker questions if you grew up with the Lindsay Lohan version.
Sarah Michelle Gellar in Cruel Intentions
Not all wingmen and wingwomen use their powers for good. Some can be downright cruel. Sarah Michelle Gellar nailed her role as the evil wingwoman Kathryn Merteuil. Sure, she’ll fix someone up and play the socialite cupid, but only if she gets something out of it. Kathryn is basically an evil version of Cher from Clueless. Cruel Intentions is based on a French novel from the 1700s, so maybe the French do the whole wingman thing a little differently.
Lili Taylor in Say Anything…
Lloyd Dobler (John Cusack) broke a lot of hearts when he hoisted that boombox above his head and played “In Your Eyes” to win over Diane Court (Ione Skye). Lloyd never would have gotten there if it weren’t for the help of his wingwoman, Corey Flood (Taylor). Corey is best known for her endless stream of break-up songs about her boyfriend, Joe (Loren Dean). While she has her own relationship problems, Corey’s help and advice make a solid case that all men would be better off with a female as their wing.
Jerry Levine in Teen Wolf
It takes a special sort of person to be the wingman to a basketball-playing werewolf. Stiles, played by Levine, is just the guy for the job. He manages to be an over-the-top character in a movie about werewolf Scott Howard (Michael J. Fox) playing basketball like Michael Jordan. With his love for urban surfing, flare for offensive T-shirt slogans, and ability to turn boring high school keggers into performance art, Stiles is the ultimate ’80s movie slacker. He ups his wingman credentials by encouraging his friend to take his wolf-man skills to the court, and then helping him steer between the classic ’80s movie dual love interest: the hot popular girl and the bookish girl next door. Guess which one wins in the end?
Kelly LeBrock in Weird Science
If you could scientifically design and engineer your perfect wingwoman, it would be Lisa (LeBrock). We know this because that’s exactly what happens in Weird Science. Nerds Gary Wallace (Anthony Michael Hall) and Wyatt Donnelly (Ilan Mitchell-Smith) play Dr. Frankenstein, and the end result is Lisa, the woman of their dreams. Lisa will do anything that the boys desire. Being nerdy teenagers, all they desire is girlfriends. Lisa becomes a super-powered dating coach, teaching her protégés how to be confident and stand up for themselves. This only starts to lose its believability when you ask why neither kid just dated Lisa herself.
Thomas Haden Church in Sideways
Thomas Haden Church’s character, Jack, would be an ideal wingman for almost anyone but the pent-up and uptight Miles (Paul Giamatti). Where Jack is trying to get his recently divorced friend to loosen up, Miles just wants a quiet vacation of golf and wine with a close friend. But quiet vacations don’t make for good movies. Jack is a wingman with hidden intentions, looking for one last time out on the prowl before his wedding, and Miles is dragged along for the ride. It turns out that lying, cheating, broken noses, fake car crashes, and no Merlot were exactly what Miles needed to get him out of his funk. Sometimes a wingman’s methods will be unconventional, but it can still work out in the end.