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.