1. Dr. Watson, the Sherlock Holmes stories
Yes, Sherlock Holmes is undoubtedly a genius. An expert chemist with an uncanny eye for detail, he's solved countless cases by divining secrets from the sort of clutter the rest of us just edit out of a room when we walk into it. But genius or not, people like Holmes are so stuck in their own heads, they also tend to get hopelessly lost if they try and take public transportation by themselves. Fit, dour, with a pragmatic intelligence, Watson is the essential grounding force Holmes needs. He always remembers to bring along the train schedule, he's the only one who can snap the detective out of his post-case-cracking opium binges, and he knows how to joke with the clients so they’re laughing when he slips them their bill.
2. Nick Carraway, The Great Gatsby
Maybe you're calling Nick's wingman status into question because his loyalty seems questionable. He has those intimate chitchats with his cousin Daisy, but then goes gallivanting around NYC with her husband, Tom, who apparently only takes Nick along so he can finally show off his mistress to someone who hasn’t met her yet. Well, give Nick a break. You can't expect a good ole' Midwestern boy to adapt to life with this polo-before-lunch, ponies-before-dinner, jazz-bands-before-passing-out set without getting his hands a little dirty. So why is he a great wingman? He enables or covers up pretty much every romantic encounter that occurs in the entire novel. And most importantly, he's the only party guest who’s still around in the morning to help clean up the mess everyone else made the night before.
3. Mr. Hyde, The Strange Case of Dr. Jekyll and Mr. Hyde
As the story goes, Dr J starts taking a potion in order to be less repressed and boring. Or at least, to draw-out his desire for uncouth behavior (which, if you're Victorian, pretty much means most kinds of behavior) and deposit it into a vessel of unchecked primal drives, which is then given the totally discrete name “Mr. Hyde.” Unfortunately, though, all the "fun" stuff Jekyll's been dying to try includes petty theft, harassing women, and murdering elderly politicians. Soon Scotland Yard is on the trail and Hyde seems to be muscling Jekyll of his own body. Well, so maybe Mr. Hyde's not a great wingman after all. But you have to admit...he gets out of the dreary old laboratory and mixes things up! The only thing Dr. Jekyll ever managed to mix up on his own was the potion that turned him into Hyde.
4. Prince Stepan Arkadyevitch "Stiva" Oblonsky, Anna Karenina
As his festive nickname suggests, Stiva fits the wingman mold perfectly. He's the buddy who's always going overboard, always scheming, always inconveniencing people without realizing it, but who's so charming you've already forgiven him by the time he asks if he can borrow five bucks (again). He's the force of fun and philandering that brings all the other characters in the novel together. Stepan introduces his sister Anna to her beau, Count Vronsky, and it's at his dinner party that Konstantin Levin finally woos Kitty, who he's loved for years. Most crucially, he's always there to cheer up Levin whenever the latter becomes troubled by yet another disconcertingly un-fun crisis of conscience or introspection. "Come on and stop sighing over everything, Konstantin Dmitrich! Let's order some oysters and pick up chicks!"
5. Telemachus, The Odyssey
From Telemachus' point of view, the whole story of The Odyssey can be seen as an enormous build up to his chance to prove himself an epic wingman. Even while suffering insults, threats and humiliation at the hands of the suitors—men who have spent the last few decades eating his food, lounging in his house, and hitting on his mom—Telemachus maintains faith that his father will one day return home. Together he and his pop mop the floor with the suitors, and afterward Telemachus bails in a timely fashion before he has to see his parents kiss. Then there's that awkward moment when Penelope asks what Odysseus has been up to all these years...
Did we miss any?