The Best Wingmen In Movie History

The wingman is a very specific type of friend. He doesn’t necessarily have to be your best friend, but he often is. And the role is expected of you as well. Sometimes you’re the pilot, and sometimes you back him up. Wingmen are responsible for many things in a man’s life: helping you with women, getting into fights they have no personal stake in, sometimes letting you know when you’re fucking up. In an odd, non-homoerotic way, your wingman is your wife before you meet your actual wife. He might even introduce you to your wife. Hell, he could very well sleep with her first, just so the two of you can meet awkwardly in the kitchen the next morning. Movies are particularly great at portraying the complex relationship between a protagonist and his wingman.

1. Trent Walker

Screen Shot 2014-04-15 at 9.34.55 AM

Trent has all the qualities you want in a best friend. He’s outgoing so you don’t have to be, he goes to bat for you, and he’s sometimes an asshole. Being an asshole is an underrated quality in a friend. We all get into weird, depressed states, or just make terrible life choices, and we often need a friend who’s going to be a dick to us more than we need a sympathetic ear. A wingman is not just someone who will help you pick up women. He is someone who will force you to get to a place where you’re actually attractive to them.

2. Chewbacca


Have you ever wished your dog was actually a person? Sometimes it’s like he’s the only creature in the world who gets you. Well, that’s Chewie. He’s fiercely loyal, he can kill motherfuckers with sheer physical force, and he can drive your badass spaceship so you can take a break to hit on the princess. Plus, Han is the only person in the galaxy who can understand him (okay sure, so can Yoda, but he’s a hermit at this point in the story). Isn’t it awesome when you and your best wingman have such a great shorthand that you can talk in front of people and your words are completely incomprehensible to them? Chewbacca is just pure awesome. He doesn’t take shit from anyone, and he’s often the first person to warn Han when trouble is coming. The fact that he was the prototype for one of John Candy’s greatest comedic movie roles a decade later is just a bonus.

3. Raymond Babbitt


Raymond, also known as “Rain Man,” is not your prototypical wingman. He’s not totally aware of everything that’s going on, and it’s often very taxing for late ‘80s Tom Cruise to take care of him. But he also does something for Charlie that every good wingman should do. He challenges him, and ultimately brings out the best in him. Charlie realizes late in the film that Raymond is actually the older brother and the protector figure from his childhood that he had always assumed was a figment of his imagination. That’s another thing wingmen do for you. They protect you even when you don’t realize or don’t remember it. It also doesn’t hurt that Raymond is also a killer in Vegas.

4. Tyler Durden


This might seem a bit out of left field since SPOILER ALERT (but who gives a shit, this movie is almost 20 years old) Tyler Durden and Edward Norton’s unnamed narrator are the same person. That’s right, sometimes you are your best wingman. It’s easy for all of us to slip into the khakis and fancy apartment traps in life, and often, the only person with the knowledge of our weaknesses that can kick our asses is us. Ed knows he’s not happy, but he doesn’t know why until his subconscious manifests itself into a delusion and literally kicks his ass. Sure, Tyler turns out to be the crazy, psychopathic side of him, but the point still stands.

5. Ferris Bueller


I’ve probably mentioned this in a piece before, but if you didn’t already know, Ferris Bueller is not the protagonist of Ferris Bueller’s Day Off. Cameron is. Cameron is the character who actually has an arc in the story. Ferris doesn’t change or learn anything over the course of the movie. He begins and ends as a charismatic engine of entertaining mischief. Cameron, on the other hand, learns to lighten up and also to stand up to his overbearing father by the end. In fact, there are some who believe that Ferris Bueller actually only exists in Cameron’s imagination (hence why I placed him directly after Tyler Durden). I don’t personally subscribe to that notion, but I’m never against anyone coming up with an overly complex explanation for why a movie tells the story that it does. The point is, Ferris brought about the change that Cameron needed. And that’s a true wingman, even if he does steal the show sometimes.


Calm down, outraged Internet reader. I left Maverick’s literal wingman, Nick “Goose” Bradshaw, off intentionally. I’m of the belief that if someone completely encapsulates perfection of a certain art form, he or she should be left off the conversational list. That’s why any time I talk to people about my favorite guitarists, I just leave off Hendrix because he’s the undisputed best–don’t come at me with that weak ass Clapton or B.B. King bullshit. It’s the same with basketball. MJ is the GOAT. We know that, so let’s not waste time by listing the reasons why. Goose is the reason why we use “wingman” as a colloquial term in the first place. So no, my hasty conclusion-reaching reader, I didn’t forget Goose.

Email this to a friend

Randall J. Knox

Randall J. Knox (known colloquially to his friends as "Knox") left his native Texas a few years ago, and moved to Los Angeles in his '03 Buick Regal named LeRoi to write movies with his jackass college buddies. His favorite things in life include bourbon that's above his pay grade, mix CDs, and Kevin Costner films. He isn't sure what "dad jeans" are exactly, but he knows he wants a pair.

8 Comments You must log in to comment, or create an account
Show Comments

For More Photos and Content

Latest podcasts

Download Our App

Take PGP with you. Get

New Stories

Load More