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Great Wingmen in Movie History

Updated on August 19, 2015


What makes a great wingman? Some would say that it's a good friend. Some would say that it's someone loyal. For the purposes of this article, we will say that a great wingman has all of the following qualities:

- Is someone who would make you look good in a social setting.

- Is someone who can run interference while you are attempting to get to know someone.

- Is someone who would have your back in a fight.

- Is someone who knows how to remain in the shadows, who knows their role in such settings.

AskMen.Com Gets It Wrong

Now, one article that is listed below has their version of the Top 10 Movie Wingmen. It was a poll done by One oversight they forgot to take into account is the wingman's duty of running interference for the friend. They had Chewbacca as their top choice. How does Chewbacca run interference when Han is the only one who can ever understand him?

Plus, sometimes running interference can mean a lot of different things. You're telling us that one of Leia's princess friends will be into Chewy? Maybe after a brazilian wax. No, I think not, as the top wingman in movie history.

Chuckie Sullivan

Chuckie Sullivan - Good Will Hunting (1997)

What makes Chuckie (Ben Affleck) a great addition to this list you ask? He fights alongside his friend, he goes to boring meetings for him and extorts the people there, and he puts some ambition into his good friend, Will Hunting.

One notable quote that sums up why Chuckie is a great addition to this list: 'Look - you're my best friend, so don't take this the wrong way. In twenty years, if you're still livin' here, comin' over to my house to watch the Patriots games, still workin' construction, I'll fuckin' kill you. That's not a threat; now, that's a fact. I'll fuckin' kill you.' (Source)

Captain Jack Sparrow - The Pirates of the Caribbean

Captain Jack is certainly not your typical wingman. While he hardly ever fades into the background, he mentors Will Turner into the type of man worthy of a woman like Elizabeth Swann.

Good with the ladies and handy in a fight, Captain Sparrow is always entertaining to be around. He's the life of the party, but someone you could trust on a deserted island with the girl of your dreams.

He also proved that he's willing to take one for the team and go down with the ship, if needed. That's what you need in an ideal wingman.


Tyler Durden - Fight Club

How is this even possible? Sometimes the best wingman is the other side of you. In this case, the multiple personality that Edward Norton's character created to do the things he was too insecure to do himself.

Want to get the girl, ok. Send in Tyler. Need to get into a fight, Tyler's always up for a fight. Makes you look good? Yup, stylish and edgy. That's Tyler.

Jeremy Grey - Wedding Crashers

How good a friend is Vince Vaughn's character you ask? He always makes sure his buddy hooks up and compliments his strengths. He refuses to leave his side during crazy family time and is willing to run interference with whichever person gets in the way (sister, brother). He even gets to punch out the ex-fiancee at the end of movie to protect the main character and help him get the girl. Solid selection here.

Goose - Top Gun

Goose was pretty good, but not quite our top wingman. The flaw comes in the interference running category. Goose's marriage to a young, and smoking hot, Meg Ryan complicates his effectiveness in that area.

No doubt he was great at making Maverick look good, especially with his backup vocals to 'You've Lost That Loving Feeling.' And he was pivotal in the fight scenes, even willing to give his own life for Maverick's needs.

The volleyball teamwork keep him in the top two, but there's one wingman that outdoes him.

Holliday-Ringo Latin Scene

Doc Holliday - Tombstone

Talk about the perfect wingman. From noticing the lightning that strikes between Wyatt Earp and Josephine Marcus, to having Kurt Russell's character's back on multiple occasions:

1. When Billy Bob Thornton's Johnny "Madcap" Tyler comes at Earp with a shotgun.

2. When a drunk Johnny Ringo wants to mix it up with Earp.

3. At the shootout at the OK Corral.

4. When he confronts Johnny Ringo in the woods and kills him for Earp.

Kilmer's Doc Holliday was both flashy and invisible when the vixen of Earp's dreams was around. He was witty and rugged, well-spoken and dangerous. And he knew what his friend wanted and had his back until he got it. That's true wingsmanship right there.

Who is the best movie wingman of all-time?

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    • Larry Rankin profile image

      Larry Rankin 2 years ago from Oklahoma

      This article was great fun. I enjoyed it thoroughly.