Top 10 Vince Vaughn Movie Moments (Video Edition)

Last Updated on August 3, 2021

Vince Vaughn has pioneered a very distinct type of character in the last 20 years of his career: the lovable douche. After several years of playing varied dramatic and indie roles, Vaughn settled in nicely in the late 90s as that asshole character that still got the girls, a mentor and idol for guys everywhere. With his latest collaboration with Owen Wilson, THE INTERNSHIP, opening today, here is a look back at Vince’s ten best movie moments. The movies themselves may not always be that great, but when it comes to Vince Vaughn you know there will be at least one classic asshole moment for us to love. If your favorite didn’t make the cut, be sure to add it in the talk back below!


THE INTERNSHIP is going to be hard pressed to match the magic that Owen Wilson and Vince Vaughn made with WEDDING CRASHERS. Vaughn steals the movie dealing with the crazy Isla Fisher. I could have gone with the “Make me a bicycle, clown!” scene, but I think Vaughn’s revelation to the late great Henry Gibson ranks as one of the best movie rants of all time and definitely the highlight of Vaughn’s career to date.


Another supporting role for Vince Vaughn that turns out to be right in his wheelhouse. I honestly could have seen Vaughn, Will Ferrell, and Luke Wilson trade parts and film this movie three different ways and I think it would have worked every time. OLD SCHOOL makes me laugh more each time I see it and the above scene gave us the phrase “earmuffs” which I still see parents use to this day.


The world would not have Vince Vaughn if not for SWINGERS and for good reason. SWINGERS gave us our first team-up of Vaughn and Jon Favreau, the debut of director Doug Liman, and the catapult that sent Vaughn on to make THE LOST WORLD with Steven Spielberg and the rest is history. Vaughn graced the posters and DVD covers for SWINGERS because his performance as Trent Walker led to dozens of quotes and a performance he has yet to rival. Douchey but lovable all started with SWINGERS. Money, baby!


A small part but one that launched the great line “Dorothy Mantooth is a saint!”. As the competing news anchor Wes Mantooth, Vaughn brought everything to his few scenes, giving ANCHORMAN yet another phenomenal cameo. I just hope Wes Mantooth appears in ANCHORMAN 2 and maybe even an appearance from his mother, Dorothy.


DODGEBALL is actually more of an anomaly when it comes to Vince Vaughn roles. Peter La Fleur is the most grounded character in the entire cast of kooky performances. Vaughn seems to cotton to the part of being the straight man and letting everyone else deliver the over the top dialogue. But, that doesn’t mean that he doesn’t get some pretty great moments like the one above where he explains how mediocrity is his preferred lifestyle. Words to live by.


Released the same year as PSYCHO and RETURN TO PARADISE, CLAY PIGEONS is one of the last dark roles that Vaughn played and by far the most fun. Here he plays serial killer Lester Long who befriends Joaquin Phoenix’s character and takes him on one hell of a ride. This scene in particular highlights Vaughn’s recognizable chuckle and takes his Norman Bates role to another level. More fun than PSYCHO, CLAY PIGEONS is definitely an under the radar favorite and a great Vince Vaughn role.


Like COUPLE’S RETREAT, THE BREAK-UP is a mediocre movie that could have been so much better. The exes getting revenge on each other was played up in the trailer as the crux of the movie which actually turned out to be a downer of a story. Vaughn co-wrote the screenplay which plays like a love letter to his hometown of Chicago. As someone who calls the Chicago area home and is a big Cubs fan, this scene is my favorite of in the movie. Cubs fans will truly understand this moment better than anyone else.

#8 – MADE

When it came time for his directorial debut, Vaughn’s buddy Jon Favreau cast his friend in what is often looked at as an unofficial follow-up to SWINGERS. MADE could not be further from SWINGERS but still retains an indie feel to it. MADE is very funny and having Favreau once again play straight man to Vaughn’s immature character is an enjoyable way to spend a couple of hours. This scene with the two stars at a pottery store is my favorite in the film.


Vaughn took his Masters in Douche-ology and applied it to portraying a bad guy. Having him as the antagonist makes it easier for him to just be an asshole without having to worry about any redeeming qualities for the audience. This scene gives Vaughn the chance to interact with both Ben Stiller and Owen Wilson while also sporting one of the best mustaches of all time.


It was around the release of COUPLE’S RETREAT that Vaughn completely lost me as a fan. After FRED CLAUS and FOUR CHRISTMASES, I just assumed he had quit on us and pulled an Adam Sandler. But, COUPLE’S RETREAT does have some redeeming moments highlighted by this sequence where he professes “not to panic”. Classic Vaughn.

Honorable Mention – PSYCHO

Yes, PSYCHO may be the most misguided attempt at a remake in the history of film, but it is definitely an interesting failure. Casting Vince Vaughn in the Anthony Perkins role didn’t seem special at the time, but in hindsight it is a very intriguing choice based on where his career led. Vaughn plays Norman Bates as a mildly disturbed young man with that trademark giggle. This role does make me wonder what happened to Vince’s dramatic career as I think he definitely a talented guy who hasn’t stretched himself in quite a while.


About the Author

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Alex Maidy has been a editor, columnist, and critic since 2012. A Rotten Tomatoes-approved critic and a member of Chicago Indie Critics, Alex has been's primary TV critic and ran columns including Top Ten and The UnPopular Opinion. When not riling up fans with his hot takes, Alex is an avid reader and aspiring novelist.