Guide to Appreciating Vince Vaughn Movies

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Vince Vaughn is one of those actors you either really hate or really love. There is no middle ground there. His peculiar deadpan acting and often overconfident onscreen characters aren’t everyone’s cup of tea. It often takes some getting used to. In fact, some believe that the key to liking Vince Vaughn movies lies actually in the right order of watching. Before you can enjoy his movies, you need to get to know the actor and what he’s all about, and this guide is here to help you. Take a look at our selection of the best movies by Vince Vaughn and the right order you should watch them in.

Swingers (1996)

The first film you should start things off with is beyond any doubt the 1997 flick Swingers, directed by the now-famous Doug Liman.  The movie follows two unemployed actors in the 90s as they attend various Hollywood parties and try to find their way into movie elite. Although the film was written by and stars Brett Favreau, the real star is actually the slick Trent Walker, played by Vince Vaughn. His character is one of those people whose confidence is both quite amusing and incredibly infectious. Vince nails the role and acts as the fuel in an otherwise uneventful film. If there’s one movie that might help you change your mind about him, this is it.

Return to Paradise (1998)

Now, Return to Paradise is one of those films you probably never watched because the cast seemed quite peculiar – Anne Heche, Joaquin Phoenix, and Vince Vaughn. We can’t blame you for it. The truth is that the film isn’t all that good, though it has an intriguing premise and some worthy performances. Basically, two friends are confronted with a choice – whether they should return to Malaysia where they’ve spent a vacation more than two years ago and turn themselves in to save their third friend from the death sentence, or simply ignore it all and carry on with their lives. Here Vince plays an everyman and it’s such a solid performance that it’s quite easy to sympathize with him and justify his decisions. Some unpredictable events and actions somewhat ruin the film, but the fact remains that Vaughn did his job,

Dodgeball: A True Underdog Story (2004)

We’ve mentioned Vince Vaughn as an everyman before – well, it also works in comedies as well. Dodgeball is a silly little film full of slapstick comedy and physical humor, but it’s Vince Vaughn’s composure in face of it all that gives the movie its charm. The plot is fairly unnecessary – in order to save their pathetic little gym from going bankrupt, a group of unfit weirdoes enters a dodgeball tournament. The cast includes the extremely funny Ben Stiller, disturbingly crazy Rip Torn, and the comparatively normal Vince Vaughn. Even if you’re not a fan of slapstick comedy, this film will help you get to know Vaughn a little more.

Vince Vaughn and Owen Wilson at Wedding Crashers premiere

Photo: Ferdaus Shamim (Getty Images)

Wedding Crashers (2005)

The next film you should see after that one is another comedy, but slightly better – Wedding Crashers. Owen Wilson and Vince Vaughn play two men whose main hobby is crashing weddings to get free food, drinks and, of course, women. Wilson and Vaughn are old friends so whatever they do on the screen seems genuine and unforced, which is one of the strongest points of this film. Instead of just usual Vaughn’s, both of these characters are slick and talkative, carrying the film and its comedy together. When you add the breath-taking Rachel McAddams to the mix, the movie becomes a truly enjoyable experience that doesn’t offer too much but also doesn’t overstay its welcome.

True Detective Season 2 (2015)

In recent years, TV shows have taken over for the movies, so you’ll forgive us in advance for this seemingly out of place entry. The first season of the True Detective propelled Matthew McConaughey to fame and revived the fairly dead career of Woody Harelson. People believed that the second season will do the same for its protagonists – Colin Farrell, Rachel McAddams, and Taylor Kitsch and, while it may have done that, it also brought forward another unlikely star – Vince Vaughn. In the show, Vaughn plays a high-class criminal who is both vicious and sympathetic at times. Somehow he managed to bring his trademark talkative, confident character and make him dangerous and awe-inspiring. What makes this performance great is the fact that even those people that utterly hate Vince Vaughn are able to enjoy hating him in this show, which only adds to his performance. His final scenes really round up the performance and allow him to seek even tougher parts in the future.

Upcoming Movies

You might think that, following his performance in True Detective, Vaughn will be swamped with work, but it doesn’t appear that way. Recently he finished shooting a minor role in Roland Joffé’s The Forgiven, as well as a slightly bigger part in S. Craig Zahler’s Brawl in Cell Block 99. Zahler is a fairly new director and seems to have taken a liking to Vaughn’s performance as he has also taken him on for his 2018 cop drama alongside Mel Gibson called Dragged Across Concrete. Whether it will be Vaughn’s true entry into the world of drama, we have yet to see but, for now, he seems to be sticking to the genre he knows. Vince Vaughn’s new movie, Fighting with My Family is apparently one of those good old comedies, but with some pro-wrestling twists and is written by Stephen Merchant, one of the geniuses behind the Office (the original one), so we have high hopes for this one.

Are you one of those people who hate or love Vince Vaughn movies? What is your favorite movie? Do you think he’ll continue towards some other serious roles?