Best Vince Vaughn Movies List: Top 5 of All Time

Vince Vaughn is arguably the funniest actor currently in Hollywood. The list of Vince Vaughn movies include some of the most funny movies of all time. While known mostly as a comedy actor today, his career breakthrough was in the 1996 popular indie film, Swingers, and his acclaim grew after he starred in the 1998 remake of one of the best horror movies ever, Psycho.

Trying to figure which of his memorable and often funny films is the best is difficult. But, this list of Vince Vaughn movies is focused on the Top 5 movies with Vince Vaughn of all time, beginning in the mid-1990s when he first appeared prominently on screen, through his most recent film roles.

For the purposes of this top 5 list of Vince Vaughn movies, the movie must have been entertaining, well-received commercially and/or critically, perhaps epic in nature with a lasting impact, iconic in its time, and Vaughn must have been a significant player in the film.

Best Vince Vaughn Movies List of All Time

5. Old School (2003) – This position on the top Vince Vaughn movies list might not please anyone. Some might prefer his classic role in Swingers, but that film was not included because it was knocked down a bit as more of an ensemble cast. Others probably think this should be higher on the list, but Vaughn’s role was just one of the many strong comedic roles in the film. Many would consider this more one of the best Will Ferrell movies.

4. Psycho (1998) - You may not have known of Vince Vaughn after the indie movie Swingers made it big, since there were other popular actors to come out of that film. However, most remember his memorable appearance as the lead in this very frightening retelling of the class horror flick.

3. Dodgeball: A True Underdog Story (2004) – It may not be movie making at its finest, but Dodgeball is one of those comedy movies that you can’t help but watch over and over again. It is also the most Vaughn-led of the best Vince Vaughn movies. The film features an interesting love triangle in which Vaughn lures away the female lead (Christine Taylor) from her real life husband, Ben Stiller’s character.

2. The Break-Up (2006) – Also one of the best Jennifer Aniston movies, this memorable romantic comedy doesn’t follow the traditional “happy ending” plot flow. It does offer lots of funny moments as the joy of young love turns into a bitter relationship between two roommates. Vaughn is brilliant and without his subtle humor, it would not be nearly as entertaining.

1. Wedding Crashers (2005) – Not only one of the best Vince Vaughn movies, Vaughn and Owen Wilson combine to form one of the best comedy duos in recent memory. The pair sets out on a funny and entertaining journey through the wedding circuit without a care. Once they find the potential for real relationships, things get very interesting. The supporting cast in this film is amazing, especially the hugely talented Isla Fisher.

No doubt there are great Vince Vaughn movies not included in this list and likely more good ones to come. In fact, there are several that could have been comfortably included without reservation. However, the list in place gives a good scope of the legacy of Vince Vaughn films that now spans about 15 years.

Want to tell us your favorite film not on our list of Vince Vaughn movies and why? Just add a comment and share your thoughts!

This feature article about the Best Movies with Vince Vaughn was written by Neil of Movie Room Reviews

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