1. Wedding Crashers, 2005
Rotten Tomatoes Rating: 75%
This is Wilson’s most memorable film for many reasons. It was probably the biggest comedy in film at the time and Vince Vaughn had tremendous chemistry with Owen Wilson. While Wilson is hilarious throughout the whole movie, it is very impressive how his character transforms throughout the film. He starts out as a womanizer until he meets Rachel McAdams. He falls in love with her at first sight and he changes into a love struck, maturing adult.
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