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In The Dilemma , Vince Vaughn plays a man who witnesses his best friend’s wife cheating with another man. Ron Howard’s latest film is a departure of sorts for Vaughn compared to other films if only because the overall tone cannot be described as a “laugh riot.” Still, how did Vaughn become one of the most bankable comedy stars in Hollywood after beginning his career in drama? You can always trace a direct line through a handful of important roles to illustrate what led to an actor’s current success, and with Vaughn, that line was definitely on a downward slant until Todd Phillips came along and cast him in Old School . Let’s look at eight performances — including one of his earliest — that trace the evolution of one Vincent Anthony Vaughn.

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8 Milestones in the Evolution of Vince Vaughn