Vince Vaughn has been working in the industry for over three decades, and it was the mid to late '90s that his career really took off. He made his feature film debut playing a supporting character in the underdog sports film Rudy. From there, he became better known in the comedy genre for his role in the 1996 movie Swingers. Vaughn then acted in a series of other comedies throughout the end of that decade and the early 2000s, including Zoolander, Old School, Starsky & Hutch, and more.