10. Grandma’s Boy
Hill co-starred in this 2006 stoner comedy, which was a Happy Madison film, alongside Allen Covert, Nick Swardson, and Kevin Nealon. People may not have realized who Hill was at the time since he this was one of his first films, but he’s immediately recognized when watched now. The movie is about a 36-year-old video game tester, Alex, who is forced to move in with his Grandma and her two crazy friends. Hill plays one of Alex’s co-workers, Barry, who is also a video game tester.
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