Chuck "The Shermanator" Sherman is an acquaintance and a friend of Jim, Finch, Oz, Kevin. He also becomes a friend to Stifler, who was his rival until American Reunion.
History[]
He is obsessed with the Terminator movies and thinks that Terminator 2 is the greatest movie ever made.
In American Pie, Sherman seemed to have lost his virginity during a party at Stifler's house. However, at the end of the movie it was revealed that he lied about this fact and the girl with who he apparently "slept" with called him a liar in front of everyone during Prom night, and disclosed some embarrassing facts about him which made him wet his pants.
In American Pie 2, Sherman appears at the party where he charms and loses his virginity to Nadia, who had earlier been rejected by Jim after he realized that he was in love with Michelle and Nadia had a lust for nerds. This display was spotted by a shocked Stifler. The next morning, Sherman is in bed with Nadia cuddling him and he is pleased with his success.
In Band Camp he is shown to have returned as a guidance counselor at East Great Falls High School, having to deal with Stifler's younger brother Matt Stifler. When Matt came to him to ask for an honest opinion about Stifler's reputation in high school, Chuck explained that he was only liked for his infamous parties.
In American Reunion, he attends the reunion and revealed to Stifler that after high school he also had gotten married, had a child, but got divorced. Stifler apologizes to him for his troubles while Sherman accepts and states that at least he got to keep his son who is named Furlong (named after actor Edward Furlong, who played John Connor in Terminator 2). Stifler helps Sherman out of his funk by setting him up with Loni Lipstein, something he immediately goes for. It is unknown if a relationship started from there or if it was a one night stand.