Shaker Heights, Ohio, in 1957. Roger Ailes, who became the CEO of Fox News, was a childhood acquaintance of Pendleton in Warren, Ohio. Ailes took acting classes taught by Pendleton's mother.

Pendleton became interested in the theater through his mother, whose performances he watched when he was young. In junior high school, he put on his own performances in the basement of the family home. He participated in theater while attending Yale University,