Cereghino was born in Milwaukie, Oregon, on April 24, 1979, where his family has run a farm since 1908. His father, Robert "Bobby" Cereghino, was a farmer and a home builder, and his mother Nancy is an elementary and special ed teacher. Early on he was interested in US history, garnering the attention of the state newspaper, which came and interviewed him as a youngster when he continued to come to school dressed as United States Presidents. This led to him successfully running for class president and then school president. He graduated from high school as a multi-sport athlete, playing football and baseball, wrestling, and setting a school record in the mile run while running track and cross country. After graduation, he briefly lived in Nashville to start a singing career before moving to Los Angeles in 2000. His first movie role was in the 1995 film Mr. Holland's Opus, where he was included in the graduation scene because he had the proper shoes on for the period piece. His high school football experience would later aid him in his performance as one of the stunt doubles doing tackles in The Longest Yard.