This former Division III college football star graduated from the Ultimate University wrestling school to become the only 10-time WWE champion in history. All the while releasing a rap album (You Can’t See Me) which debuted at number 15 on the U.S. Billboard 200 chart! While his acting career has seen medium success starring in films such as The Marine and 12 Rounds. he graduated into more macho roles in such shows as Hannah Montana and the “Pajama Party” episode of True Jackson VP. However, this picture, taken in 1995 during his senior year at Cushing Academy in Ashburnham, Massachusetts, suggests he could’ve had quite a career as a Matt Damon look-alike.