As a teenager, Shepard spent years traveling with her, working racetrack events before eventually moving to Los Angeles. There, a turning point came when he was introduced to The Groundlings, a well-known improv group. It was his first real step into acting—and one that would gradually reshape his future.
From there, opportunities began to emerge. He appeared on Punk’d alongside Ashton Kutcher, gaining recognition for his comedic timing. Film roles followed, including appearances in Without a Paddle and Baby Mama.