From 2003 onwards, Shepard became known from his work in the improv Candid Camera-type show, Punk'd, with Ashton Kutcher. When the show had its 2012 revival, he continued to appear. Shepard said he auditioned for Punk'd and while doing the pilot became friendly with Kutcher, who arranged for him to get an agent. He had auditioned unsuccessfully for 10 years before landing the role in Punk'd, his first.
