Shepard was born in January of 1975 in Milford, Michigan. His life was routinely uneventful until the eleventh grade, when Shepard read a copy of On The Road, by Jack Kerouac. Immediately, his college plans vanished, as he jumped on the road with a friend in a beat-up Mustang and spent the next five months careening down the highway into the dark American night. However, Shepard soon learned the value of needing a college education and a place to sleep that didn’t have four wheels and a V-8. After returning home from his adventures, Shepard attended UCLA where he earned a degree in anthropology.
Despite the strange choice of study, Shepard had his sights set on acting: he joined the world renowned Groundlings while still studying the significance of Olduvai Gorge. After graduating UCLA, Shepard continued with the Groundlings, which eventually led to his role on "Punk’d". In between, Shepard went on countless auditions and appeared in several commercials, including an appearance as a golfer in a lawnmower spot and a guy who nearly gets his head knocked off by Evander Holyfield in a popular beer ad. Shepard made his feature film debut in “Hairshirt” (1998), a low-budget romantic comedy that won several awards at the 2000 Slamdunk Film and Video Festival. His next feature role was in the independent and virtually unknown “Boyz-N-The-Burbs”.
A series of smaller roles on television and in film soon followed. Shepard appeared in a couple episodes of “Life With Bonnie” (ABC, 2002-2004). In the “Act Natural” episode, Shepard played a young commercial director who desires something other than Bonnie’s wholesome image to sell her favorite childhood soup. And in “Nip, Tuck and Roll”, he played Dr. Iskarr, a plastic surgeon who leaves his mark on Bonnie’s face before she goes on air. Shepard provided his voice for “King of the Hill” (FOX, 1996- ) in the “Girl You’ll Be a Giant Soon” episode, had a small role in “Cheaper By the Dozen” (2003), an remake of the 1950’s Clifton Webb family comedy and appeared in the Nick Lachey music video Shut Up, which led to a subsequent appearance on the short-lived “Making the Video” (MTV, 2000-2002).
Shepard had his first starring role in “Without A Paddle” (2004), a buddy comedy co-starring Seth Green and Matthew Lillard. Three misfit friends embark on a childhood dream of finding a legendary bank robber’s secret stash of $200,000, but instead they find trouble in the form of wild rapids, vicious Rottweilers and disgruntled deep-woods marijuana farmers. Somewhat resembling/satirizing John Boorman’s classic “Deliverance” (1972), the movie found Shepard working alongside childhood idol Burt Reynolds. Meanwhile, Shepard’s star continued to rise when he signed on to appear in “Zathura” (lensed 2004), the sequel to the surprisingly successful “Jumanji” (1995).