Born in Milford, MI, Shepard had a routinely uneventful life until his junior year at Walled Lake Central High School, when he read a copy of Jack Kerouac's On The Road, which prompted him to ditch his college plans and roadtrip with a friend in a beat-up Mustang for the next five months. But he soon learned the value of a college education, and eventually attended the University of California at Los Angeles, where he earned his degree in anthropology, even though he had always had his sights set on becoming an actor. Displaying a knack for comedy, Shepard joined the renowned Groundlings Theater, which led to landing 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.Meanwhile, 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" (1998), which he followed with his breakout role as Ashton Kutcher's field agent for the first season of the popular hidden camera show, "Punk'd," which attempted to trap various celebrities in practical jokes. A series of smaller roles on television and in film soon followed. Shepard appeared on "Life with Bonnie" (ABC, 2002-04), playing a young commercial director who desires something other than Bonnie's wholesome image to sell her favorite childhood soup in one episode, and a plastic surgeon who leaves his mark on Bonnie's face before she goes on air in another.Continuing his track on the small screen, Shepard provided his voice for "King of the Hill" (FOX, 1996-2009), which he followed with a small role on the big screen in "Cheaper By the Dozen" (2003), a remake of the 1950s Clifton Webb family comedy. He next appeared in the Nick Lachey music video "Shut Up," which led to a subsequent appearance on the short-lived "Making the Video" (MTV, 2000-02). Shepard had his first starring role in "Without a Paddle" (2004), a buddy comedy co-starring Seth Green and Matthew Lillard about three misfit friends who embark on a childhood dream of finding a legendary bank robber's secret stash of $200,000. Instead they find trouble in the form of wild rapids, vicious Rottweilers and disgruntled deep-woods marijuana farmers. Somewhat satirizing John Boorman's classic "Deliverance" (1972), the movie found Shepard working alongside that film's star, his childhood idol Burt Reynolds.Shepard's star continued to rise when he signed on to appear in "Zathura" (2005), the sequel to the surprisingly successful "Jumanji" (1995). He next played the knuckleheaded lawyer of a man (Luke Wilson) whose participation in a scientific experiment transports him to the year 2505, where he becomes the world's smartest man in Mike Judge's "Idiocracy" (2006). In the raunchy prison comedy, "Let's Go to Prison" (2006), he played a three-time convict who opts for a fourth go-round on the inside in order to exact revenge against the son of a judge (Will Arnett). Following a small role in the sports parody "The Comebacks" (2007), Shepard earned a degree of off-screen notoriety when, not long after beginning to date actress Kate Hudson, her ex-boyfriend Owen Wilson attempted suicide around the same time pictures of Shepard and Hudson kissing were splashed across tabloid covers. While Wilson never publically commented as to the reasons for such desperation, the press deemed him lovesick over his ex moving on with Shepard. Not long after the fracas, the newly minted couple broke up. Shepard went on to appear in a small role in the Tina Fey-Amy Poehler comedy, "Baby Mama" (2008) and was a narcissistic male model in the romantic comedy, "When in Rome" (2010), which starred his future finance, Kristen Bell. Turning back to television, he landed as a regular on the small screen version of "Parenthood" (NBC, 2010-15), an ensemble comedy-drama that was adapted from Ron Howard's 1989 feature film.