Reynolds' career began in 1991, when he starred as Billy Simpson in the Canadian-produced teen soap opera Hillside, distributed in the United States by Nickelodeon as Fifteen. Between 1993 and 1994, he had a recurring role in The Odyssey as Macro. In 1996, he had a supporting role as Jay "Boom" DeBoom in "Syzygy", the thirteenth episode of the third season of the X-Files, and co-starred with Melissa Joan Hart in the TV movie Sabrina the Teenage Witch. In 1996 Reynolds played Bobby Rupp, boyfriend of murdered teen Nancy Clutter, in a two-part miniseries In Cold Blood, an adaptation of Truman Capote's nonfiction novel of the same name. He also appeared in the anthology The Outer Limits episode "Origin of the Species" which originally aired on November 14, 1998. Beginning in 1998, Reynolds starred in Two Guys, A Girl and a Pizza Place, playing medical student Michael "Berg" Bergen, throughout the show's four season run. He starred in the National Lampoon movie Van Wilder in 2002 and appeared in The In-Laws, with Michael Douglas and Albert Brooks, and in the Canadian production Foolproof in 2003.