Medlin began his career appearing in local and Spanish-market ads for which he achieved some acclaim. After numerous television guest appearances and small film roles, he landed a recurring role in the UPN sitcom Rock Me Baby (2003–04), appearing in 10 episodes of that program's single-season run. He was a main cast member of the short-lived Fox sitcom Happy Hour in 2006. In 2011, he began a recurring role as Judge Owen French on the Lifetime legal drama/fantasy series Drop Dead Diva, and became a main cast member for that show's fourth season (2012).