Caulfield has appeared on Dynasty (1985–86), The Colbys (1985–87), Murder, She Wrote (1988–91), Beverly Hills, 90210 (1990), The Rockford Files (1996), Spider-Man (1995–98), Casualty (2003–04), Emmerdale (2009-10), and NCIS (2013). He guest starred in Modern Family (Season 4, episode 16 - Bad Hair Day) playing Claire's ex-boyfriend and college professor, among other television programs.He played a king in Prince for Christmas on ion TV (2017).