He has appeared in Grease 2 (1982), Electric Dreams (1984), The Boys Next Door (1985), The Supernaturals (1986), Sundown: The Vampire in Retreat (1989), Waxwork 2 (1992), Gettysburg (1993), Empire Records (1995), The Real Blonde (1997), The Man Who Knew Too Little (1997), and in A Prince for Christmas (2015).

[7] He made his Los Angeles debut in Hitting Town (1980) and appeared in The Elephant Man (1980) that same year, during which he met his future wife, actress Juliet Mills.

[9] He made his debut Off-Broadway in 1981 as the title character, a homicidal drifter, in Joe Orton's Entertaining Mr. Sloane (alongside Joseph Maher and Barbara Bryne).

[13] On 14 April 2024, Caulfield appeared in the 10th Anniversary Concert of Cool Rider (the Greasiest Sequel) at the London Palladium, this time assuming the role of Mr Stuart and taking on the song "Reproduction".

Caulfield has appeared on Dynasty (1985–1986), The Colbys (1985–1987), Murder, She Wrote (1988–1991), Beverly Hills, 90210 (1990), The Rockford Files: Godfather Knows Best (1996), Spider-Man (1995–1998), Casualty (2003–2004), Emmerdale (2009–2010) and NCIS (2013).

He guest-starred on Modern Family (Season 4, Episode 16, "Bad Hair Day") playing Claire's ex-boyfriend and college professor.