Theatre
His stage debut in London was dancing in a "nude show" to music by Led Zeppelin and Pink Floyd. Being an exotic dancer at London's Windmill Theatre led to him obtaining an Equity card, enabling him to work as an actor. After obtaining a green card, relocated from the UK to the US at age 18, making his New York City debut in a gay farce, Hot Rock Hotel (1978). The following year, in Class Enemy (1979) (which eventually went Off-Broadway), he played the lead role and won a Theatre World Award for his performance. 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.
In the early 1980s, Caulfield was an active member of the Mirror Repertory Company, part of The Mirror Theater Ltd, performing in numerous repertory productions including Paradise Lost, Rain, Inheritors and The Hasty Heart. 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). His performance was widely praised; one critic wrote:
Maxwell Caulfield is the ideal spider in the web...as disarming of himself as he is of others — which gives this revival that tragic tinge of great comedy.
Caulfield made his Broadway debut in J. B. Priestley's An Inspector Calls opposite Siân Phillips. He performed opposite Stacy Keach in Sleuth in Los Angeles in 1988. He appeared with Jessica Tandy and Elizabeth Wilson in Salonika at the Public Theater in New York, appearing fully nude for much of the play, and in Joe Orton's black comedy Loot at the Mark Taper Forum in Los Angeles. In 2006, Caulfield drew attention over his bare-chested scene in the Off-Broadway two-hander Tryst, opposite Amelia Campbell. In 2007, he performed in the Charles Busch play Our Leading Lady with Kate Mulgrew.
In 2007, Caulfield made his West End debut as Billy Flynn in the long-running London production of Chicago; he then resumed the role of Flynn for the Broadway production in November 2007. In 2011, he appeared in an Off-Broadway production of the comedy Cactus Flower.
On 14 April 2024, Caulfield appeared in the 10th Anniversary Concert of Cool Rider (the Greasiest Sequel) at the London Palladium, playing the role Mr. Stuart and performing the song "Reproduction".
