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Beginning 28 May 2015, he toured Australia with his wife, Juliet Mills, and sister-in-law, Hayley Mills, in the comedy Legends! by Pulitzer Prize winner James Kirkwood. He voiced James Bond in the video game James Bond 007: Nightfire (2002).

"Maxwell Caulfield is the ideal spider in the web", wrote one critic, saying he [Caulfield] was "as disarming of himself as he is of others – which gives this revival that tragic tinge of great comedy."

In 2007, he made his West End stage debut as Billy Flynn in the long-running London production of Chicago; he then resumed the role of Flynn for the Broadway production of Chicago in November 2007. Alongside Lois Robbins, Caulfield – playing the character of Julian Winston – finished up an Off-Broadway production of the comedy Cactus Flower (2011).

He made his Broadway debut in J. B. Priestley's An Inspector Calls opposite Siân Phillips. He played opposite Jessica Tandy and Elizabeth Wilson in Salonika at the Public Theater in New York City (appearing fully nude for much of the play). He appeared in Joe Orton's black comedy Loot at the Mark Taper Forum in Los Angeles. In 2006 he drew attention for 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, opposite Kate Mulgrew.

He became a naturalized United States citizen on 5 September 1991.

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.

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 as the sexy amoral homicidal titular drifter in Joe Orton's Entertaining Mr. Sloane in 1981, alongside Joseph Maher and Barbara Bryne. His performance was widely praised:

Caulfield has been married since 1980 to actress Juliet Mills, daughter of actor Sir John Mills and writer Lady Mills (née Mary Hayley Bell), and brother-in-law of Jonathan Mills and actress Hayley Mills. Caulfield is stepfather to Melissa (née Miklenda; Mills' daughter from her second marriage) and Sean Caulfield (born Sean Alquist; Mills' son from her first marriage).

Caulfield made his New York City debut in Hot Rock Hotel (1978) after moving from the UK to the United States, and the following year made his stage debut in Class Enemy (1979), in which he bagged the lead role (Players' Theatre, West Village); he won a Theatre World Award for his performance. He made his Los Angeles debut in Hitting Town (1980); and took a role in The Elephant Man (1980) the same year, which was when he met future wife Juliet Mills.

Maxwell Caulfield (né Newby; born 23 November 1959) is a British-American film, stage, and television actor and singer. 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), and The Man Who Knew Too Little (1997). He recently appeared as the King in A Prince for Christmas (2015).

Maxwell Newby was born to Peter Newby on 23 November 1959 in Belper, Derbyshire and Oriole Rosalind (née Findlater) — although he later claimed to be a native of Glasgow, reportedly to be "more interesting". By 1965, his parents had divorced. Although not a working child actor, aged around 7, he played "Ted" (under the name 'Maxwell Findlater', using his mother's maiden name) in the 1967 film, Accident. The film's screenplay was written by Harold Pinter and starred Stanley Baker, Dirk Bogarde and Michael York.