Caulfield was born in 1936 in London. He was among the generation of artists who epitomised British Pop Art, though his work often has an introspective and melancholic mood quite unlike the more upbeat style typically associated with Pop. From the 1960s until his death in 2005 he produced pictures of interiors suggesting the banality of everyday existence.

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Caulfield studied at Chelsea School of Art and then at the Royal College of Art, returning to the former to teach until 1971. His first solo exhibition was held in 1965 at the Robert Fraser Gallery, establishing his reputation. He soon held major shows in the UK and overseas. Caulfield was elected to the Royal Academy in 1993, awarded a CBE in 1996, and later received an Honorary Fellowship of the London Institute.