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Cullum was born at Rochford Hospital in Essex. His mother, Yvonne, is a secretary of Anglo-Burmese origin, whose family settled in Wales after Burma's independence; his father, John Cullum, worked in finance. His paternal grandfather was a British Army officer, while his paternal grandmother was a Jewish refugee from Prussia who sang in Berlin nightclubs; Cullum sees her as his "cultural icon". He was raised in Hullavington, Wiltshire but currently lives in North West London.
Cullum released his first album, Jamie Cullum Trio—Heard it All Before, in 1999. A mere 500 copies were made. Original copies have sold for as much as £600 (and above) on eBay. The success of Heard It All Before resulted in Jamie being invited to appear on Geoff Gascoyne's album Songs of the Summer. After graduating from the University of Reading in 2001 (with a 1st), Cullum - who is completely self-taught, bar a few piano lessons as a youngster - released a best-selling album, Pointless Nostalgic, which stirred interest from Michael Parkinson and Melvyn Bragg. Following that, in April 2003 he signed a contract with Universal, for three albums, who beat Sony in a bidding war.