His mother, Yvonne, is a Burmese secretary whose family settled in Wales after Burma's de-colonization; his father, John Cullum, worked in finance. His paternal grandfather was a British Army officer, while his paternal grandmother, Omi, was a Jewish refugee from Prussia who sang in Berlin nightclubs; Cullum sees her as his "cultural icon". He was raised in Hullavington, Wiltshire.
Cullum released his first album, Jamie Cullum Trio—Heard it All Before, in 1999. A mere 600 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, 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. Following that, in April 2003 he signed a contract with Universal, for three albums, who beat Sony in a bidding war for the prodigy.
Cullum then started recording his second album, Twentysomething, which was released in October 2003. It went platinum and became the #1 selling studio album by a jazz artist in the United Kingdom. Cullum's breakout hit in the United States was "All At Sea" closely followed by a reworking of Radiohead's "High and Dry".
Although primarily a jazz musician, Cullum performs in a wide range of styles and is generally regarded as a "crossover" artist with his musical roots firmly based in jazz. Cullum draws his inspiration from many different musicians, from Miles Davis to Tom Waits and many more. Cullum has been part of quite a long list of bands, ranging from banging drums in a hip-hop group to playing guitar in rock bands such as Raw Sausage and The Mystery Machine, in his teenage youth.
Together with his elder brother, Ben Cullum, he wrote the music for a West End stage version of When Harry Met Sally.
The British Jazz Awards first recognized Cullum's growing success by awarding him the "Rising Star" award, at the 2003 ceremony in July. At the 2004 Brit Awards, Cullum was nominated in the "British Breakthrough Act" category. He performed live in the ceremony at Earl's Court, a duet with Katie Melua of The Cure's "Love Cats". In the 2005 Brit Awards, Cullum was nominated for two awards: "Best Male Artist" and "Best Live Act". Following that, Cullum was nominated for a prestigious Grammy award in 2005, and went on to win yet another award at the BBC Jazz Awards, this time scooping Radio 2 "Artist Of The Year", as voted for by listeners of Radio 2.
Cullum's third major label album, entitled Catching Tales, was released on the September 26, 2005, in the United Kingdom and The Netherlands, and two weeks later in the United States, on October 11.
The American and French versions of Catching Tales do not feature Fascinating Rhythm, unlike the European version which does. The second single released, in the United Kingdom and the Netherlands, was Mind Trick, a funky track written by Jamie and his brother Ben. The third single to be released from the album is the self-penned track "Photograph". Written on New Years Day (2005) after Jamie found a box of photographs, reminding him of how special his youth was, despite the fact it didn't seem it at the time.
A special edition version of Catching Tales is also available in Europe, featuring "an exclusive 20 minute behind-the-scenes documentary following Jamie throughout recording, mixing, the video shoot and on the road across Europe. It also includes a fabulous interview. 28-page booklet contains exclusive photos, Jamie rarities, extended liner notes plus a track-by-track introduction from Jamie himself!". Catching Tales has also been released on vinyl, as well as the first single, Get Your Way.
Catching Tales was to feature a collaboration with Pharrell Williams. Cullum and Williams recorded various songs together and it was thought that a song titled 'Wifey' would make an appearance on Catching Tales. Unfortunately, due to publishing laws, it ended up being taken off the album. Usher recorded a version of the song "Wifey", which was released on a special Japanese import. There is a possibility of "Wifey", or one of the other tracks they previously recorded together, being released on Pharrell's forthcoming solo album, release date unknown.
The album Catching Tales has been produced by Stewart Levine, who also produced "Twentysomething".
Cullum has been touring with the new album, Catching Tales, since the end of October 2005 and will continue to do so until November 2006. Playing gigs in places such as: Singapore, Hong Kong, New Zealand, South America, South Africa, Brazil, Chile, Argentina, Germany, Spain, as well as returning to America no less than three times this year, to tour extensively. Cullum has played at many large music festivals, including Coachella 2005 and the 2006 South by Southwest, and will be playing the 2006 Playby Jazz Festival.
It is rumoured that Cullum will be taking the whole of 2007 off to write new music and collaborate with various musicians.
He also played the part of DJ English Hughie in the computer game, The Movies.