Holland was a founding member of the British pop band Squeeze, formed in March 1974, in which he played keyboards until 1981 and helped the band to achieve millions of record sales, before pursuing his solo career.

Holland began his career as a session musician; his first studio session was with Wayne County & the Electric Chairs in 1976 on their track “Fuck Off”.

Holland began issuing solo records in 1978, his first EP being Boogie Woogie ’78. He continued his solo career through the early 1980s, releasing an album and several singles between 1981 and 1984. He branched out into TV, co-presenting the Newcastle-based TV music show The Tube with Paula Yates. Holland used the phrase, “be there, or be an ungroovey fucker” in one early evening TV trailer for the show, live across two channels, causing him to be suspended from the show for six weeks. He referred to this in his sitcom The Groovy Fellers with Rowland Rivron. Holland also appeared as a guest host on MTV.

In 1983 Holland played an extended piano solo on The The’s re-recording of “Uncertain Smile” for the album Soul Mining. In 1985, Squeeze (which had continued in Holland’s absence through to 1982) unexpectedly regrouped including Holland as their keyboard player. Holland remained in the band until 1990, at which point he again departed to resume his solo career as a musician and a TV host.

In 1987, Holland formed the Jools Holland Big Band, which consisted of himself and for the show Gilson Lavis from Squeeze. This gradually became the 18-piece Jools Holland’s Rhythm and Blues Orchestra. The Orchestra includes singers Louise Marshall and Ruby Turner and his younger brother, singer-songwriter and keyboard player, Christopher Holland.

A fan of the 1960s TV series The Prisoner, in 1987 Holland demonstrated his love of the series and starred in a spoof documentary, The Laughing Prisoner, with Stephen Fry, Terence Alexander and Hugh Laurie. Much of it was shot on location in Portmeirion, with archive footage of Patrick McGoohan, and featuring musical numbers from Siouxsie and the Banshees, Magnum and XTC. Holland performed a number towards the end of the programme.

Between 1988 and 1990 he performed and co-hosted along with David Sanborn during the two seasons of the music performance programme Sunday Night on NBC late-night television. Since 1992 he has presented the music programme Later… with Jools Holland, plus an annual New Year’s Eve Hootenanny.

In 1996, Holland signed a recording contract with Warner Bros. Records, and his records are now marketed through Rhino Records.

Holland was an interviewer for The Beatles Anthology TV project, and appeared in the 1997 film Spiceworld as a musical director.

On 29 November 2002, Holland was in the ensemble of musicians who performed at the Concert for George, which celebrated the music of George Harrison. In January 2005 Holland and his band performed with Eric Clapton as the headline act of the Tsunami Relief Cardiff.

He received an OBE in 2003 in the Queen’s Birthday Honours list, for services to the British music industry as a television presenter and musician. In September 2006, Holland was appointed a Deputy Lieutenant for Kent. Holland was appointed an honorary fellow of Canterbury Christ Church University at a ceremony held at Canterbury Cathedral on 30 January 2009. On 1 February 2011 he was appointed honorary colonel of 101 (City of London) Engineer Regiment.

On 29 August 2005, Holland married Christabel McEwen, his girlfriend of 15 years and daughter of artist Rory McEwen. Holland lives in the Westcombe Park area of Blackheath in SouthEast London, where he had his studio, Helicon Mountain, built to his design and inspired by Portmeirion, the setting for the 1960s TV series The Prisoner. He also owns a manor house near medieval Cooling Castle in Kent.

In June 2006 Holland performed in Southend for HIV/AIDS charity Mildmay, and in early 2007 he performed at Wells and Rochester Cathedrals to raise money for maintaining cathedral buildings. He is also patron of Drake Music.

His 2007 autobiography, Barefaced Lies and Boogie Woogie Boasts, was BBC Radio 4 “Book of the Week” in the week beginning 8 October 2007 and was read by Holland.

In 2009, Holland commissioned TV series Bangla Bangers (Chop Shop) to create a replica of the Rover JET1 for personal use. Holland has previously owned cats.

He appeared on the cover of Railway Modeller magazine in January 2019. In the attic of his house, Holland has spent ten years building a 100-foot (30 m) model railway. It is full of miniature buildings and landscapes that stretch from Berlin to London. He started with photographs and paintings from early 1960s London. “In the evenings, he builds some trains and buildings before switching on some music, pouring a glass of wine and switching on the trains to watch them move around the room.”