Holland was a founding member of the highly acclaimed and successful band Squeeze. He played piano and keyboards on all their singles and albums through 1980, when he left the band to concentrate on his own career (though he would later return).

Holland had actually begun issuing solo records as early as 1978 (with an EP called Boogie Woogie '78), and continued his solo career through the early 1980s, releasing an album and several singles between 1981 and 1984. He perhaps gained more fame, however, as a TV host, co-presenting the Newcastle-based TV music show The Tube with Paula Yates. Holland achieved notoriety by swearing to camera on live TV causing the show to be lifted for 3 performances, and was fired as a result.

In 1985, Squeeze (which had continued in Holland's absence through 1982) unexpectedly re-grouped. Holland was once again the keyboard player for the band through 1990. At that point, he again departed Squeeze on amicable terms to resume his solo career as both a musician and a TV host.

Since 1992 he has presented the eclectic music programme Later with Jools Holland, plus an annual New Year's Eve "Hootenanny", and has shaken off his "bad boy" image to become a respected musician.

Singers Sam Brown and Ruby Turner often join his touring band, The Rhythm And Blues Orchestra.

Holland is a big fan of the cult 1960s tv series "The Prisoner" owning some of the costumes and props from the series and occasionally appears wearing the trademark brown-with-white-pipe blazer featured in the series. Holland lives in the Westcombe Park area of Blackheath in south-east London, where he has had his studio built to his own design, loosely inspired by Portmeirion the setting for "The Prisoner".

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. He is also a published author and appears regularly on television shows besides his own and contributes to radio shows. In 2004, he collaborated with Tom Jones on an album of traditional R&B music. In January 2005 Jools and his band performed with Eric Clapton as the headline act of the Tsunami relief concert in Cardiff's Millennium Stadium.

On 29 August 2005 Holland married his partner of fifteen years, Christabel McEwen. The wedding at St James's Church, in Cooling near Rochester, was attended by stars including Ringo Starr, Robbie Coltrane, Stephen Fry and Dawn French.

Other guests included comedian Lenny Henry, singer Lulu, actress Jennifer Saunders and her husband Adrian Edmondson.