Clive Gregson’s professional music career started as he took the role of lead-singer of Any Trouble, the band he had co-founded in the mid 1970s, as well the role of songwriter and rhythm guitarist after co-founder Tom Jackson left. Having recorded and released Gregson’s composition Yesterday’s Love as an indie single in 1979 Any Trouble began to receive airplay courtesy of BBC Radio 1 DJs John Peel, Andy Peebles and others in the UK. This led to interest from major record labels including WEA, Chrysalis, EMI and Stiff. They selected Stiff “because they were our kind of people”.

Any Trouble released three albums on Stiff, including a live album, initially for promotion only, and a further two on EMI America; all were well-received critically, and were accompanied by singles and extensive touring. Despite featuring regularly on radio playlists Any Trouble’s popularity wasn’t reflected in record sales, and they disbanded in 1984. They re-formed briefly in 2007 to record a new album Life in Reverse, released again through the re-constituted Stiff Records in the UK, playing a headline gig to support it at the Jazz Cafe, London, England.

In 1984, shortly after the release of Any Trouble’s fifth album Wrong End of the Race, Gregson saw vocalist Christine Collister perform at Poynton Folk Club, Cheshire, England. After the demise of Any Trouble, Gregson recorded a solo album (Strange Persuasions) and invited Collister to sing on it. Shortly after this, Richard Thompson asked Gregson to sing on his album Across a Crowded Room; at Gregson’s suggestion, Collister was enlisted for vocal duties, leading to her joining the Richard Thompson Band.

Demand for Gregson’s services as a record producer and session musician grew throughout the 1990s. He released Welcome to the Workhouse, his second solo project, in 1990, and by October 1992, was performing as a solo artist. As of January 2015, Gregson had released on CD 10 solo albums and one solo Best of collection plus two digital-only releases: the original recordings for his I Love This Town album and a stand-alone collection of songs recorded by Gregson for Any Trouble’s Life in Reverse but not included thereupon.

By 1992, Gregson and Collister went separate ways after recording a fifth and final album The Last Word; the supporting tour proved to be their most successful. A CD compilation celebrating Gregson’s and Collister’s career, The Best of Clive Gregson & Christine Collister, was released by Gregson & Collister Recordings through Gott Discs in 2006.

In 1993, Gregson relocated from the UK to Nashville, United States. In 2003, his career suffered a hiatus of several months after he broke his arm and shoulder in a fall from a ladder. He made a full recovery and continues to record and tour extensively in countries including the UK and Japan from his base in the USA, having moved to Houston, Texas, in the early 21st century. This fall wasn’t the first significant accident in Gregson’s life – as a child he was hospitalised with serious injuries after being hit by a car while crossing the road in Cockbrook, the area of Ashton-under-Lyne where he was raised. Gregson claimed that watches wouldn’t work reliably on his wrist after he left hospital, attributing this to metalwork used to pin bones.

Gregson’s reputation as a songwriter has led to his songs being recorded by artists, including Nanci Griffith (I Love This Town), Kim Carnes (Touch and Go), Fairport Convention (Home Is Where the Heart Is), Claire Martin (Could This Be the One?), Norma Waterson (Fred Astaire) and Smokie (Northern Soul). Gregson’s I Love This Town was recorded as a duet by Nanci Griffith and Jimmy Buffett in 2006, becoming a radio hit in the UK and U.S.

In 2007, Gregson was musical director for the Dennis Locorriere Hits and History Tour, which features on the Hits and History Tour Live DVD. Since 2010, Gregson has become a regular opening act for Jools Holland.

In 2011, Gregson joined forces with guitarist Mark Griffiths and Andy Roberts to form 3 Boxes, an instrumental guitar trio, to play a series of gigs and record an album of original material. The three had worked together in the group Plainsong in 1999.

In November 2013, the band re-formed for a one-off gig at the 229 Club, London, England, in support of the release of the three-CD set The Complete Stiff Recordings 1980–1981

In 2013, 3 Boxes released their only album to date Strings Attached, including only material written by the three members, all instrumentals for three acoustic guitars recorded live in the studio by producer John Wood.

In 2014, they recorded Present Tense, playing a short tour in December 2014, which included Band on the Wall, Manchester, England on 2 December 2014. plus dates in Newcastle upon Tyne, England, Birmingham, England, the 229 Club, London, England, and the Purple Weekend Festival, in León, Spain.