“This isn’t his first last gig and it won’t be his last last one either” was the best joke I heard when friends and fans gathered at the Railway Inn for a valedictory performance from cult singer-songwriter Chris T-T.

Winchester-raised Chris Thorpe-Tracey (styled T-T) has always been subject to affectionate ribbing for his appearance and tendency to self-aggrandise, particularly by those of us who’ve known him since the early 1990s when he was collaborator and impresario to the city’s up-and-coming musicians.

For many, that affection crystallised into admiration as T-T mined reserves of ambition to forge a 20-year recording career, while most of us gave up music to pursue more lucrative jobs inspired, in my case, by the creative example set by artists like him who stubbornly refuse to compromise.

While a handful of the former-Wintonians T-T has worked with, including million-selling folk musician Jon Boden and Razorlight drummer Andy Burrows have gone on to commercial success, T-T enjoyed a cult following always on the cusp of greatness, a state apparently suited to a personality that swings wildly from hubris to contrition.

The T-T persona was on full display as he punctuated highlights from his 10-album back catalogue with Springsteen-esque anecdotes about near misses, disappointments and friends made along the way; not least the singer Frank Turner whom he credits with reigniting his career a decade ago and has been sort of Bob Dylan to his Woody Guthrie.

Although his oeuvre mixes punk, shoegaze and psychedelia, it’s his political balladeering that leaves the strongest impression, with songs like Love Me I’m a Liberal and The Huntsman Comes a-Marching asking questions about gentrification, class and the search for an inclusive English identity, more relevant to his home town than ever.

The desire to shake off his “punk troubadour” persona has motivated Chris T-T’s decision to retire as a solo-artist to pursue new projects in music, journalism and politics from Brighton, where he now lives. Speaking to him after the gig, I sensed restlessness with a job unfinished but the example he has set in promoting music, creativity and political awareness mean that in his case, the journey has been the destination.

Mark Lowe

Twitter: @markrlowe