In September the following year Wilson, on harmonica and saxophone, and Barry Palmer, on lead guitar, joined a neo-Blues group, Harem Scarem, alongside Peter Jones on drums, Charles Marshall on guitar, Christopher Marshall on lead vocals and Glen Sheldon on bass guitar. This line-up recorded their debut studio album, 'Pilgrim's Progress' for Au Go Go Records, which was released in December 1986.
While a member of Harem Scarem, Wilson provided harmonica on Paul Kelly and the Coloured Girls' debut album, 'Gossip' (September 1986). By May 1987 Wilson had left Harem Scarem, he joined Kelly's 45-date tour of North America promoting 'Gossip'. Wilson acknowledges Kelly for extending his repertoire beyond harmonica, "I was asked on as a sax player too and I didn't play all that much sax when Kelly asked. But he had that faith in me that I'd get my act together". During that year Wilson also guested on Hunters & Collectors album, 'What's a Few Men?' (November 1987), on Paul Kelly and the Coloured Girls' next album, 'Under the Sun' (December), and he played with hard rockers, X.
Wilson formed his own band, Crown of Thorns, with Barry Palmer, and Chris Rodgers on double bass, bass guitar and fiddle, in 1987. Stuart Coupe of The Canberra Times described the group's sound as "a diverse amalgam, recalling everything from Tim Buckley to Captain Beefheart and American blues". While Wilson felt his group was not only a blues band as "there's elements of country and straight rock 'n' roll". Their debut release was a six-track EP, 'Gnawing On The Bones Of Elvis', which was produced by the band and appeared in April 1988. Australian musicologist, Ian McFarlane, noted it was "sparsely recorded … which mixed one side of electric blues including Willie Dixon's ''Bring It on Home'', and one side of acoustic folk tunes".
Crown of Thorns issued a studio album, 'Carnival' (February 1989), using a lineup of Wilson, Palmer, Rodgers, joined by Justin Brady on violin, Barbara Waters on guitar, vocals and mandolin (ex-Hollowmen), and former band mate, Jones on drums. The album was produced by Wilson and Waters with Chris Thompson. McFarlane described it as a "more fully realised work than the debut. It mixed blues, country and folk with a great deal of verve and authority". It contained Wilson's composition "The Ballad of Slim Boy Fat", which was a highlight of the album with its spectacular blues/gospel style. In 1990 the group released another studio album, 'Babylon', with Wilson, Rodgers, and Waters joined by Ashley Davies on drums (ex-White Cross).
Late in 1990 he formed a briefly existing group, The Pub Dogs, with Wilson on harmonica and lead vocals, Barry Palmer on electric and acoustic guitars, Graham Lee on pedal steel guitar and backing vocals (ex-The Triffids); and Marko Halstead on acoustic guitar, mandolin and backing vocals (of The Blackeyed Susans). They issued a live EP, 'Scatter's Liver: Pub Dogs Live on the Wireless' in the next year on Shock Records, which had been recorded at radio station Triple J's studios in Melbourne on 22 October 1990. In August 1991 Wilson provided lead vocals for Robin Casinader's debut solo album, 'All This Will Be Yours'.
During 1992 Wilson formed the Chris Wilson Band which released an EP, 'The Big One' in May and a studio album, 'Landlocked' in June. The line-up were Wilson and Rodgers with Jen Anderson on violin (The Black Sorrows), Rebecca Barnard on backing vocals (ex-Stephen Cummings Band), Peter Luscombe on drums (The Black Sorrows), and Shane O'Mara on guitars (Stephen Cummings Band). Los Angeles Times ' reviewer, Mike Boehm, felt that on the album "he sometimes becomes bogged down with self-conscious attempts at poetic imagery, and that high-voltage vocal style can seem strident".
During June Wilson and Crown of Thorns performed a combined tour promoting recent material. Laurie White caught their gig at Tilley's which "a privileged few will remember for an age (if only I'd taken a Walkman like one lucky bootlegger)" with Wilson described as "a huge writhing gospel cyber punk, who sings and plays harp with such venom and power it's impossible to ignore him against melancholy songs (reminiscent of Archie Roach at his most tearful). The change in gear is exhilarating if not frightening". Wilson followed with another EP, 'Alimony Blues', in October; it had a cover version of Booker T. Jones' "Born Under a Bad Sign", which McFarlane declared had Wilson's vocals "backed by O'Mara's blistering guitar work and was one of the finest renditions ever committed to record".
In March 1993 Wilson and fellow Australian singer-songwriters Barnard, Kelly, Archie Roach, Deborah Conway and David Bridie each performed a set at a Hollywood concert, The Melbourne Shuffle. Boehm described Wilson as "a big, denim-clad slab of a man with a shaven head and the look of a street tough or a stevedore. In contrast to such reserved performers as Kelly ... he had a taste for the monumental. His big, rangy, high-impact voice supported his flair for the dramatic flourish and the grand gesture". As a performer Wilson showed "a dry, laconic wit between songs, he was a fervent, let-it-all-out wailer when he began to sing".
At the ARIA Music Awards of 1993, held in April, Wilson was nominated for Best Male Artist and Breakthrough Artist - Album for 'Landlocked'. In June that year Wilson, Charlie Owen, and three former members of The Triffids: David McComb, Robert McComb and Graham Lee guested on Acuff's Rose's debut studio album, 'Never Comin' Down'. On 20 May 1994 Wilson's performance at the Continental Hotel in Prahran was recorded for 'Live at the Continental', which was released in October. The album provided Wilson with another nomination for Best Male Artist in October 1995. Wilson toured extensively and played at many festivals, both in Australia and overseas, and has shared stages with Bob Dylan, and with Johnny Diesel. He provided backing vocals on the Merril Bainbridge song "Under the Water" for her album 'The Garden' (1995).
In March 1996 Wilson Diesel issued a collaborative album, 'Short Cool Ones' on Mushroom Records, with Wilson on lead vocals and harmonica, and Diesel on lead vocals and lead guitar. 'Short Cool Ones' peaked at #18 on the ARIA Albums Chart. McFarlane described it as including "15 soul and R&B standards ... and a sole original, ''Other Man'". "Other Man" was written by Diesel (aka Mark Lizotte). Other performers were Dean Addison on bass guitar, Angus Diggs on drums, and Rob Woolf on keyboards and backing vocals. Paul Petran of Radio National's Live on Stage felt 'Short Cool Ones' was "one of the most successful blues albums in Australian history".
Wilson's next solo album, 'The Long Weekend', appeared in March 1998 as a 2× CD. McFarlane noted the album had "22 excellent tracks, it drew on blues, gospel and country elements". In May Wilson supported Kelly at the Metro in Melbourne where Wilson was crashing through a slightly hollow mix with a bunch of the good stuff, picking the eyes out of his recent Long Weekend thing, and throwing in some older selections – the 'best done by Elvis' Mystery Train being a big blow, as is the pump action 'Shoot Out at Seven Eleven', while the big ballady 'Too Many Hearts' again is a glory and must be a single, surely. At the ARIA Awards that year he received another nomination as Best Male Artist, for 'The Long Weekend'. In November he appeared at the Mushroom 25 Concert both as a solo artist and in Wilson Diesel.
In January 1999 Wilson was a support act for Elvis Costello on an Australian tour. By 2000 he had formed Chris Wilson and the Spidermen with Rodgers, Shannon Bourne on guitar, and Dave Folley on drums. Wilson issued a solo album, 'Spiderman', which was recorded at Studio 335, Southbank with Wilson, O'Mara and Thompson co-producing; O'Mara also guested on two tracks. Rhythms Magazine 's readers' poll rated 'Spiderman' as the Best Australian Blues Album of 2000. Melbourne Blues Rock website's Tom Slingsby reviewed the album in September 2011 and noted it was "a mix of covers and originals. … The covers are given a real personal touch one could easily think Wilson and gang had crafted the songs themselves". Slingsby felt the "production allows both the guitar and harmonica to stand out on tracks, trade off licks, and then fall back to accompany the other instruments. Overall the album has a strong dynamic range with slower, sultry songs inserted amongst the more lively tracks without dropping off in feel".
During May 2002 Wilson recorded his next album, 'King for a Day' (July 2002), at two studios in Melbourne with Kerryn Tolhurst producing. Along with Bourne, Folley and Rodgers, the album featured Tollhurst (guest guitars, piano, mandolin and tipple), Cindy Boste (guest lead vocals), Sarah Carroll (guest lead vocals) and Skip Sail (guest banjo). In March 2003 Richard Sharman of I-94 Bar website reviewed Chris Wilson and The Spidermen's gig at the Bridge Hotel in Sydney and found that Wilson's "voice was magnificent ranging from soft tenderness to a bellowing roar that raised shivers at the back of my neck. His voice sounded better than ever and his harp playing was superb – this boy can play!" On 26 October 2013 Wilson Diesel reunited to perform the entire 'Short Cool Ones' album at the Sydney Blues & Roots Festival. On 30 October 2019, Chris Wilson was inducted into the Blues Music Victoria Inc Hall of Fame as the 2019 People's Choice, Victorian Blues Legend. In 2020, Wilson was inducted into the Music Victoria Awards' Hall of Fame. He died 16 January 2019, having been diagnosed with pancreatic cancer in 2018.
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