1996–2012: Continued success
In March 1996, Wilson Diesel released 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 No. 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, was released in March 1998 as a two CD set. 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 Music Awards of 1998 Wilson 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, Wilson 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 Tim 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 at two studios in Melbourne with Kerryn Tolhurst producing. King for a Day, which was released in July 2002. Along with Bourne, Folley and Rodgers, the album featured Tolhurst (guest guitars, piano, mandolin and tipple), Cyndi 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!"