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One of Ian's first forays into music was a talent competition at Butlin's holiday camp, performing Blue Moon as part of a skiffle group with Colen York and Colin Broome. York and Broome came from Northampton, and were in a band called The Apex. Ian soon moved to Northampton and joined the Apex on rhythm guitar.

Ian struck out on his own in 1963, forming Hurricane Henry and the Shriekers with Tony Marriott and guitarist Julian Coulter. The Shriekers worked steadily in Northampton, and by 1965 had picked up Freddie 'Fingers' Lee as a pianist and frontman.

Ian moved to London in 1966, where he teamed up with guitarist Miller Anderson, drummer Dave Dufort, and keyboard player Dante Smith to form The Scenery. By 1967 Smith and Dufort had left, and John Vernon Smith had moved in on drums. The Scenery recorded some material with Bill Farley at Regent Sound, which was released without the band's knowledge in France and Japan.

By early 1968, The Scenery had run its course and Miller Anderson joined Dave Dufort in Paper Blitz Tissue. Ian hooked back up with Freddie Lee in At Last The 1958 Rock and Roll Show, along with drummer Pete Philips and guitarist Chris Mayfield. The group got a regular booking at The Angel in Edmonton, and drew interest from both Chrysalis and NEMS. Mayfield was soon replaced by Miller Anderson, and the group released a single on CBS called I Can't Drive.

As the short-lived Rock and Roll Revivial began to wane, At Last the 1958 Rock and Roll Show changed its name to Charlie Woolfe and released a final single on NEMS, Dance Dance Dance.