By the end of the 1950s, Bickert was regularly working as a studio musician in Toronto, recording on commercial and jazz sessions.Bickert's commercial, radio, and television work increased through the 1960s, though he also continued to play jazz gigs at night.

During these years, Bickert first worked with Rob McConnell and many of the Toronto jazz musicians who later became the core of McConnell's Boss Brass big band. The Boss Brass was a part-time band led