In July 1963, aged 16 and armed with a single O-level in art, David left Bromley Tech to work as a "junior visualiser" at a commercial art company called Nevundy-Hurst, based in Old Bond Street. His job consisted of "doing paste-up and initial design for things like raincoats," he recalled in 1993. "I hated it." In 2003 he recounted that "My immediate boss, Ian, a groovy modernist with Gerry Mulligan-style short crop haircut and Chelsea boots, was very encouraging about my passion for music, something he and I both shared, and used to send me on errands to Dobell's Jazz record shop on Charing Cross Road, knowing I'd be there for most of the morning till well after lunch break. It was there, in the 'bins', that I found Bob Dylan's first album. Ian had sent me there to get him a John Lee Hooker release and advised me to pick up a copy for myself, as it was so wonderful. Within weeks my pal George Underwood and I had changed the name of our little R&B outfit to The Hooker Brothers and had included both Hooker's "Tupelo" and Dylan's "House Of The Rising Sun" in our set."

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Substantial evidence of Bob Dylan's influence on David's songwriting lay some years ahead, but the naming of his new band betrayed a growing interest in the pioneering sounds of rhythm and blues and, as Bowie would later reflect, both Dylan and Hooker "became an integral part of what I tried to do eventually." The Hooker Brothers were a trio consisting of David, George Underwood and drummer Viv Andrews (later to play on The Pretty Things' first two hits, both covered by Bowie on Pin Ups). In the summer of 1963 they secured the first of David's many gigs at Peter Melkin's Bromel Club at the Bromley Court Hotel, and also played at the Ravensbourne College of Art, where George was now a pupil. "This was a group of sixteen and seventeen-year-olds playing blues," recalled Underwood. "Everything we did was copied, but not very well. Such songs as "My Momma Done Told Me"."

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David experimented continually with band names, changing his mind from week to week and designing posters for gigs both real and imaginary: among The Hooker Brothers' other names were The Delta Lemons, Dave and the Bowmen, The Bow Street Runners and Dave's Reds & Blues, the latter a coded reference to speed and barbiturate pills and, as David recalled in 2000, "a sad and clumsy allusion to R&B." It appears that the band had more names than gigs, only performing a total of three or four times before Viv Andrews departed. Meanwhile David continued to play with The Kon-rads until the end of 1963, and early the next year he played a couple of dates with The Wranglers, a group with whom The Kon-rads had shared a bill the previous November. By the beginning of 1964 David had parted company with The Kon-rads, and he once again joined forces with George Underwood to form the group with whom he would cut his first ever disc.