At Chess, Williams met Howlin’ Wolf , recently arrived in Chicago from Memphis, and was hired by Wolf as the first guitarist in his new Chicago-based band. A year later Hubert Sumlin moved to Chicago to join Wolf’s band, the dual guitars are featured on some Howlin’ Wolf’s recordings. Williams also provided backing on Otis Spann’s session.
Williams’ solo career began in December 1955 with the upbeat saxophone-driven “Lookin’ For My Baby” . By this time, Williams was a highly sought after session guitarist, his virtuosity in this capacity is well illustrated by his blistering lead guitar work on Bo Diddley’s ”Who Do You Love?“ , a hit for Checker Records in 1956. (Rock musician Marshall Crenshaw listed Williams’ guitar solo on ”Who Do You Love" as one of the greatest guitar solos ever recorded). Other notable session work from the 1950’s includes lead guitar parts for Billy Boy Arnold’, Jimmy Rogers, Jimmy Witherspoon, Otis Rush.
In 1957, Williams released “You May” with the inventive b-side instrumental “Lucky Lou” , the extraordinary opening riff of which Otis Rush copied on “All Your Love (I Miss Loving)” . Further evidence of Williams’ influence on Rush (they played on a number of sessions together) is Rush’s solo on Buddy Guy’s 1958 debut, “Sit And Cry (The Blues)” , copied almost exactly from Williams’ "You May".
The frequency with which Williams found his distinctive guitar phrases being copied without credit led to increasing disenchantment with the music business. When the distinctive riff he created for Billy Stewart’s 1956 Argo release, “Billy’s Blues”, was appropriated by Mickey Baker for the Mickey & Sylvia hit, “Love Is Strange” , Chess Records took legal action. At the conclusion of the case in 1961, Williams gained neither credit nor compensation. “I was ripped off,” Williams later told John Sinkevics in the Grand Rapids Press.[ In the early 1960s, Williams was making a living gigging with his Big 3 Trio (distinct from Willie Dixon’s group of the same name), but by the end of the decade, he had retired from the music industry altogether. He studied electronics and eventually became a technical engineer for Xerox, his job for over 25 years.
Only after his retirement did he consider picking up his guitar again, which had laid untouched under his bed all the while. “One day my wife said if I started playing again I might feel better about life in general,” he told Hoekstra of the Chicago Sun-Times. In March of 2000, he went to see his old friend Robert Jr. Lockwood play, and grew nostalgic for his music days. Back at home, an old tape of himself playing moved him to tears and inspired him to pick up his guitar again. He returned to playing in public in June of 2000, when he was featured at the Chicago Blues Festival . He gained much encouragement in this period from Dick Shurman , who eventually produced his comeback album, ”Return of a Legend” (2002), on which his bold playing belies his thirty-year break from music. “He plays with a verve and vigor that sound as good today as it did on the classic records” wrote Vintage Guitar magazine . The album “You Left Me In The Dark” followed as well as sessions with the Mannish Boys.
Williams continues to perform around the world, mainly at large blues festivals, and can often be seen sitting in with blues guitarist Billy Flynn at Chicago club appearances.