Despite his difficulties, in 1984 Bill was given his first opportunity to appear on the Late Night with David Letterman show, courtesy of Jay Leno, who recognised his unique talent. Despite such breaks, Bill’s drug and alcohol abuse continued and in 1986 finally took its toll financially when he found himself bankrupt.
A further opportunity came however in 1987 when Rodney Dangerfield asked him to appear on his Young Comedians Special. In the same year, realising the seriousness of his addiction to alcohol and drugs, Bill moved to New York to start afresh. Loving the energy and vibrancy of New York, he worked steadily toward solidifying his reputation with audiences and entered one of the most productive periods of his career. Working in excess of 300 gigs per year, and with new manager Jack Mondrus, in 1988 Bill filmed his first video Sane Man in front of a loyal audience of fans in Austin, Texas, and began attending AA meetings as his journey to sobriety began.
1990 marked an important benchmark for Bill in creative terms with the release of his first album Dangerous, titled in keeping with his acknowledgement of the controversial but vital nature of the ideas he was incorporating into his act. Also in 1990, Bill delivered landmark performances in his HBO special One Night Stand and the Montreal Just for Laughs festival.
A second performance for Just for Laughs later that year resulted in the filming of the now revered video Relentless. Performing that same year in London for the first time as part of the production Stand Up America, Bill proved popular and was given his first taste of success in the UK, winning also the prestigious Critics Award at the Edinburgh Festival.
Bill’s profile within the UK was boosted further during his popular 1991 tour of the UK and Ireland, which saw sell-out shows across the country.