Webb attended secondary school with Lee Harris, and the two became good friends. They played in the reggaeband Eskalator before being recruited to form Talk Talk in 1981. Webb played bass for Talk Talk until 1988.
In the early 1990s he and Harris formed .O.rang. In the early 2000s he adopted the name "Rustin Man" and collaborated with Beth Gibbons on Out of Season (2002).