Rafferty began his career as a member of the mid-1960s folk-rock group the Humblebums, which also included future comedy star Billy Connolly. When they folded he formed Stealers Wheel with his old friend Joe Egan, but the group was never able follow up the success of "Stuck In The Middle" and they broke up soon after the track hit big. "I was going through a very strange period in my life then," Rafferty told Rolling Stone in 1978. "I'd been living a dream for six or eight years and suddenly I woke up. I was a pretty scary kind of feeling. Perhaps I was on the edge of a nervous breakdown."
He eventually rejoined the group and they cut a new album with the legendary songwriting team of Jerry Leiber and Mike Stoller. The sessions were strained. "There was a generation gap and a culture gap," Rafferty said. "We didn't share a sense of humor or anything." The group split for good in 1975 and three years later Rafferty released his solo album City to City, which sold 5.5 million copies due to the massive hit "Baker Street" — best known for the saxophone hook by Raphael Ravenscroft. The famous sax solo was originally part of the melody and Rafferty thought he would sing it or play it on guitar, but ultimately he decided that it sounded best on the sax.
Rafferty didn't capitalize off the huge success of "Baker Street" due to his refusal to tour or even hire a manager. Minor hits "All Down the Line" and "City to City" followed, but by the mid-1980s he had faded into obscurity. Rafferty was rarely seen in public in recent years, though there were many reports in the British press about his battles with alcoholism.