He studied guitar from his youth, and was writing songs and performing from his teen years.
The Hawks and Bob Dylan
By 1958, Robertson was performing in various groups around Toronto. In 1960, he met singer Ronnie Hawkins, who led a band called The Hawks after relocating to Canada from the United States.  Robertson joined The Hawks, who toured often, then split from Hawkins in 1963.
Bob Dylan hired The Band for his famed and controversial tours of 1965 and 1966, his first wide exposure as an "electric" rock and roll performer rather than his earlier folk sound. Robertson's distinctive guitar sound was an essential part of the music.
From their first album, Music From Big Pink (1968), The Band were praised as one of rock music's preeminent groups. Rolling Stone in particular lavished praise and coverage on The Band to an extent rarely seen before or since in the magazine.
Robertson sang only a few songs with The Band, but was the group's primary songwriter, and was often seen as the de facto bandleader. Drummer and singer Levon Helm would later claim that Robertson took too much songwriting credit for The Band's material.
In 1976, Robertson decided to break up The Band, reporting that he was profoundly by exhausted by nearly twenty years' worth of almost non-stop touring. In The Last Waltz, Robertson noted that he had been playing live rock and roll music nearly since rock and roll began.
The Band reformed in 1983, without Robertson.
Robertson has released four solo albums:
- 1987 Robbie Robertson
- 1991 Storyville
- 1994 Music for the Native Americans
- 1998 Contact from the Underworld of Red Boy