Anderson attended Montclair High School where he learned to play the trombone. He later attended the Berklee College of Music, and took up bass guitar. He joined The Centurions, which brought him to the attention of Chris Wood of Traffic, who invited him to play on the band's next album.The Traffic album involvement never materialized, but led to Anderson becoming employed by Traffic's record label Island Records, leading to him being asked to play lead guitar on Bob Marley & The Wailers' Natty Dread sessions.

Anderson played lead guitar on "Crazy Baldhead" and on the Live! album, remaining with the band until 1976, when he joined Word, Sound and Power, backing Peter Tosh on the albums Legalise It and Equal Rights. He returned to Marley's band and played on the Survival and Uprising albums. After Marley's death, Anderson continued to tour with The Wailers Band, In 2008 he formed his own band The Original Wailers (T.O.W) with Junior Marvin who was also tour and recorded with Marley until his passing.