Matthews moved from his native South Africa to New York when he was just two years old. When his father died he moved back to Johannesburg with his mother, where he finished high school. He finally settled back in Charlottesville, Virginia, and assembled his self-titled, multiracial band in 1990. Matthews (b. 9 January 1967, Johannesburg, South Africa; guitar/vocals), Leroi Moore (reeds/saxophone), Boyd Tinsley (violin), Steffan Lessard (b. 4 June 1974; bass), and Carter Beauford (drums) forged a vibrant, individual sound from their wide instrumental range, with the eclectic mix significantly complementing Matthews' own expanded world view. Together they built a formidable reputation on the back of a punishing touring schedule, which helped their self-produced and financed debut, 1993's Remember Two Things, sell over 150,000 copies.

In the wake of their debut's success the band was afforded the luxury of picking from the major labels. Eventually choosing RCA Records (who offered the most malleable recording contract), their major label debut, Under The Table And Dreaming, produced by Steve Lillywhite, entered the Billboard charts in 1994 at number 34. Because of the record's continued success, the band was faced with the problem of having new material written to perform at gigs and yet having an album that was still selling strongly. They wisely issued Crash, to satisfy demand for a new product and it immediately went to number 2 in the US chart, confirming their arrival as one of the most successful rock acts of the 90s. The 1998 album Before These Crowded Streets debuted at US number 1, deposing the Titanic soundtrack album in the process, but showed little sign of any creative progress, indicating that they may have become victims of their own astonishing success. Their popularity was confirmed when Live At Luther College, a 1996 recording by Matthews and collaborator Tim Reynolds, debuted at number 2 in February 1999. Everyday rather predictably went straight in at number 1 on the US charts in March 2001, a feat matched by the following July's Busted Stuff. In 2005 Stand Up also reached the top slot. Such popularity in the USA is in bizarre contrast to the lack of interest in Europe.