- Grew up in South Africa, New York and Virginia.
- Began playing guitar at age 9.
- At age 19, began working as a clerk at IBM in the same research center where his father had been employed.
- After moving to Charlottesville, VA, he performed as an amateur actor in several regional productions.
- Formed his eponymous band in 1991 in Charlottesville, VA, and the group made its first appearance on Earth Day of that year.
- Released debut album Remember Two Things in 1993.
- In 1996, won his first Grammy for his vocal performance on "So Much to Say."
- In January 1997, his band played at President Bill Clinton's inauguration after his reelection.
- Established Bama Works Fund in 1999 to support charitable programs in Charlottesville, VA.
- In 2003, released his first solo album Some Devil, which contained the Grammy-winning single "Gravedigger," and made his big-screen acting debut in Where the Red Fern Grows.
- In 2004, formed Bama Works Village Recovery Fund to aid Asian tsunami victims.
- The band received the Chairman's Award at the 2004 NAACP Image Awards for its devotion to social and environmental causes.
- 2003, Grammy — Best Male Rock Vocal Performance: Winner
- 2010, CMT Music Awards — Collaborative Video of the Year: Nominee
- 1996, Grammy — Best Rock Performance by a Duo or Group with Vocal: Winner
- August Oliver — Son
- John Matthews — Father
- Anne — Sister
- Peter Matthews — Brother
- Val Matthews — Mother
- Grace Anne Matthews — Daughter
- Jane — Sister
- Stella Busina Matthews — Daughter
- Jennifer Ashley Harper — Wife
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