[6] At age two, Matthews moved with his family to Yorktown Heights, New York, where his father, a physicist, started working for IBM.

[11] Upon Matthews's graduation from secondary school in 1985, he was faced with conscription into the South African military just as civil disobedience to the practice was becoming widespread.

[10] Matthews met local star (and future collaborator) Tim Reynolds through mutual friend, Nic Cappon.

[17] After writing his first few songs, including "I'll Back You Up", "The Song That Jane Likes" and "Recently", Matthews formed Dave Matthews Band in early 1991 with LeRoi Moore, Carter Beauford, Stefan Lessard, Peter Griesar (who left the band in 1993), and Boyd Tinsley while working at Miller's as a bartender.

[18] The band's first show was on March 14, 1991, as part of a benefit for the Middle East Children's Alliance at Trax Nightclub in Charlottesville, Virginia.

Both Fleck and the Flecktones' bassist Victor Wooten have made numerous live appearances and in studio with the Dave Matthews Band.

[26] They also appeared together on the musical television show CMT Crossroads,[27] where the two performed Matthews's "Gravedigger" and the folk song "Long Black Veil".

Before he was known as a musician, Dave Matthews was an amateur actor, appearing onstage in several productions at Charlottesville's Offstage Theatre and Live Arts theater[30] in the early 1990s; the role for which he is best remembered is as a used car salesman in Offstage Theatre's "Just Say No," directed by John Quinn, co-starring Kylie Suture.

[33] In 2008, he appeared in the Adam Sandler movie You Don't Mess with the Zohan as a racist redneck character named James.

In 1999, Matthews purchased more than 10 acres of land in Albemarle County, Virginia, known as Blenheim Farm, to preserve its historical significance.

This led to the formation of a band named The Nauts with Matthews, Dylan, Blade, and the Sexton brothers as members.

[48] He joined the Farm Aid board of directors in 2001,[49] to serve alongside fellow musicians Willie Nelson, John Mellencamp and Neil Young to raise money for family farmers in the United States.

[50] Matthews published an Internet video before the 2000 U.S. presidential election, urging viewers to vote without advocating any candidate.

Although his music often explores political and social issues, Matthews refrained from public campaigning for presidential candidates until 2004.

He cast his support strongly with Democratic nominee John Kerry, performing at political events including the Vote for Change tour.

[51] On April 6, 2008, he and Tim Reynolds played a concert titled "Change Rocks"[52] at Indiana University to encourage students to register to vote.

[59] On May 10, 2012, Matthews entertained a sellout crowd at the Paramount Theatre in Seattle where President Obama was hosting a campaign fundraiser.

[60] In a September 28, 2015, interview with Rolling Stone, Matthews said that "when I hear someone like Bernie Sanders talking, I think there's a hope.

"[61] Matthews performed at a San Francisco rally for Sanders during the 2016 presidential primaries and later, during the general election campaign.

[62] On October 30, 2021, Matthews performed at a Democratic get out the vote event in Charlottesville, Virginia with gubernatorial candidate Terry McAuliffe.

Two shows have been released as part of the Dave Matthews Band's DMBlive series available only for online download.