50 free Dave Matthews Band trivia questions with answers — music quiz, new questions added Aug 2026.
This Dave Matthews trivia quiz covers the band from Miller's Bar in Charlottesville to the Rock and Roll Hall of Fame. It asks about the founding five, the demo tape and the first shows at Trax, the name the band almost took, Remember Two Things and the Bama Rags label, and the run of RCA albums from Under the Table and Dreaming through Crash and Before These Crowded Streets. There are questions on the Grammy, the leaked Lillywhite Sessions and Busted Stuff, Everyday with Glen Ballard, Stand Up, and the loss of LeRoi Moore. It also covers the touring life that made the band: Red Rocks and the Gorge, the taping culture, the Chicago River bus incident, the Warehouse fan club, Boyd Tinsley's exit, and the record seven straight No. 1 debuts capped by Come Tomorrow. About a third are easy for anyone who has been to a summer show, a third are medium, and the rest are for people who know what 'Dumwelah' means. Every answer was checked against Wikipedia and the interviews it cites, and each question carries the sentence that establishes it. If you think one is wrong, use the report button and we will look again.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Dave Matthews Band formed in 1991 in which city?
Charlottesville, Virginia
The band still marks its birthplace with shows at the John Paul Jones Arena there.
Q 02What was Dave Matthews doing for a living in 1990 when a lawyer friend persuaded him to record a demo?
Bartending at Miller's
He watched LeRoi Moore play jazz there while serving the musicians whiskey.
Q 03Which drummer, then playing on a BET jazz show, was the first musician Matthews approached?
Carter Beauford
Matthews said he went to him not because he needed a drummer but because he was 'the baddest thing I'd ever seen'.
Q 04Which instrument did founding member LeRoi Moore play?
Saxophone
A local jazz musician with the John D'earth Quintet, he was the second recruit after Beauford.
Q 05Bassist Stefan Lessard was how far through his studies when he joined the band?
A junior at the university
UVA jazz director John D'earth recommended him; he was still a teenager.
Q 06Boyd Tinsley was originally brought in just to add fiddle to which one song?
Tripping Billies
Matthews said the band had no plans for a violinist, but 'it just clicked' and Tinsley stayed until 2018.
Q 07The band's first keyboardist, who left in March 1993, was a waiter at Miller's named what?
Peter Griesar
His farewell show at Trax is known to fans as 'Big League Chew'.
Q 08The band considered calling itself 'Dumwelah', a Tswana word meaning what?
Hello
Nobody was keen; the name Dave Matthews Band arrived when someone added 'band' to a booking or a flyer.
Q 09Which Charlottesville club hosted the band's regular Tuesday-night shows, widely traded on tape?
Trax
The earliest known show, a March 1991 benefit, was rediscovered there via a tape in 2010.
Q 10The band's long-time manager, Coran Capshaw, first knew them as owner of which Richmond venue?
The Flood Zone
Capshaw took over from Charles Newman and went on to found Red Light Management.
Q 11The band's first official release, Remember Two Things (1993), came out on which of their own labels?
Bama Rags
It debuted as the highest independent entry on the college charts and went platinum in 2002.
Q 12The 1994 major-label debut Under the Table and Dreaming was dedicated to whom?
Matthews's sister Anne
Anne was killed by her husband in a murder-suicide in 1994; the album went six-times platinum.
Q 13Which Blues Traveler frontman plays harmonica on 'What Would You Say'?
John Popper
The song was the band's first commercial hit, alongside 'Satellite' and 'Ants Marching'.
Q 21The abandoned 2000 recordings that leaked online in March 2001 are known to fans as what?
The Lillywhite Sessions
A fan campaign to release them led to Busted Stuff, which reworked much of the material in 2002.
Q 22The Busted Stuff single 'Where Are You Going' was used in which 2002 Adam Sandler film?
Mr. Deeds
The album was produced by Stephen Harris, Lillywhite's former engineer.
Q 23In August 2004, a band's tour bus dumped waste off a bridge onto a tour boat in which city?
Chicago
The driver pleaded guilty; the band donated $100,000 to local causes and paid $200,000 to settle a lawsuit.
Q 14The band's only Grammy win, in 1996, was for which song?
So Much to Say
The award was Best Rock Performance by a Duo or Group; Crash and 'Too Much' were nominated the same year.
Q 15The band's first full-length live album, released in 1997, was recorded at which venue?
Red Rocks Amphitheatre
Live at Red Rocks 8.15.95 features Tim Reynolds on electric guitar.
Q 16Which singer guests on Before These Crowded Streets alongside Béla Fleck and the Kronos Quartet?
Alanis Morissette
The 1998 album sold more than 900,000 copies worldwide in its first week.
Q 17What was the lead single from Before These Crowded Streets?
Don't Drink the Water
'Stay' and 'Crush' followed; 'Crush' picked up a Grammy nomination for Best Pop Collaboration with Vocals.
Q 18The live album Listener Supported was recorded in September 1999 for a special on which broadcaster?
PBS
The East Rutherford show also became the band's first DVD.
Q 19Everyday (2001) was written and produced with which collaborator known for Jagged Little Pill?
Glen Ballard
Its pop-rock sound and short songs split fans; Carter Beauford said it did not showcase the rest of the band.
Q 20Which guitar legend guested on the Everyday sessions in Los Angeles?
Carlos Santana
The singles 'I Did It', 'Everyday' and 'The Space Between' all charted on the Hot 100.
Q 24Which actress and long-time fan appears in the video for 'Dreamgirl' from Stand Up?
Julia Roberts
Stand Up, produced by Mark Batson, debuted at No. 1 with 465,000 sales in May 2005.
Q 25The band's Labor Day 2006 concert at which venue drew 64,468 people, the largest crowd in its history?
The Gorge Amphitheatre
The Gorge in George, Washington, remains the site of the band's traditional Labor Day three-night stand.
Q 26Which guests featured at the band's September 2007 free concert for Virginia Tech?
John Mayer, Phil Vassar and Nas
More than 50,000 attended; two days later a Piedmont Park benefit in Atlanta became the city's biggest one-day concert.
Q 27The band's saxophonist died in August 2008 from complications of what?
An ATV accident on his farm
Jeff Coffin of the Flecktones filled in on the tour and later joined permanently; only two shows were cancelled.
Q 28In the title of the 2009 album Big Whiskey and the GrooGrux King, who is said to be 'the King'?
The band's late saxophonist
The album was made in New Orleans after the loss and was nominated for Album of the Year at the Grammys.
Q 29Which saxophonist, from Béla Fleck and the Flecktones, took over after the founding sax player's death?
Jeff Coffin
Trumpeter Rashawn Ross had joined the touring line-up in 2005 and 2006.
Q 30Which guitarist, a longtime collaborator, became a permanent member of the band in 2008?
Tim Reynolds
Reynolds had guested since 1993 and made the acoustic duo albums with Matthews.