In the early 1990s, the band established a cult following through relentless touring, as well as their independent LP, Remember Two Things. After signing to RCA Records, Dave Matthews Band released Under the Table & Dreaming, a critical and popular smash that firmly established the band's style of pop-rock with improvisational leanings. This was followed by Crash (1996), another popular album. Live at Red Rocks 8-15-95 was released in 1997, resulting in a huge success. 1998's studio LP Before These Crowded Streets is arguably the band's most complex work. In 1999 the band released two live albums: Dave Matthews and Tim Reynolds Live at Luther College, from a 1996 acoustic concert played by Matthews and longtime friend guitarist Tim Reynolds, and Listener Supported, a concert from September 1999 that was also partially shown on PBS.
Arguments have raged throughout both the Dave Matthews Band's fanbase and online communities dedicated to discussing bands such as Phish and the Grateful Dead as to whether or not they are a true jam band. It's perhaps more accurate to state that the band's music and that of the many bands influenced by it is a breakaway sub-genre of jam band. Unlike many of their peers and contemporaries (most notably Phish), their live shows displayed their distinctively structural approach to songwriting in which the 'jam' generally took place within the boundaries of a song, rather than the traditional jam band approach, in which the song is often secondary to the improvisation. While Dave Matthews Band are unquestionably the driving influence behind this sub-genre as it exists today, the style arguably owes its roots to Atlanta, Georgia's Widespread Panic.
During the year 2000, the band set up its own recording studio in a large house in the country outside Charlottesville, Virginia. With longtime producer Steve Lillywhite at the helm, the band began recording a set of songs which had been previewed both on the previous band tour and on Matthews' acoustic tour with Tim Reynolds. Heavily influenced by personal conflicts, notably the death of his uncle and his resulting alcoholism, the songs recorded with Lillywhite rank as possibly the darkest Matthews has ever written. The album was scrapped in August 2000, for reasons which are still unknown. The most likely theory is simply that the band was unhappy with the atmosphere of the recordings and uncomfortable with the subject matter, though many have speculated that executives at RCA rejected the album because of a lack of potential radio hits.
In October 2000, Matthews began writing with Glen Ballard, most famous for his work with Alanis Morissette. The band soon joined Matthews in a Los Angeles studio, quickly recording what was to become Everyday. Some members of the band have expressed their disappointment with the way the sessions were conducted. Drummer Carter Beauford's sarcastic jibe that the band had "charts and everything" ready for them shines light on a session where the band, which had in the past collectively composed its music, was turned into a backing band for Matthews with no creative input. Everyday was a huge commercial success upon release - the singles "I Did It", "The Space Between" and "Everyday" gaining the band an even larger level of popularity both due to commercial sheen and a highly polished, electric sound. Hardcore fans, however, reviled the album. Its poppy, slick sound was a huge departure from the band's previous work and the complete antithesis of the songs recorded with Lillywhite.
Soon after Everyday's release, a bootleg CD featuring these songs made their way to a fan, who, after much debate, decided to upload the songs to the Internet for the benefit of the fanbase. The songs, quickly labeled The Lillywhite Sessions spread like wildfire, mostly thanks to fans hosting the files on the popular file sharing service Napster. The lost album was almost universally lauded by the band's fanbase, leading to a group of fans starting a campaign to "Release the Lillywhites".
In 2002, the band partially granted their fans' wishes. They entered the Plant studio in Sausalito, California to record Busted Stuff. The resulting CD featured most of the songs featured on the Lillywhite Sessions along with new songs such as "You Never Know" and the hit single "Where Are You Going", which had been previewed during a handful of Matthews' solo acoustic concerts. Busted Stuff received moderate critical and commercial success and was well-received by the band's fanbase. Later that year the band released its fourth live album, Live at Folsom Field, Boulder, Colorado, recorded July 11, 2001. The live release highlighted songs from both Everyday and Busted Stuff.