Matthews had originally envisaged someone else singing his lyrics, but after writing his first few songs, including "The Song that Jane Likes" and "Recently", he started his own band. Matthews formed The Dave Matthews Band in early 1991 with Boyd Tinsley, Leroi Moore, Carter Beauford, and Stefan Lessard. The band performed his first gig on May 11, 1991, at a private terrace party held by Lydia Condor at the South Street Warehouse in downtown Charlottesville. What segregates the Dave Matthews Band apart from other festival veterans is the solid composition of catchy songs upon which all their instrumental explorations are based. Fans are really fond of him and particularly wait for Matthews' songs changing from one performance to another. What makes his fans go crazy is the fact, he knows the art of blending the hook-packed structure of their favorite songs with fresh improvisational jams. His cordial singing layers and random melodies are on top of bouncy chords that fit together in all manners. It can be easily compared to a sort of like rubber jigsaw puzzle pieces. Matthews also delicately incorporates some Latin rhythms and World Fusion into his bouncy Jam Rock/Pop, which provides a more sonic texture to his songs. The extra dimension that is achieved is also an added advantage. With such elements Matthews and his band confidently take risks playing live, which tends to make his performances (and bootlegs) a little more interesting and captivating than his polished and to some extent harmless studio recordings.

As one of the world’s most successful touring bands, Dave Matthews Band this season hit the road in support of their latest release, Stand Up. Starting in June, the band will embarked on a summer tour playing nearly 50 dates across the United States with a number of shows that were already sold out. Dave Matthews Band is one of the world's best live bands, that is put in one of the country's most beautiful concert settings. It did not come as a matter of surprise that "Weekend on the Rocks," the Dave Matthews Band (music)'s two-disc document at Colorado's gorgeous Red Rocks Amphitheatre was an absolute winner. The set kicks off with an enthusiastic version of the fan-favorite "The Stone," which spread into a crowd-sung clip of the Elvis Presley-chestnut "Can't Help Falling in Love," and then moved quickly into a hysterical version of the new song "American Baby," which Matthews handled without kid gloves. The band stamped "2005" on the recording, which featured "Time of the Season," the Zombies classic that the group covered regularly on its summer tour. Even though Matthews is in fine voice throughout the two discs, Carter Beauford is the single most dominating record on "Weekend on the Rocks." Matthews again proves to be one of the very best drummers that has been complemented with his compelling and powerful runs on such songs as "Say Goodbye" and "Halloween," that many fans still rank as the finest moment of the Red Rocks run.