Matthews' older sister Anne, who lived in South Africa, was murdered by her husband in early 1994. Her husband subsequently died by suicide, on or around January 27 of that year. The event had a profound effect on Matthews' outlook on life and was referenced in a few of his songs. On January 29, 1994, he performed with Tim Reynolds at the Wetlands in New York, where he dedicated that performance "to her [Anne's] memory". Dave Matthews Band's Under the Table and Dreaming, released later that year, was dedicated to her. Anne Matthews was survived by her two children and they traveled to the United States following her death. Dave and his younger sister Jane (after whom the Dave Matthews Band song "The Song That Jane Likes" is named) took responsibility for the children's upbringing.
Matthews focused primarily on songwriting and performances with the Dave Matthews Band from 1990 to 2003. DMB is an artistic blend of acoustic guitar, bass, sax, drums and fiddle music. In 1994, DMB signed with RCA Records. Since that period, he has occasionally ventured outside the band in various solo performances and records. Matthews sang on the track "Sing Along" on Blue Man Group's second album The Complex in 2003. Later that year he released a solo album, Some Devil, which went platinum; its single, "Gravedigger", won a Grammy Award in 2004. Dave Mathews drew motivation for this song from the long-running Monster Jam celebrity Grave Digger. To support the album, Matthews toured with a group of musicians (many of whom performed on "Some Devil") under the name Dave Matthews & Friends.