Signing to Island Records through A. Haqq Islam's University Records imprint, the group released two successful albums, Dru Hill and Enter the Dru, before separating for a period from late 1999 to 2002, during which time Sisqó and Woody released solo albums. Dru Hill was influenced by the Dragon and Asian culture, as displayed in their wardrobe and logo. While Woody's album, Soul Music, was a moderate success in the gospel music industry, Sisqó's debut album, Unleash the Dragon, and its hit singles, "Thong Song" and "Incomplete", were major pop successes, and established Sisqó as a household name outside of Dru Hill. Sisqó's second album, Return of Dragon, did not perform as well.


In 2002, by then part of the Def Soul record label, following a merger between Island, sister label Def Jam Recordings and Universal Music Group, the group reunited and added fifth member Scola to the lineup for their third album, Dru World Order; after that album underperformed the group met with Island Def Jam president L.A. Reid about a follow-up. When the group failed to develop their fourth album, Def Jam cited the group as non-productive and destructive, having dropped the group from Def Soul in 2004. In 2009, the group signed to Kedar Entertainment Group and released their fourth album, InDRUpendence Day, the following year, with new member Tao taking the place of the again departed Woody.