Between the release of his first album, and the second one five years later, D'Angelo made guest appearances on various different soundtracks, including Belly, a 1998 film. He also appeared on The Miseducation of Lauryn Hill album where he sang the song "Nothing Even Matters". D'Angelo's second album, Voodoo, was finally released in 2000. It debuted at number one and went on to win two awards at the Grammys.

He was arrested in 2005, and later charged with possession of marijuana, possession of a controlled substance and driving while intoxicated. He plead guilty to DUI and the marijuana charge. On April 13, he was a fined and given a suspended sentence. His driver's license was also revoked. On September 12, of that same year, he received a three-year suspended sentence on the cocaine possession charge.

A week after he was sentenced on the cocaine possession charge D'Angelo was involved in an accident and was critically wounded. In August, 2007, D'Angelo was finally sent to court for the accident in 2005. His charges included reckless driving and driving with a suspended license. He then plead guilty to the charges and was ordered by the court to pay $1,250 fine. He also forfeited his license for 15 months and received a nine-month jail sentence that was suspended. After the proceedings he revealed that a new album was in the works.

• 1995: Brown Sugar
• 1998: Live at the Jazz Cafe
• 2000: Voodoo