In 2001, Gil Scott-Heron was sentenced to one to three years' imprisonment in New York State for possession of cocaine. While out of jail in 2002, he appeared on the Blazing Arrow album by Blackalicious. He was released on parole in 2003. On July 5, 2006, Scott-Heron was sentenced to two to four years in aNew York State prison for violating a plea deal on a drug-possession charge by leaving a drug rehabilitation center. Scott-Heron's sentence was to run until July 13, 2009. He was paroled on May 23, 2007. The reason given for the violation of his plea deal was that the clinic refused to supply Scott-Heron with HIV medication.
After his release, Scott-Heron began performing live again, starting with a show at SOB's in New York on September 13, 2007. On stage, he stated that he and his musicians were working on a new album and that he had resumed writing a book titled The Last Holiday, previously on long-term hiatus, about Stevie Wonder and his successful attempt to have the birthday of Martin Luther King Jr. declared a federally recognized holiday in the United States.
On October 10, 2007, the day before a scheduled (but ultimately cancelled) second SOBs performance, he was arrested on felony possession of cocaine charges. However, he has continued to make live appearances at various US venues during the course of 2008 and 2009, including further appearances at SOBs in New York. He has also stated in interviews that work is continuing on his new album, which will consist mainly of new versions of some of his classic songs plus some cover versions of other artists' work.