In the late eighties, Shakur teamed up with Humpty-Hump (a.k.a. Eddie Humphrey, a.k.a. Gregory "Shock-G" Jacobs) and other Oakland-based rappers to create Digital Underground, a band intent on massive bass beats and frenetic, Parliament-Funkadelic-style rhythms. In 1990, the group released its debut and best album, Sex Packets, a pulsating testament to the boogie power of hip-hop, featuring two classic tracks, "Humpty Dance" and "Doowutchyalike." After an EP of re-mixes in 1991, D.U. released Sons of the P and, the following year, The Body- Hat Syndrome, all on Tommy Boy Records.
In 1992, Shakur entered a most fruitful five-year period. He broke free of D.U. and made his solo debut, 2Pacalypse Now, a gangsta rap document that put him in the notorious, high-speed lane to stardom. That same year he starred in Juice, an acclaimed low-budget film about gangs which saw some Hollywood success. In 1993, he recorded and released Strictly 4 My N.I.G.G.A.Z., an album that found Shakur crossing over to the pop charts. Unfortunately, he also found himself on police blotters, when allegations of a violent attack on an off-duty police officer and sexual misconduct arose. The same year, Shakur played a single father and Janet Jackson's love interest in the John Singleton film Poetic Justice.
In November of 1994, he was shot five times during a robbery in which thieves made off with $40,000 worth of his jewelry. Shakur miraculously recovered from his injuries to produce his most impressive artistic accomplishments, including 1995's Me Against the World, which sold two million copies, and the double-CD All Eyez on Me, which sold nearly three million. As his career arc began a steep rise toward fame and fortune, Shakur was shot (most say suspiciously) and killed after watching a Mike Tyson fight with Death Row Records president Marion "Suge" Knight. Though his death was a jolt to his fans and the music community, Shakur himself often said that he expected he'd die by the sword before he reached thirty.
Following his passing, Shakur's label released an album, The Don Killuminati, under the pseudonym "Makaveli." The cover depicted Shakur nailed to a cross under a crown of thorns, with a map of the country's major gang areas superimposed on it. In January of 1997, Gramercy pictures released Gridlock'd, a film in which Shakur played the role of a drug addict to mostly good reviews. His final film, Gang Related, was released in 1997, and Death Row is said to have several unreleased recordings in the vaults for potential future release.