Life on Death Row Records

Image of Shakur, Snoop "Doggy" Dogg, and Suge Knight during Shakur's tenure on Death Row (1995)

Upon his release from Clinton Correctional Facility, Shakur immediately went back to song recording. He began a new group called Outlaw Immortalz. Shakur began recording his first album with Death Row and released the single "California Love" soon after.

On February 13, 1996, Shakur released his fourth solo album, All Eyez on Me. This double album was the first and second of his three-album commitment to Death Row Records. It sold over nine million copies. The record was a general departure from the introspective subject matter of Me Against the World, being more oriented toward a thug and gangsta mentality. Shakur continued his recordings despite increasing problems at the Death Row label. Dr. Dre left his post as house producer to form his own label, Aftermath. Shakur continued to produce hundreds of tracks during his time at Death Row, most of which would be released on posthumous albums such as Still I Rise, Until the End of Time, Better Dayz and Pac's Life. He also began the process of recording an album with the Boot Camp Clik and their label Duck Down Records, both New York-based, entitled One Nation.

On June 4, 1996, he and Outlawz released the diss track "Hit 'Em Up", a scathing lyrical assault on Biggie and others associated with him. In the track, Shakur claimed to have had intercourse with Faith Evans, Biggie's wife at the time, and attacks Bad Boy's street credibility. Though no hard evidence suggests so, Shakur was convinced that some members associated with Bad Boy had known about the shooting beforehand due to their behavior that night and what his sources told him. Shakur aligned himself with Suge, Death Row's CEO, who was already bitter toward Combs and his successful Bad Boy label; this added fuel to building an East Coast-West Coast conflict. Both sides remained bitter enemies until Shakur's death.

On July 4, 1996, he performed live at the House of Blues with Outlawz, Tha Dogg Pound, and Snoop "Doggy" Dogg also headlining. This was Shakur's very last live performance.

While incarcerated in Clinton Correctional Facility, Shakur read and studied Niccolò Machiavelli and other published works, which inspired his pseudonym "Makaveli" under which he released the record album The Don Killuminati: The 7 Day Theory. The album presents a stark contrast to previous works. Throughout the album, Shakur continues to focus on the themes of pain and aggression, making this album one of the emotionally darker works of his career. Shakur wrote and recorded all the lyrics in only three days and the production took another four days, combining for a total of seven days to complete the album (hence the name). The album was completely finished before Shakur died and Shakur had complete creative input on the album from the name of the album to the cover, which Shakur chose to symbolize how the media had crucified him. The record debuted at number one and sold 663,000 copies in the first week. Shakur had plans of starting Makaveli Records which would have included Outlawz, Wu-Tang Clan, Big Daddy Kane, Big Syke, and Gang Starr.