The name refers to the Underground Railroad, the secret network through which enslaved people escaped from the South to the North in the 19th century. For Tupac it was a self-description: a group of young musicians helping each other along. It was not a fixed band but a collective from the Digital Underground circle in the Bay Area.
Who was part of it
According to common accounts, the Underground Railroad included Raw Fusion (the side project of Money-B and DJ Fuze), Live Squad with Tupac’s friend Stretch, producer Big D the Impossible, Pee-Wee, Jeremy “J-Z” Jackson, and several members of Digital Underground around Shock G. The credits of 2Pacalypse Now largely confirm this circle, naming Big D the Impossible, Shock G, Pee-Wee, Jeremy “J-Z” Jackson, Raw Fusion and Live Squad as producers. Even so, there is no definitive membership list, the collective was open and changed over time.
The first recordings
From 1990 onwards, this circle produced Tupac’s first solo tracks; Shock G and Atron Gregory shopped a demo to labels that included the future single Trapped. The traces can be heard in his early guest spots: in 1991 he rapped on Raw Fusion’s #1 with a Bullet, in 1992 on Pass the 40 with Raw Fusion, Saafir, Stretch, Pee-Wee and others.
Above all, it is where his debut album 2Pacalypse Now was made, recorded at Starlight Sound in Richmond and released by TNT Recordings and Interscope on November 12, 1991. The Underground Railroad is credited as the production team; Shock G co-produced, along with musicians from the Digital Underground orbit. The album, with songs like Brenda’s Got a Baby and Trapped, was fiercely attacked for its criticism of the police (see Dan Quayle).
The end
According to common accounts, the collective broke up after about two years. That fits the timeline: from 1992 Tupac became known as an actor (Juice) and solo artist, worked more and more in Los Angeles and New York, and formed Thug Life with Stretch and Big Syke in 1992-93. The Underground Railroad remains the workshop where his first album was built.