Before Thug Life, before Death Row, the East Coast–West Coast beef, before Makaveli, before he went down as one of the most iconic rappers of all time, Tupac Shakur was a roadie and backup dancer, making his way through the Oakland hip hop scene with Digital Underground.
The group’s frontman, the late Shock G, met and took a liking to Pac, giving him his first shot in show business during the early ’90s. Pac made his first rapping appearance on the group’s 1991 release, This Is an EP Release, on “Same Song” and also appeared in the video.
Not long afterwards, 2Pac would sign his own recording deal with Interscope Records and drop his debut album, 2Pacalypse Now, in November 1991. The album was a significant departure from Digital Underground’s fun loving, funky style; instead focusing on social-political issues.
Digital Underground would still play a big part in Pac’s pre-Death Row career; with Shock G producing his 1993 hit single “I Get Around” and appearing on “Fuck the World” off 1995’s Me Against the World.
In a 2017 interview with Rolling Stone, Shock G recalled what it was like having Tupac in the studio:
Shock G: Outside of working with him, I didn’t see him much. I saw him every time I was in the studio with him – and even then didn’t see him much. Cause he would just pace, and he’d come back in the room. “Is the beat ready yet? Goddamn.” Restless. He’d go outside and smoke. Go across town or something. He’d come back. “Yo, can I rhyme? Can I rhyme?” Unlike most artists who want to sit there as we figured out where the string line is going, he didn’t sit for each listen. He would come back out of the booth and listen one time down. Once we started selecting reverbs and levels and all that, he would get bored and just tap me on the shoulder and say, “Alright, make that shit dope.”I Get Around: The Oral History of 2Pac’s Digital Underground Years | Rolling Stone