In the spring of 1990, Tupac Shakur was shuttling between Marin City and Oakland, California, restlessly seeking his future. His manager, Atron Gregory, was shopping his demo tape but with little success so far. Meanwhile, activism beckoned. Friends of his mother, the former Black Panther revolutionary Afeni Shakur, had engaged Tupac to become the youth chairman of the New Afrikan Panthers, a youth division of a Black nationalist political group, with responsibilities across the country in Atlanta. This excerpt from the new Tupac Shakur: The Authorized Biography by Staci Robinson tells the story of when Tupac’s Bay Area friend and supporter Leila Steinberg, realizing that Tupac needed a musical path forward to keep him from heading east, sounded the alarm.
When Leila called Atron to let him know that Tupac’s focus was being redirected, he called Shock G right away. A rapper and producer, Shock was one of the masterminds behind the group Digital Underground, which had already made waves with the release a few months earlier of their debut album Sex Packets. Before Atron had signed Tupac, he had asked Shock to check him out first. Convinced by the young man’s talent, Shock had agreed to help put together Tupac’s demo. When Atron called, Shock was making preparations to continue the domestic leg of the Digital Underground’s tour before the group headed to Japan.
“Can you do something with Tupac?” Atron asked.
Shock was confused. “What do you mean?”
“Can you take him on the tour with you?”
“What? We’re full.”
“Well, if we don’t do something, we’re gonna lose him.”
“Maybe I can replace one of the roadies?” Shock offered.
That would have to do. But first Shock made sure to sit Tupac down and explain a roadie’s responsibilities. He cautioned him that they included menial tasks such as carrying bags for the artists. He told Tupac that he didn’t want to humiliate him by asking or expecting him to do this on tour — Shock understood that Tupac, too, was an artist, not a bag handler. Tupac was quick to say he didn’t care. “I’ll do anything. I’m goin’ crazy here.” So Shock pulled DU member Money-B’s brother off the tour and gave Tupac his spot. The way Shock figured it, Money’s brother wasn’t a rapper, but Tupac was. If it came to it, Tupac could serve as a backup dancer and even rap in a pinch. But mostly it was about offering him the promise of something more.
“Tupac was not going to wait for anybody,” recalled Atron. “He was frustrated because he wanted to get out there and show his talents and do what everyone else was doing. If not, he was gonna leave and go somewhere else.”
The Big Daddy Kane: Chocolate City tour was scheduled to roll through more than twenty cities in two months. Kane, with his catchy rhymes and sharp fashion, had become a breakout star with his albums Long Live the Kane and It’s a Big Daddy Thing. Along with Digital Underground, his supporting acts on the tour included Queen Latifah, who had just scored her debut hit single, “Ladies First”; rapper MC Lyte; and 3rd Bass. Eric B. & Rakim and De La Soul would also join the lineup in cities along the way, as would an up-and-coming artist named Jay-Z.
As Shock and crew took off on a cross-country flight to Georgia, where they’d start the bus leg of the tour, a new chapter of Tupac’s journey began. He was embarking on a life onstage, a goal he’d dreamed of since the curtain opened at his first acting performance in Lorraine Hansberry’s A Raisin in the Sun, only five years earlier. But when the group arrived at the first venue, in Augusta, it became apparent that Tupac would not be humbled by the opportunity. There would be no hanging back to watch, no playing it cool to get the lay of the land. He was a man on a mission, outspoken, in your face, righting wrongs wherever he saw them — even if it meant mixing it up with the tour’s one and only sound man.
During Digital Underground’s set, static and feedback interrupted the volume levels of the microphones. According to Tupac, it ruined their performance. By the time the set ended, he was fuming. As the group walked backstage, Tupac ran over to the sound man and yelled, “You fucked up our sound! And you did that shit on purpose!”
“Pac tried to knock his head off,” Money-B remembered. “He swung at him. I mean, the sound man did actually do something that was way out of line, and everybody really did wanna kick his ass, but Pac was ready to jump on him.” When Money told him to calm down, Tupac grew even more infuriated.
But Tupac was also giving others, including Atron and Shock G, reasons to tell him to calm down. He was always the first to react, ready to challenge any security guard or police officer. They spent many evenings trying to control Tupac’s energy and unpredictability. By the end of the tour, telling Tupac to calm down had become a running joke.
During daily meetings on the tour bus, Tupac was always perched and ready to inject a comment, amend the agenda, or just add his two cents. And after Tupac proved he could carry bags and fulfill his roadie tasks, Shock G asked him to come onstage with the rest of the group to perform as one of the backup dancers.
The Digital Underground set was not your average hip-hop show. The group rapped and they danced, but it was the props and theatrical antics that made them one of the most memorable musical acts of the ’90s. Shock G was the quintessential front man, seamlessly moving in and out of character as his alter ego, Humpty Hump, and hyping up the crowd with water guns and blow-up sex dolls until the audience was in a frenzy. Tupac dove in, headfirst, ready to be part of it all.
The moment he stepped onto the stage as a backup dancer, his confidence and charm caught the attention of the female fans in the audience. “Pac was immediately hot with the ladies from city one,” Shock recalled. “That’s when we really knew he was a star. We were already working on his albums. We believed in him. We knew he could rhyme. But we knew he was a star by how the girls reacted.” Even before the first show, during soundcheck, Tupac ended up in the back of the bus with a girl he’d just met that day. Money-B was astounded. “I was thinkin’, How’s this dude gonna come here the very first day and get chicks before me?
The girl and Tupac created a potentially explosive situation when the bus driver noticed a strange man chasing the bus as it pulled away from the arena. The driver came to a stop and opened up the doors. “Is my girl on there?” the man demanded, evidently a disgruntled boyfriend. A sea of no’s answered loudly from the bus. The bus driver shut the door, leaving the man standing there while she and Tupac hid in the back.
When Shock noticed the adoring response Tupac received from female fans during the show, he decided to give him a shot on the microphone. At first, Tupac freestyled, but that posed a problem; Tupac couldn’t contain himself to just one verse here or there. He instantly started to take over other members’ verses by rapping it with them, or for them. Sometimes, when one of the singers was hitting a chorus and Tupac didn’t like the way it sounded, he would even try to sing over it to keep the audience focused on him. “He would just take the whole show in his hands,” Shock recalled. “I kept feelin’ like Frank in Scarface, and he was Tony Montana. He was just tryin’ to flip the whole script.”
Shock asked him to chill. Tupac ignored him. Shock warned him again. But Tupac didn’t care whose turn it was. He didn’t care if he was hired initially just as a roadie. Every time Shock put the mic in his hand, Tupac was on a mission.
After a few warnings, and another night of Tupac stepping on someone else’s verse, Shock had had enough. He fired Tupac. “You’re not a singer, Pac,” he explained.
“But he wasn’t singing that shit right,” Tupac protested. “You wouldn’t know. You’re not a singer.”
“But we were losin’ the crowd. They weren’t likin’ that shit. I had to do somethin’ to get everyone back into it.”
“How would you like it if someone sang over your parts?” Shock asked.
Tupac cut to the chase. “Fuck that! What? You sending me home?” “Yeah, I’m sending you home,” Shock fired back. Then he yelled loudly to everyone who could hear, “Fuck that! Yeah, Pac’s off the tour!”
But he never went. Instead of accepting that he was fired and leaving that night, Tupac ended up in the lobby congregating with the crew. Shock sat at the piano, with everyone gathered around, freestyling and singing, unwinding from a long day. And there was Tupac rollin’ right along like nothing happened. Like he hadn’t been fired. Like he wasn’t supposed to have found his own way home and be halfway there by now. He couldn’t help himself. He loved his new life and he especially loved the after-show freestylin’ sessions. MC Serch from 3rd Bass was always there, and sometimes Queen Latifah. “Anytime he had a chance to speak out, and that would be in those freestyle sessions, he did. Tupac would wanna go all night,” recalls Money-B.
And so it went, Shock kicking Tupac off the tour, Tupac refusing to go. Shock laughed about it years later. “I used to send Pac home a lot. We’d curse each other out, but two hours later we’d get over it.” Looking back, he summed up his relationship with Tupac by saying, “It was one long argument.”
AS DIGITAL UNDERGROUND’S “Humpty Dance” hit number 1 on Billboard’s rap singles chart, the group’s stock increased and opportunities abounded. One of these opportunities was an invitation to go back on the road, this time with some of Tupac’s biggest hip-hop heroes — the politically charged rap group Public Enemy, led by Flavor Flav and Chuck D. Just two years before, Tupac had skipped school and rushed to meet Flavor Flav at the local radio station, just hoping to get a photo; now he was part of a lineup that would travel across the country with Public Enemy as they promoted their new album Fear of a Black Planet. Heavy D, Ice Cube, and Queen Latifah would also join parts of the tour.
The buses for the Fear of a Black Planet tour offered artists a more luxurious experience — bigger beds and kitchen areas and better TVs — than those for Big Daddy Kane’s tour, but what mattered most to Tupac was who was on the bus. Even though it was expected that each group and their entourage remain on their assigned bus during their travels, Tupac roamed freely, often forming friendships with girls who were part of the adjoining entourages.
One of them was 25-year-old Rosie Perez, a dancer in Heavy D’s act, and at the beginning of a career that would, like Tupac’s, take her far in Hollywood. Enamored and curious, she remembered the first time she saw Tupac. Standing with Heavy D when Tupac took the stage, she was taken by his presence. “That muthafucka is a star!” she yelled out. “And everyone just started to look at him, because I said it, I said it really loud. We were in the wings. And I remember walking out of the wings of the stage down into the front, where security is, so I could watch him. I don’t know why I did that; he just compelled me to do so. That was just his greatness.”
Once the two got acquainted they realized they shared similar backgrounds. After that, they often found themselves sitting next to each other as the buses rolled through the countryside. At one stop on the tour, Tupac asked if he could recite a poem for her. When he was done, Rosie said, “Yo, that’s good. You’re going to write a book of poetry.”
Tupac responded, “I’m going to be bigger than a book.”
Despite the excitement of being on another nationwide tour, there were still moments when Tupac’s troubled family life weighed heavy on his heart. Periodic calls to New York to talk to his sister, Sekyiwa and check in on how Afeni was holding up in Marin City left him uncertain. He knew his mother had a long road ahead of her in beating her drug addiction, but he held on to his hope, believing that she was strong enough to find a path to recovery. Sometimes during these sad and discouraging moments, he would sit alone in his hotel room listening to Mariah Carey’s “Vision of Love”:
Felt so alone
Suffered from alienation in Baltimore and Marin City, Tupac’s reaction became reflexive, the intensity never easing.
When Digital Underground performed at venues in the Bible Belt states, their stage show had to be revised because local laws forbade “crude” acts — a designation that certainly included the humping and dancing with blow-up dolls that had become one of the group’s performance signatures. Instead of leaving out the props, though, the band devised a plan. They would frolic with the dolls as usual, but as soon as the show ended, instead of going backstage where the officers would be waiting, they would jump off the five-foot stage and land in the audience. From there, they could blend in with the crowd, and the police officers who lined the stage wouldn’t be able to find them.
One night, as soon as the show ended, Shock jumped into the audience first, followed by Tupac and Money. While Shock and Money mixed calmly with the fans, ensuring that no attention was brought to them, Tupac sprinted through the audience toward the parking lot. When Money finally made his way outside, he spotted Tupac darting around and hiding behind cars. “He was ducking behind cars like he was on Mission: Impossible or something,” Money-B recalled with amusement. In the end, this paranoid, over-the-top behavior made him an obvious suspect to the cops who had rushed outside, leading to his eventual arrest and a night in jail for public misconduct.
As much as Tupac detested security guards and police officers, he was not above doing some policing himself, taking matters into his own hands if those he cared for were wronged. In Oklahoma City, news traveled backstage that someone had entered Public Enemy’s dressing room and stolen Chuck D’s signature black leather jacket. Tupac was infuriated, another holdover response from Afeni’s lessons about lying and stealing. He combed the place looking for the culprit. “I think I know who did it. I’m gonna find out who did it,” Tupac promised Chuck D.
Hours later, while everyone gathered in the hotel lobby to board the bus, a man suddenly barreled through the sliding-glass doors. Tupac was in hot pursuit, catching up quickly enough to land a few punches before the man jumped behind the reception desk. No one quite understood what was happening. Tupac scrambled to get to the man behind the desk, but someone on the tour restrained him. In that moment, the thief was able to jump back over the desk and escape.
“Why you holdin’ me, man?!” Tupac yelled. “I found the guy! That’s the guy that stole Chuck D’s jacket. Let me go!” By then it was too late. Although it seemed that Tupac was the only one who truly cared about the petty theft, he still earned respect for his efforts. “He created his own legend within that first tour,” Money-B remembered, “where every group and band that was with us went away wondering what was going to happen, what we were going to do with him. But they knew they were gonna see him again.”
Adapted from the book TUPAC SHAKUR: The Authorized Biography by Staci Robinson. Copyright © 2023 by Amaru Entertainment, Inc.. Published in the United States by Crown, an imprint of Crown Publishing Group, a division of Penguin Random House LLC. All rights reserved.