Tupac Shakur allegedly wore a cheerleader’s skirt with pom-poms and kissed boys at parties during his high school years at a Baltimore arts school, according to a new biography that explores the late Hip-Hop icon’s life in detail.
Author Jeff Pearlman, known for his deep-dive biographies, interviewed nearly 700 people for his upcoming book Only God Can Judge Me: The Many Lives of Tupac Shakur.
The book draws from years of research and hundreds of new interviews, including rare insights from Tupac Shakur’s sister, Sekyiwa.
Pearlman’s reporting uncovers a lesser-known version of Tupac Shakur —one shaped by theater, experimentation and artistic freedom at the Baltimore School for the Arts.
Among the revelations is that the real-life “Brenda” from his song “Brenda’s Got a Baby” actually had a child, a detail previously unknown to the public.
Another is Shakur’s expressive fashion and openness during his teen years.
“People who knew Tupac in high school love the way he dressed, especially at the Baltimore School for the Arts,” Jeff Pearlman told AllHipHop. “He would show up with nail polish on his fingers. He had a peroxide yellow strip, running through his hair. He spray-painted on his jeans. And he would show up most days drinking water out of a baby bottle. He was just really eccentric and artsy.”
Former classmates described Shakur as bold and uninhibited, often pushing boundaries in both style and behavior. During Spirit Week in 1988, he walked through the cafeteria in a full red, white and blue cheerleader uniform—skirt, shoes and pom-poms included.
“I asked around—’excuse me, who is this crazy boy?’” classmate La Donna Bonner recalled. “‘And what has he been smoking?’”
Tatiana Bliss, another peer, remembered Shakur as one of the few boys wearing pink eyeshadow, black nail polish and bleach in his hair. His look was shaped by necessity and creativity, often spray-painting his own clothes due to financial hardship.
One of Shakur’s closest friends at the school was Seth Bloom, a gay theater student from suburban Baltimore. Bloom recalled their friendship as intense and experimental, noting the school’s sexually open environment.
“It was a pretty f###### horny school,” Bloom said. “We were artistic and experimental.”
At a class party, Bloom said Shakur kissed him during a game of truth or dare.
“So he did,” Bloom recalled. “He kissed me. We kind of vamped it up, our lips touched. I know I wasn’t the only boy Tupac kissed. When we were alone I always felt a thing. You know that sexual tension where you hold a glare a second or two too long, or you touch someone longer than normal? That was Tupac. My belief is he was somewhere between heterosexual and bisexual.”
Pearlman doesn’t see Shakur’s sexual exploration as controversial.
“As for his sexuality, I would say there was some experimentation at the school for the arts,” he told AllHipHop. “Anyone who makes it a big deal or thinks it’s some type of indictment of his character is being an idiot. He was an artsy kid surrounded by artsy kids. It wasn’t a big deal then, and it certainly shouldn’t be a big deal now.”
Pearlman emphasized that while some readers may focus on these revelations, they are only a small part of a much larger story. “I know people like gossip and innuendo about the stuff, but to me, it’s one of the least interesting parts of his fascinating life,” he said.
The book also delves into Shakur’s ability to adapt to different environments, a skill that began in Baltimore and continued to evolve when he moved to Northern California. His ability to shift his persona depending on where he was and who he was with became a defining trait throughout his life.
Pearlman’s biography aims to present a fuller picture of Shakur beyond his public image as a defiant Hip-Hop icon.
It portrays a young man shaped by poverty, creativity and personal contradictions. The book also includes stories never before made public, offering a deeper understanding of the man behind the music.
Only God Can Judge Me: The Many Lives of Tupac Shakur was published on October 21.
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