WHY LISTEN? Because Jeff Pearlman strips away the myth to reveal the real Tupac Shakur—a brilliant, wounded, and fiercely human artist whose story still speaks to America’s struggles with family, race, trauma, and truth.

Happy Halloween, everyone. To celebrate, we’re turning our attention to one of white America’s most mythic—and most feared—figures: the hip-hop legend Tupac Shakur. In Only God Can Judge Me, his new Tupac biography, the Los Angeles-based sportswriter Jeff Pearlman reveals both the humanity and the heartbreak behind the myth. Yes, Pearlman concedes, Tupac Shakur was far from perfect. Yet in his music, his movies, and above all his short, turbulent life, Tupac embodied the quintessential American hero—a man who, despite all the injustice and chaos around him, stood up for what was right. Here was someone whom perhaps not even God could judge.

1. Tupac’s story is fundamentally about trauma, not violencePearlman’s biggest revelation wasn’t about gang culture or rap feuds—it was about the crushing weight of intergenerational trauma. Watching his hero mother, former Black Panther Afeni Shakur, descend into crack addiction left Tupac with wounds that shaped everything. “The trauma of having your hero become this thing that’s unrecognizable and zombie-like,” Pearlman explains, is what people miss when they romanticize Afeni as simply a “goddess” or reduce Tupac to a “son of a Black Panther.”

2. Tupac was a theater kid before he was a gangster rapperBefore Marin City’s crack epidemic and Death Row Records, Tupac Shakur was studying at the Baltimore School of the Arts—writing poetry, dancing, and dreaming of acting. He was “this free spirit who lived this beautiful, beautiful life,” Pearlman says. That artistic foundation—not the tough-guy persona—was his authentic self. Actor Jim Belushi told Pearlman that Tupac was on the verge of becoming an Academy Award–winning actor. The gangster image that Death Row demanded wasn’t who he wanted to be.

3. The book is sad—and that surprised everyone, including Pearlman“I didn’t expect this to be a sad book,” Pearlman admits. But every proofreader who read it said the same thing: “God, this book is so sad.” Tupac died young, nearly broke, used by powerful people, and alone in many ways—desperate to be understood and accepted. “Life kind of gobbled him up,” Pearlman says. The mythology of Tupac as an invincible icon obscures the heartbreaking reality of a 25-year-old carrying impossible weight.

4. Writing about Tupac as a white suburban sportswriter required radical humilityPearlman acknowledges the cultural distance he had to cross: “It’s a weird situation being a white guy who grew up in middle-class rural America writing about Tupac... I never experienced that level of trauma.” His approach wasn’t to claim expertise but to listen deeply and interview exhaustively. Along the way, he gained an unexpected education in Southern California gang culture—discovering that many former gang members and drug dealers “are wonderful guys” who “just had different journeys.”

5. Tupac would be “absolutely furious” about Trump’s America—and probably arrestedWhen asked what Tupac would think of today’s political climate, Pearlman doesn’t hesitate: “I think 25-year-old Tupac would be horrified, but not surprised.” More specifically, “I can’t imagine Tupac Shakur of any age just sitting back” while ICE agents grab people in unmarked vehicles. “I think he’d be 100% getting arrested at ICE roundups,” Pearlman says. As for Biden or Harris? Tupac would probably see them as “corporate shills who don’t stand up enough for the people.”

Keen On America is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit keenon.substack.com/subscribe

221: Special Guest Stephen Embry - Meta Spectacles 👓 Approved AI, and the Best Bathroom Breaks on a Plane 🚽

In the News

Outro

The AI-powered Podcast Player