Which rappers best withstood time and why?

A Note from James

Tupac Shakur—one of the greatest rap artists ever—was shot and killed almost two decades ago. What else is there left to say about him? What new things can be said?

Well, Jeff Pearlman’s new book, Only God Can Judge Me: The Many Lives of Tupac Shakur, takes on that challenge. In our conversation, we talk about what Jeff uncovered in his research, why he wanted to write another Tupac book, and what made this one different.

But first, a little story. Back in the ’90s, I was running a company that built websites. Around 1997 or ’98, Tupac’s mom wanted to release a new album of his music and build a website around it. I went in to pitch the project—$90,000, which would’ve covered payroll for another month. I needed that deal.

So I show up, ready to impress. Tupac’s manager says, “Okay, here’s my computer. Show me what you’ve got.” And I realize—I’ve never used a Windows machine in my life. I’d only ever used Macs. I couldn’t even figure out how to turn it on.

I had a computer science degree. I was a software engineer. I’d been running this company for years. But in that moment, I had to admit: “I don’t know how to use this machine.” He laughed me out of the room. Literally.

That was the day I learned that even the smartest pitch can fall apart if you forget to check which operating system you’re using.

Anyway—what else is there to talk about with Tupac Shakur? Jeff Pearlman and I figured it out.

Episode Description

In this episode, James sits down with bestselling author and journalist Jeff Pearlman (The Last Folk Hero, Showtime, Sweetness) to talk about his latest book, Only God Can Judge Me: The Many Lives of Tupac Shakur.

Pearlman explores the contradictions, brilliance, and tragedy of Tupac’s life—how a performing arts kid from Baltimore became the poetic voice of West Coast hip hop, and how his complex identity was shaped by the Black Panther movement, celebrity culture, and the rise of gangsta rap.

James and Jeff unpack Tupac’s evolution from Digital Underground hype man to solo artist, his influence on music and film, and the deeper meaning behind songs like Brenda’s Got a Baby. They also trace the events leading up to his death, separating myth from reality, and reflect on what Tupac’s legacy might have become if he’d lived.

What You’ll Learn

• Why Tupac’s “gangster” persona was more performance than reality
• How his upbringing under a Black Panther mother shaped his worldview
• The untold story behind Brenda’s Got a Baby—and how Pearlman found the real “baby” years later
• The truth about Tupac’s relationship with Biggie Smalls and the events that led to both of their deaths
• Why Tupac might have gone on to become a political or cultural leader, not just a rapper
• How hip hop evolved from the storytelling of the ’90s to today’s more fragmented sound

Timestamped Chapters

• [00:00] Introduction – James shares his connection to Tupac’s world
• [02:43] A Note from James – The web pitch that went wrong
• [05:00] Why Jeff Pearlman wrote a Tupac book
• [07:00] The challenge of writing outside his comfort zone
• [09:00] Tupac’s background and the myth of the “gangsta” image
• [11:00] The evolution of rap from the ’80s to now
• [16:00] What made Tupac’s art different from his peers
• [18:30] Tupac as a natural actor—and how he almost won an Oscar
• [21:00] Was his “gangster” side authentic or performance?
• [23:30] The night Tupac was killed—what really happened
• [26:00] How the East Coast–West Coast rivalry became fatal
• [30:00] The origin of Brenda’s Got a Baby and the real-life people behind it
• [35:00] Tupac’s literal storytelling and emotional honesty
• [36:30] How he might have evolved as an artist—or politician
• [38:00] The conversation that inspired a future Newark city councilman
• [40:00] Hip hop’s intelligence, legacy, and misunderstood brilliance
• [45:00] From Ice-T to Death Row: how labels, power, and politics shaped the scene
• [49:00] Wrapping up with gratitude—and a little hair envy

Additional Resources

• Jeff Pearlman – Only God Can Judge Me: The Many Lives of Tupac Shakur
• Jeff Pearlman’s Official Website
• Tupac Shakur – Brenda’s Got a Baby (Official Video)
• Digital Underground – Same Song (Tupac’s first verse)
• FBI Case File: Death of Tupac Shakur
• Film: Juice (1992), starring Tupac Shakur and Omar Epps

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