Episode 496: Jeff Pearlman Finds the Little Guys – Home of The Creative Nonfiction Podcast

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“So much misery. It is so much misery. It is so hard. It’s not natural, locking yourself in your room for three years to focus on one person is not mentally healthy. Leigh Montville, great, great writer, said to me years ago, he’s like, ‘It’s an unnatural thing. You spend two years in a hole to come out for two weeks, you know?’” — Jeff Pearlman, author of Only God Can Judge Me.

Today we have Jeff Pearlman (@jeff_pearlman) returning to the show to talk about his 11th book, his latest book, Only God Can Judge Me: The Many Lives of Tupac Shakur (Mariner Books). Jeff has made a career out of being a sports writer, so when I heard he had turned his biographical eye toward a hiphop icon from the 1990s, I was especially intrigued by how he would approach it. It’s the kind of book he could pursue after having proved himself ten times before, with a few of his books becoming coveted NYT bestsellers. He interviewed close to 700 people for the book … that’s how you do this. THAT is how it’s done.

So Jeff is back. The first time he was on, I think I annoyed him a bit with my questions on “craft.” He kind of bristled at the idea that it was a “craft,” which maybe he thought was too cute a word to put on it. To him, it’s fucking work. You make all the calls. Then you make more. You go to the locations. You knock on doors. You report, report, report. It has more to do with tenacity and rigor than art … so I made sure I steered clear of things that felt too crafty this time around.

Jeff is all over the place. By that I mean he’s got a YouTube presence with The Press Box Chronicles, a TikTok presence (@jeffpearlmanauthor) with more than 300,000 followers. He has a podcast, Two Writers Slinging Yang (still waiting for my invite), a political Substack called The Truth OC, and his writing/journalism Substack Yang Yang.

He’s a writer in his 50s and he’s tremendously nimble. He understands, even with his profile, that nobody is going to champion your book like you can. Honestly, we can all take a page out of his book and how he has embraced the ever-changing playbook for book promotion. I wonder if I should join TikTok and just do random reviews of things. Like, my printer paper, this deodorant, books, that apple tree … fuck around and find out.

In this conversation Jeff and I talk about:

Book promotion
Finding the little guys
How he handled another Tupac biography publishing during his research for this book
The misery of it all
Conversations he had with Jonathan Eig, the PP winning author of King: A Life
Jeff’s favorite “version” of Tupac
And hitting the “fuck-it” stage.

Jeff’s CNFin’ Snippets

“Number 1, you have 20 seconds to catch someone’s attention, at most. Number 2, I’m not even sure who’s buying books anymore. They are selling, but I’m not sure where. Number 3, it’s so social-media generated, like, so social media generated. It’s crazy. It’s so much harder than it used to be.”

“That’s 100 100,000,000%, people. I don’t understand how any biographer misses that one. To me, it’s the most obvious thing in the world. It really is. I preach that shit all the time. I wrote Showtime. Showtime became an HBO show that put my kids through college. Magic. Kareem and Pat Riley did not talk to me for that book, but you know who did? Every backup Wes Matthews and Billy Thompson and Mike Smreck. Those guys were in the same meetings at the same time as those guys. So find your little guys.”

“My dad was my closest friend by far. I dedicated the book to him. I wrote: ‘To Stanley Pearlman, the original G.’ He would have no idea what that means. I use a Tupac line. I said, ‘I can picture you in Heaven with a blunt and a brew.’ And my dad did not really drink beer, and he never smoked a blunt. He would like that.”

“So for me, I go through despair, anger … I read the book [the authorized biography of Tupac], highlight everything, write down names. Who do I need to talk to?And then I get in my fuck-it stage. My fuck-it stage is fuck it. I’m just gonna bust my ass and do even better. That’s what I tried to do. I’m not saying it is better. I tried.”

“I sounded like the whiniest little wuss of all time. But he’s like, ‘you’re getting paid good money to earn a PhD on Tupac.’ He’s like, ‘I was paid good money to earn a PhD on Martin Luther King, I would have done that for free.’ He’s like, ‘and you would do this for free, too.’ And I was like, Yeah, that’s actually good. It’s a good way of thinking of it, and that’s kind of what keeps me going.”