Jeff Pearlman Randy Faehnrich/Prolific Media Share on Facebook Share on X Share to Flipboard Send an Email Show additional share options Share on LinkedIn Share on Pinterest Share on Reddit Share on Tumblr Share on Whats App Print the Article Post a Comment Jeff Pearlman is a self-described "cranky, middle-aged sportswriter ... who's seen it all." He's really not that cranky, but the other parts are true. The 53-year-old (a checkmark for the "middle-aged" part) former Sports Illustrated writer is now the author of 11 books, so he has seen quite a bit, if not "it all." Much of what Pearlman has seen through his three decades in sports journalism is now being distilled down into 20-minute stories for his excellent YouTube series, Press Box Chronicles with Jeff Pearlman. Related Stories Business Top Creators' Shows Find Second Life Off YouTube Business How Hollywood Learned to Love Influencers Press Box Chronicles is a side hustle (a side-side hustle if you count Pearlman's TikTok), but it also contains some of the best sports-storytelling (this side of Netflix's Untold) since ESPN's 30 for 30 stormed the space. To get the story of Press Box Chronicles itself, The Hollywood Reporter went straight to the source. Read THR's Q&A with Pearlman: *** I wanted to talk to you about your YouTube series Press Box Chronicles with Jeff Pearlman, but this is also fortuitously timed to the release of your new book, Only God Can Judge Me: The Many Lives of Tupac Shakur. How's that press tour going for you? It's just all unnatural, because you spend up three years basically living in a hole, and then you come out of the hole for two weeks, then you go back in the hole. That's basically what book PR is. You spent three years putting everything you have into this project, and then you spew about it [and] spew about it. [Then] no one wants to talk to you about it again, and you just kind of move on. And that's basically your full-time job now, right? It is my full-time job. Yeah, yeah. You don't do any freelance for magazines or the web? I do some here and there every now and then, but not a ton. Yeah, the market is definitely dried up. I wish there were more, like it used to be. I mean, I'm 53, so not that long ago for me, like back in the '90s, early 2000s, there were just 8,000 glossy magazines paying like $3 and $4 a word. That was a good time. Were you a Tupac guy or a Notorious B.I.G. guy? I feel like we all had to pick. I never was a big Biggie - I mean, I think Biggie is very talented and was an excellent rapper, but I was always much more drawn to Tupac. Do you have a favorite Tupac song, and is it the same as what your favorite Tupac song was before you started on the book? No, my favorite song is "Shorty Wanna Be a Thug." It's on All Eyez and Me, and it became my favorite work in the book because it really is him as a storyteller. And like, I really grew to appreciate him as a storyteller. I know everyone is like, "Oh, was he fake? Was he just a phony?" He wasn't a phony. He was a storyteller. He looked around him. And there's this whole background to that. So I'd say before it was, "I Ain't Mad at Cha," which is almost like saying your favorite Beatles song is like, you know, "Hey Jude." Mine is probably a cop-out too. It's probably "To Live and Die in L.A.," which is just an awesome summer song. That's like the hip-hop version of - in a good way - "I Love L.A." by Randy Newman. What's your next book? It's a book nobody's gonna read. It's just a passion project. I always wanted to do a memoir about my first two-and-a-half years in journalism. I was the world's biggest fuckup. No, I really was. So I just thought, I've always been telling these stories, and my wife's always like, "Oh, it's a really good book." It's a vanity project, yeah? Is the cover photo gonna be you in a backwards Kangol hat? Because that might be your biggest fuckup from the early years. (Laughs.) I stand by that hat! You do a nice job on The Press Box Chronicles theming your hats to the story of the day. Do you buy any specifically for the YouTube series or is your personal collection just that extensive? No, it's like, even the shirts- so we will film like three episodes in a batch, three or four. And at the end of one episode, I'll be like, "Oh, let me go get a different shirt." Even the hats - every now and then they'll match the subject, but a lot of times, what I try to think is, what hat haven't I worn in an episode. At one point I'm gonna wear- I have in that closet, my son who is now in college, I have his Little League Baseball hat, and at some point I'm gonna wear that hat. Jeff Pearlman attends a Winning Time event Getty Images Press Box Chronicles just launched in February - what's your biggest episode so far? I didn't even want to do the show. My TikTok growth was pretty quick - inexplicably rapid. I have more than 300,000 followers and I just joined a year-and-a-half ago. Super weird. And this company called 3Point0 Labs reached out t