Jeff Pearlman is a self-described cranky, middle-aged sportswriter whos seen it all. Hes 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. Press Box Chronicles is a side hustle (a side-side hustle if you count Pearlmans TikTok), but it also contains some of the best sports-storytelling (this side of Netflixs Untold) since ESPNs 30 for 30 stormed the space. To get the story of Press Box Chronicles itself, The Hollywood Reporter went straight to the source.

Read THRs QA 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. Hows that press tour going for you?

Its 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. Thats 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 thats basically your full-time job now, right?

It is my full-time job. Yeah, yeah.

You dont 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, Im 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. Its 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 wasnt a phony. He was a storyteller. He looked around him. And theres this whole background to that. So Id say before it was, I Aint 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. Its probably To Live and Die in L.A., which is just an awesome summer song.

Thats like the hip-hop version of in a good way I Love L.A. by Randy Newman.

Whats your next book?

Its a book nobodys gonna read. Its just a passion project. I always wanted to do a memoir about my first two-and-a-half years in journalism. I was the worlds biggest fuckup. No, I really was. So I just thought, Ive always been telling these stories, and my wifes always like, Oh, its a really good book. Its 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, its like, even the shirts so we will film like three episodes in a batch, three or four. And at the end of one episode, Ill be like, Oh, let me go get a different shirt. Even the hats every now and then theyll match the subject, but a lot of times, what I try to think is, what hat havent I worn in an episode. At one point Im 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 Im gonna wear that hat.

Jeff Pearlman attends a Winning Time event Getty Images Press Box Chronicles just launched in February whats your biggest episode so far?

I didnt 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 to me and they were like, Have you ever thought about doing a YouTube series where you tell a story? And I was like, Nobody wants to watch a 50-year-old sportswriter. And theyre like, No, Im telling you. Im telling you. And I was like, I mean, it sounds kind of fun, so Ill do kit, yeah.

It was growing OK, and then I did an episode on the this is the weirdest thing the 1984 San Diego Padres. That one became my biggest by far. I dont know why. I cant even understand why that one blew up, but its been, like, this kind of steady growth since. Every now and then some of them do particularly well; theres no rhyme or reason to me.

You have merch now, which is sort of the trajectory of monetization for these types of series have you considered doing live shows? Are you being pushed to do them?

They are, actually. Its kind of funny. They want to do shows where I travel around, like, do shows in different locations. And Im like, Nobodys gonna want to come and see me. I swear Ive said that 17 times, Nobodys gonna want to come and see me. Like, why would you? And theyre like, No, youre wrong. Im telling you youre wrong. Im not as reluctant as I used to be because I was wrong about the show as a whole, maybe Im wrong about this too. I dont know. But, I mean, look, if they want me to go to whatever, Tampa, Fla., or Toledo, Ohio, and talk sports, and I dont know sure, I mean, I would do it.

What about sponsors?

Oh, we recently have gained sponsors. Its interesting because I think would have had sponsors quicker, but I told [producers] very early on that I wont do anything with gambling. Its easier in the sports space right now to get gambling, [but] Im so horrified by what online gambling is doing to sports. The people putting on the show truly have been very supportive, and as soon as I said that, they were like, Dont worry. Im sure it wasnt their first choice, not booking gambling ads. So were sponsored by a card-collection company and a protein powder.

When you say youre horrified about what online gambling has done to sports, what do you mean exactly?

Number one, the number of kids now who are gambling in sports on their phones is preposterous, and you know, these companies dont give a shit about it. They dont care theyre happy about it. Just like when cigarette companies would say, We dont want kids smoking, but wink, wink were OK with it. Same thing.

I saw LeBron James doing an ad for DraftKings the other day do you really need the money this badly? Like, do you really need the money? Im not nearly, nearly, nearly nearly I dont have one/one-millionth the wealth of LeBron James, right? I just dont need the money that badly that Im gonna, like, start promoting gambling.

Press Box Chronicles has a bit more than 37,000 subscribers on YouTube. Is it close to surpassing book-writing as your primary form of income?

(Laughs.) No! No, not even close. Not even close. No, its not even close. Not even in the same ballpark.

The one thing thats cool is that I make money from TikTok.

I gotta get on TikTok.

TikTok is the best. Its been a career revival. I only got on because so, in February 2024, a bunch of layoffs happened in journalism. I went on Twitter Im not on Twitter anymore, but I went on Twitter and I kind of offered some advice to young journalists, where I was like This is what I would do. And theres a website called The Defector it used to be Deadspin, basically its everyone from Deadspin at The Defector. And the editor of The Defector is a guy named Tom Ley [he] ripped me in a column. The thrust of it was like, Why would you ever get social media advice from this old man? That was basically how I read it, right? It just lit a fire in me a little.

Im not joking about [this] thanks to that guy from Defector.

I was bothered by HBO changing the name of your book Showtime to Winning Time for the TV show, just to not have a show with the same title as a premium-cable competitor.

I mean, it did. I got over it very quickly. Like, I did get over it very quickly. I dont know. You know, like, Ive had titles for my books that I thought were perfect, and the publishers like, Were not going with that. Id be really upset, and then I came to realize that the titles had almost no impact on the success or failure of the book.

At first, I mean, I kind of got it, because theres a network called Showtime, so they didnt want to have a Showtime TV show. I wasnt thrilled, but I didnt ruin my day or anything.