The New ‘30 for 30’ Is a YouTube Series by a “Cranky, Middle-Aged Sportswriter”

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.

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:

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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.

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 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 they’re like, “No, I’m telling you. I’m telling you.” And I was like, “I mean, it sounds kind of fun, so I’ll 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 don’t know why. I can’t even understand why that one blew up, but it’s been, like, this kind of steady growth since. Every now and then some of them do particularly well; there’s 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. It’s kind of funny. They want to do shows where I travel around, like, do shows in different locations. And I’m like, “Nobody’s gonna want to come and see me.” I swear I’ve said that 17 times, “Nobody’s gonna want to come and see me.” Like, why would you? And they’re like, “No, you’re wrong. I’m telling you you’re wrong.” I’m not as reluctant as I used to be because I was wrong about the show as a whole, maybe I’m wrong about this too. I don’t know. But, I mean, look, if they want me to go to whatever, Tampa, Fla., or Toledo, Ohio, and talk sports, and I don’t know — sure, I mean, I would do it.

What about sponsors?

Oh, we recently have gained sponsors. It’s interesting because I think would have had sponsors quicker, but I told [producers] very early on that I won’t do anything with gambling. It’s easier in the sports space right now to get gambling, [but] I’m 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, “Don’t worry.” I’m sure it wasn’t their first choice, not booking gambling ads. So we’re sponsored by a card-collection company and a protein powder.

When you say you’re “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 don’t give a shit about it. They don’t care — they’re happy about it. Just like when cigarette companies would say, “We don’t want kids smoking,” but wink, wink — we’re 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? I’m not nearly, nearly, nearly nearly— I don’t have one/one-millionth the wealth of LeBron James, right? I just don’t need the money that badly that I’m 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, it’s … not even close. Not even in the same ballpark.

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

I gotta get on TikTok.

TikTok is the best. It’s been a career revival. I only got on because— so, in February 2024, a bunch of layoffs happened in journalism. I went on Twitter — I’m 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 there’s a website called The Defector — it used to be Deadspin, basically it’s 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.

I’m 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 don’t know. You know, like, I’ve had titles for my books that I thought were perfect, and the publisher’s like, “We’re not going with that.” I’d 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 there’s a network called Showtime, so they didn’t want to have a Showtime TV show. I wasn’t thrilled, but I didn’t ruin my day or anything.