Ryen Russillo says screenwriting ambitions drove his free agency decision

Ryen Russillo has been one of the more recognizable voices in sports media for the better part of 20 years. He’s also been trying to break into Hollywood the whole time, and last fall, that pursuit had a direct say in where he ended up.

On The Colin Cowherd Podcast this week, Russillo said that by the time he was weighing his options after leaving The Ringer last fall, he had already sold a pilot to a major network and was deep in development with a prominent producer, and that shaped which offers he was even willing to consider.

On a recent appearance on The Colin Cowherd Podcast, Russillo revealed that by the time he was weighing his options after leaving The Ringer at the end of his contract last fall, he had already sold a pilot to a major network and was deep in development with a prominent producer, and that shaped which offers he was even willing to consider.

“When it came time for the decision of what I wanted to do, I had sold a pilot to a network, hooked up with a big-time producer, sold it to a major network, and was developing that,” Russillo told Cowherd. “Some of the opportunities that were coming along, I was like, well, if I say yes to this, then this whole script thing — this dream that I can never imagine a scenario where it doesn’t work out for me — I wish I’d just shut the f*ck up about it and never talk about it. But it was a key part of whatever the next place is. They have to understand that this is something that I’m still trying to do. Because, look, you learn pretty quickly that the writing’s the easiest part, and then selling it is really hard. And then getting it made after you sell it is like 10 times harder than all that other stuff.”

Ryen Russillo says his screenwriting dream drove his free agency decision:

“I sold a pilot to a network…this script thing, this dream – I wish I’d shut the fuck up about it, never talked about it – the new place needed to understand this is still something I’m trying to do” pic.twitter.com/3R5Rxgc5jp

— The r/BillSimmons Podcast (@rBillSimmonsPod) May 22, 2026

Russillo started writing in 2002, before he ever got his first job in radio, before ESPN, before any of it. He put it aside when he landed a gig in Boston and spent the next several years too broke and too busy to give it serious attention. It wasn’t until he was wrapping up his run at ESPN — before leaving for The Ringer full-time in 20219 — that he finally committed to finding out whether he could actually do it.

“The feedback on some of the more recent scripts has been terrific,” he told Adnan Virk on the Cinephile podcast in 2021. “I even had a couple people write back to me, ‘Hey, this movie would’ve sold in two seconds in 2005,’ but that’s not where we’re at right now. I don’t want to make excuses for it. It will happen. Not everything happens on your schedule. I was able to sell one thing, which felt kind of cool, but it’s a really hard thing to get into. And even with the success I’ve had, it doesn’t guarantee you anything.”

In that same conversation with Virk, Rusillo noted he had partnered with some prominent names on various projects and had managed to sell one thing. Deadline reported in 2022 that Russillo had signed with UTA for scripted television representation and was developing a project at the time, and by last fall’s free agency, he had a pilot sold and in active development with a major producer at a major network, though it’s unclear whether the two are related.

Russillo landed at Barstool, launching his own production company with Dave Portnoy’s investment and bringing Steve Ceruti and Kyle Crichton with him over from The Ringer. Barstool officially announced the hire in September, with Russillo set to continue his podcast while developing new content under his own banner. The video version of his show began airing exclusively on Netflix in January as part of Barstool’s broader streaming partnership with the platform, which also includes Spittin’ Chiclets and Pardon My Take.

By his own account, the Barstool move has been “even better than I could have hoped for.”