Conan O’Brien on how to embrace an ever-changing media landscape

The 2018 launch of “Conan O’Brien Needs a Friend” found the comedian embracing the new-found freedom of podcasting.

“There are a couple of things about doing podcasts that are superior or more fun than doing a talk show,” a quarantine-haired O’Brien said in an interview at TechCrunch Disrupt this week. “When I’m doing the traditional talk show, I’m limited. For years and years and years, when it was on network television, I had to take six- and seven-minute turns, which mean I’m having a conversation with you or I’m having a conversation with someone I’ve always dreamed of talking to, whether it’s Tom Hanks or Jim Carrey or Robin Williams. Then after six or seven minutes, there has to be a laugh and we’ll take a break and we’ll be right back.

“That’s not a natural conversational flow,” he continues. “What you can do with a podcast is really incredible. I can talk to someone for an hour and 15 minutes. We try and trim them back, but for the most part, people let their guard down. The other thing I prefer: no hair and makeup. It sounds like I’m kidding. But after almost 30 years of people caking my very white face with makeup so that I look like I’m still alive.”

Team Coco has produced 10 shows in all, including shows from longtime sidekick Andy Richter and actor Rob Lowe, writers Mike Sweeney and Jessie Gaskel’s intimately titled Inside Conan and a six-part mini-series interview with SNL alum, Dana Carvey.

“I don’t want to set a number goal,” O’Brien says. “I’m amazed — in two years, we’ve rolled out 10 different podcasts, some of them unscripted, but some scripted ones, as well. I’m not sitting around saying, ‘hey, we’ve got to get to 35 podcasts by this point.’ Because I’d like them to be good.”

The talk show has soldiered on, as well, undergoing its own transformations in the process.

In 2019, the program was retooled for a half-hour format. O’Brien dropped the desk and the suit, adopting a looser format perhaps inspired in part by the new freedoms afforded by his podcasting ventures. When COVID-19 made the in-person show an impossibility, he started working from home like so many others, switching to remote Zoom interviews. Throughout it all, “Conan O’Brien Needs a Friend” continued posting weekly interviews.

Asked whether he planned to continue his late-night show after the contract runs out in a couple of years, O’Brien seemed unsure.

“I think it’s a mistake to think of it as, will you stop doing the show, and only do the podcast? Or will you retire and then quietly work on your letters in a shack? I love to create things. I have a lot of energy. I love to try and make people laugh. And so I see All of this converging, I think the message that I would have for everybody watching TechCrunch Disrupt right now is that people need to open up their minds a little bit. If I’m making podcasts, it doesn’t prohibit me from also maybe do maybe doing something, it doesn’t have to necessarily be for Turner, it could be for anybody.”

Multiple decades of success, it seems, have put O’Brien in the relatively unique position of being able to be somewhat platform-agnostic. Not being tied to a single medium is a strong place to be when it comes to bracing oneself for the unexpected technological changes that will continue to disrupt and upend the entertainment industry.

“Five years from now our entertainment may come in pill form,” he says. “You could binge The Sopranos. You could just take a whole bottle of Sopranos and then just drink a lot of water and then, you know, just don’t need any red meat.

“This is gonna sound far-fetched, but I think this is the most excited I’ve been in my career, because there were so many ways to be creative. There are so many ways to make people laugh, and I enjoy these new opportunities. I think when you’re someone who has been around as long as I have, you have a choice. You can be afraid of change, or you can be delighted by it.”