Chris Black & Jason Stewart of “How Long Gone” Talk Live Performance and Podcast Culture

When Chris Black and Jason Stewart started their podcast, How Long Gone, in the early days of the COVID-19 pandemic, they had no idea it was going to be a massive success. Each episode, the two “bicoastal elite” friends — Black is a New York–based brand consultant who has worked with brands like J.Crew and Thom Browne, while Stewart has DJ’d under the moniker Them Jeans and calls Glendale, California home — discuss pop culture, fashion, music, and more with their (sometimes famous) friends and other guests. More than four years and 700 episodes later, they’ve interviewed everybody from actors (Lee Pace, Rachel Sennott), to chefs (Alison Roman, Jamie Oliver), to musicians (Charli XCX, Moby), and done live shows around the world. With three shows a week, it’s a non-stop pace — but to hear the duo tell it, they wouldn’t have it any other way.

“It’s like going to the gym. Once you realize how much you like it, and how much it benefits you, you’re not going to stop doing it,” says Black over a video call. “I think that’s kind of true about this in a lot of ways. What am I going to do during Christmas, sit around and eat cookies? That doesn’t appeal to me.”

“What we’re looking for is that moment on the Zoom call when you see their face or their eyes change, when they’re like, ‘Oh, this is not another one of those things where I have to do my canned, media-trained responses.'”

Jason Stewart on How Long Gone’s candid interviews

Adds Stewart, “We recorded an episode of the podcast the morning of my wedding day because my wife said, ‘I don’t want y’all podcasting during the honeymoon so get this shit out of your system.’”

This consistency, coupled with the duo’s ability to effortlessly switch between lighthearted anecdotes (like comparing their Delta club statuses) and more serious topics (like Black’s sobriety after battling an addiction to OxyContin in his 30s), and a knack for getting guests to do the same, have earned them a loyal following of fans (or “Goners,” as they’re known). Whether it’s a Grammy-winning singer or a menswear magazine editor, they approach everybody with the same amount of research, and both say one of the biggest markers of a successful interview is when they can get their interviewee to forget about what they’re promoting.

“What we’re looking for is that moment on the Zoom call when you see their face or their eyes change, when they’re like, ‘Oh, this is not another one of those things where I have to do my canned, media-trained responses,’” says Stewart. Despite many of their peers making the jump to video, the co-hosts cite the logistical headaches, and are adamant they’d prefer to concentrate on compelling storytelling. “I know 100 podcasters and the ones who do video all hate doing it,” says Stewart. While they have more people involved now, with ad sales, distribution, and marketing, Black and Stewart still handle all day-to-day operations, with the former booking the guests and the latter editing.

In recent years, they’ve brought the show on the road, performing to audiences in cities including Toronto, New York, Melbourne, and Stockholm. The format typically sees the duo riffing on a number of pre-planned topics and occasionally interviewing guests. “I think I was particularly concerned, like ‘Who are these people going to be?’ ” admits Black. “And I’ve been pleasantly surprised since day one. Even people that stop us in the street or in the airport or whatever, everybody’s cool, everybody keeps it moving, everybody’s respectful.”

For the duo, who grew up going to punk concerts and later got involved in DJing, these shows (and after-parties) have been an opportunity to play hallowed music venues while fostering community offline. “It’s like The Grateful Dead,” jokes Stewart. “The live show’s fine, but it’s more about the parking lot vibes.” “See How Long Gone at Webster Hall and you can definitely get a grilled cheese with acid in it right outside,” adds Black.

Although they aren’t planning on pivoting to video any time soon, don’t be surprised if you see Black and Stewart on your screens in the not-so-distant future. They’re signed to talent agency CAA, and have hosted red carpet interviews for GQ (where Black has a column) and FX series The Bear (actors Ebon Moss-Bachrach and Matty Matheson have appeared on the show).

“When you get a New York Times profile, it makes you feel legitimate, no matter how much money you’re making or how many downloads you’re getting. But you also realize that none of that stuff matters. The consistency is the most important thing.”

Chris Black

“When we started four years ago, everyone was like, ‘Man, Hollywood is in a really bad place, there’s writers’ strikes and actors’ strikes,’ and it has only gotten worse,” notes Stewart. “Until we figure out a way to make something visual work for us, I think there’s no rush,” says Black.

In the meantime, the duo isn’t resting on their laurels, and fans can continue to expect the usual pace of episodes.

“We don’t really look inward as far as How Long Gone goes,” says Black. “There’s episodes that feel good and moments that feel good of course. When you get a New York Times profile, it makes you feel legitimate, no matter how much money you’re making or how many downloads you’re getting. But you also realize that none of that stuff matters. The consistency is the most important thing and that’s what makes it feel the most successful. We don’t miss one, we just keep doing it. And the conversations hopefully get better and better.”

Feature photo by Karolyn Pho.

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