Hanging Out With ‘How Long Gone’ at The Carlyle

For one night only, the “How Long Gone” crowd took over Café Carlyle at the legendary Carlyle hotel on New York’s Upper East Side, bringing with them a healthy dose of downtown style not typically seen north of 14th Street.

Hosted by Chris Black and Jason Stewart, “How Long Gone” has emerged as a must-listen podcast since its conception in 2020. Guests often include media fixtures and fashion personalities, who fittingly made up lots of the family and friends crowd: Raven Smith, Emily Oberg, Beverly Nguyen, Susan Alexander, David Coggins and Alex Tieghi-Walker were some of the faces in the room, spaced around the Café Carlyle at tables dotted with martinis, Champagne and dishes of the signature bar snacks.

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Rather than their typical one guest per show, the Carlyle “HLG” show featured a rotating cast of “friends of the pod,” past guests including The New Yorker’s Naomi Fry, GQ’s Will Welch, The Wall Street Journal’s Jacob Gallagher and creative consultant Brynn Wallner. Fry was tapped for her expertise on the new cast of “The Real Housewives of New York;” Welch shared insight from the Grateful Dead’s San Francisco show; Gallagher debated the validity of no-show socks, and Wallner defended Cartier watches.

Chris Black and Jason Stewart
Chris Black and Jason Stewart

Stewart and Black have taken their show on the road before with success, doing shows at concert venues all over the country, as well as the U.K. and Canada (later this summer they head to Copenhagen Fashion Week and this fall, Australia). The opportunity to do a live show at The Carlyle was a no-brainer for them, once it was presented.

“Our dear friends at Purple PR were like, ‘would you guys be interested in doing the show at The Carlyle? And I was like, ‘yeah, bro. Tell me when,’” Black said before heading onstage, from up in his hotel room.

“Dream come true,” Stewart added.

The concept of a friends and family show — invite only, free admission — rather than their usual ticketed events was fitting for the venue.

“This is more of a loose vibe since no one is paying to be here,” Black said. “We feel less responsible for the time they have.”

“The way that this show is an unpaid opportunity, it’s also an opportunity to give them a show that is unpaid for,” Stewart said. “I’m normally really nervous because I have guilt and imposter syndrome when we have 500 people who bought tickets with the Ticketmaster fees and everything — you feel the pressure to do well. And all of that has been removed.”

Black, meanwhile, was feeling the need to deliver.

“I only care for VIPs,” he said.

Guests Brynn Wallner and Will Welch.
Guests Brynn Wallner and Will Welch.

While the original concept came as a pivot post SAG strike-induced cancellations, the idea worked the more they played with it.

“There’s a lot of people in the room that have either been guests or that we’re real friends [with]. And we know they can handle it,” Black said. “So we’re going to bring people up, and have them defend themselves. It’s a different crowd. It’s a different room. And I think approaching it differently works.”

“Have you been to Benihana before?” Stewart quipped. “Have a seat.”

In the last year, Black and Stewart revealed they signed with CAA; the future plan is a move further into the Hollywood space.

“Television is what we are working on. We were working on it quite diligently. And now I think we’re going to have to wait a little while for things to level out,” Black said, referring to the ongoing WGA and SAG strikes. “But that’s the plan. Our timing wasn’t super great. But our partners and the pitch is dialed and we feel pretty great about it and I think it’ll find a home. But in the meantime, we’re very grateful to have a podcast where we produce hours of content per week for free. And, you know, it’s only getting better.”

“We have some guests [coming up] that I used to idolize until I found out that my wife has a crush on them,” Stewart said. “So now I feel the need to have them canceled. Take them down.”

In the meantime, the duo’s immediate plans include taking in this weekend’s much-hyped double feature: “Barbie” and “Oppenheimer.”

“I want to say I’m a little Barbie-ed out, but I’m going to go see it — and I haven’t seen a movie in the theater in five years probably,” Black said.

“I’m excited to take a full dose of mushrooms and watch ‘Oppenheimer.’ Alone,” said Stewart.

Jason Stewart and Chris Black of podcast 'How Long Gone' at Cafe Carlyle at The Carlyle Hotel in New York City.
Jason Stewart and Chris Black of “How Long Gone” at The Carlyle.

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