A Night At The Carlyle With 'How Long Gone'

It’s Tuesday night on the Upper East Side and Cafe Carlyle — the small, legendary Jazz restaurant inside of The Carlyle, a Rosewood Hotel — is quickly filling with familiar faces and names. A mix of designer bags and worn-in canvas totes hang from the backs of the gold chairs, servers in white coats move through the room, dropping off drinks, as friends excitedly catch up. At 8 p.m. the lights dim, a familiar tune begins to quietly play, and Chris Black and Jason Stewart, old friends and podcast co-hosts, take the stage many legendary performers—but never before two podcast hosts—have stood on before them. For one night only, How Long Gone is live at Cafe Carlyle.

“I don’t know how some of y’all got in here, it was supposed to be a tight list,” Chris jokes within seconds of holding the mic, Jason sitting in the chair next to him, microphone and martini (Titos, with a twist) in hand.

For anyone who isn’t a regular listener, HLG is a “bicoastal-elite” culture podcast where the pair talks about fashion, pop culture, music, and more. If you had to assign it a category, it’d be fair to say the podcast toes the line between bro-talk and comedy. “We want our show to be entertaining, at the very least, and comedy is how we entertain,” Jason says. “Comedy is a spectrum and we’re just one small petal on that flower.” He goes on to compare HLG to other similar, bigger podcasts, like SmartLess. “Even though we’re a bros-talking-podcast, I think we’re doing the same thing as a lot of other bigger podcasts, just on a smaller scale and more edited,” he explains. “It’s just privileged people being interviewed about funny stuff but it’s in a way that nothing happens. If there’s a bad joke, we edit it out. If there’s a bad tangent that goes nowhere, you’ll never hear it.”

With over 500 episodes, and roughly half a million monthly listeners, episodes have featured musicians like Caroline Polacheck, The 1975, and Phoenix, writers and editors such as New Yorker’s Naomi Fry and Highsnobiety’s Willa Bennett, comedians like Mary Beth Barone, and recently — right in time for the 500th episode — Andy Cohen. While thinking of future dream guests, Chris and Jason throw around names like Liam Gallagher, Martha Stewart, Katt Williams, and Ina Garten. “The throughline is legacy people who know what they’re doing and maybe don’t always get the platform to talk how they want to talk,” says Jason.

Chris, Jason, and Naomi Fry last night at The Carlyle.

Unlike their other live shows, this night is quasi-off-the-record. The room isn’t filled with fans who paid for tickets and waited in line to hear the voices they listen to while doing laundry or running errands come to life in front of them. Instead, the intimate space is filled with nearly 100 of the duo’s closest friends, family, and colleagues (plus a couple of on-duty reporters to catch it all). Take a good look around the room and you’ll notice it’s filled with the people who write the articles you often share, or the books you love, or who designed the bag you always get compliments on.

It shouldn’t shock anyone to learn that the pair’s small, private event has a guest list of some of the biggest names in the fashion and media world, either. Given Chris and Jason’s years in the music, media, and fashion industries, their personal and professional circle is understandably expansive. Vogue columnist Raven Smith, J.Crew Art Director Bex Farleigh, GQ Global Editorial Director Will Welch, and designer Susan Korn are only a few of the faces filling the space, excited to watch (and heckle, when needed) their friends.

As their hour kicks off, the guys quickly settle into their rhythm. Chris tells us Jason often feels out of place in high-end situations, suggesting he struggles with imposter syndrome. ”Imposter syndrome is when you think you don’t belong in the place you do belong. What is it called when you know you don’t belong? When it’s confirmed? I’m just an imposter,” Jason replies. Chris reads a handful of Drake’s poetry from Titles Ruin Everything: A Stream of Consciousness and Jason describes his self-served breakfast in bed from that morning: a “handcrafted Nespresso and a dry-aged Levain cookie from the night before.”

Chris admits he paid a not-so-small fee (“about $7,000”) for an “anti-aging doctor” who’s responsible for the peptide shots he now gives himself, right in the ass cheek, each night before bed and the room lets out an audible groan. “Don’t do this. You wear Dior slides, don’t do this to me!” Chris shouts towards a friend in the back who’s booing him. Despite the cost, Chris stands by the peptides—his energy levels and joints have apparently never felt better.

“Every person you’d want to be here tonight is on vacation,” Chris jokes, explaining why there’s no special guest officially on the bill. “Because that’s what rich people do in the summer in New York, and that’s why I’m feeling really poor right now and I hope you guys are as well.” Soon, they look to the crowd to fill the empty seat between them.

Whether the guests happily slide onto the empty chair or reluctantly approach the stage — “Come on guys, what am I doing up here?” Welch asks more than once—they do what HLG does best: They give listeners an honest glimpse into the conversations they’d probably be having with these same friends if they were sitting at a table at Corner Bar or on their couch at home. Each time someone new is plucked from the audience, the conversation continues seamlessly.

Jason and Chris discuss The Real Housewives of New York with Fry and Dead & Company’s final tour with Welch, designer watches and eating on airplanes with Creative Consultant (and the brain behind @dimepiece.co) Brynn Wallner, and they share their stance in the great no-show-sock debate (they’re anti-no-show, of course). “I'm dazzled by anyone who has the gift of gab and both of the boys are blessed,” Korn says.

Like many podcasts that began mid-pandemic, How Long Gone started as a joke. Unlike many of those same podcasts, Chris and Jason haven’t lost steam nor struggle to maintain success. “We take it seriously,” Chris says. “There’s a level of respect we have for the medium and the listener that they respond to. It doesn’t feel like they’re being talked down to or made fun of, it feels like they’re part of it.”

After the show ends, David Cho, Creative Director, long-time friend, and former HLG guest, attributes the duo’s success to their self-awareness, nuance, and humor. “This show is genuinely representative of what they do: extremely nuanced and interesting conversations for people who believe that the binary of the current media landscape requires actual self-awareness,” Cho says. “I mean, you see that in Chris talking about taking the peptides! You need to be honest with yourself to actually have any intimacy with others. That’s what’s fun about this. It’s the same reason why like twelve people asked me if I could get them in tonight.”

Soon, their time under the bright spotlight wraps and they thank everyone for coming uptown for the evening to participate in the slightly chaotic, wildly entertaining, winding conversation. “We really appreciate you guys, this is fun for us,” Chris says affectionately. “I can’t wait to wake up and go back to my shitty life downtown tomorrow.” People hang around the room for the next hour or so, finishing drinks and mingling.

As the night comes to its end, everyone begins breaking off. Some walk across the floor to Bemelmans Bar or head towards the elevator, others straight to the Uber, or train car, that’s waiting for them, and many to the front of the hotel, moving through the revolving doors with unlit cigarettes in hand, eager to taste the smoke that’s always best a couple of drinks in. Desperate for a belated dinner—a few martini olives can only sustain you for so long, after all—I say my goodbyes and start my journey home.