Why Are All Your Cool Friends Listening to How Long Gone?

Chris Black and Jason Stewart on their bro-y culture podcast’s unexpected appeal.

Jason Stewart and Chris Black. Photo: Cobey Arner
Jason Stewart and Chris Black. Photo: Cobey Arner

On a crisp October evening, the line to get into the Bowery Ballroom was long enough to wrap around the block. It was filled with lower-Manhattan and Brooklyn types: hoodies, denim, good jackets. Demographic: lots of men, mostly white, mostly working in media or advertising or fashion or something adjacent (probably). A few spots down from me, two guys were talking podcast networks and Spotify deals between pulls from a vape pen.

Playing the Ballroom that night, a storied venue usually reserved for indie bands and the likes of Patti Smith, was How Long Gone, the so-called “bicoastal-elite podcast” hosted by Chris Black and Jason Stewart, as part of its live tour spanning ten cities. The tour would have included 11 cities, but the Nashville show a few nights before was scrapped owing to low ticket sales. Tonight’s gig, however, was sold out. By the time curtains lifted, the room was packed so tightly you could barely wiggle through the crowd to the bar.

The show was a bit of a mess, however. Against a background sporting a sponsorship credit for Anchor, the Spotify division that frequently advertises on the show, Black and Stewart kicked off the night’s festivities with what amounted to a short, somewhat obvious set ragging on the cities they had just played. Stewart went for an Alec Baldwin joke just a few days after the Rust shooting accident; it landed with a thud. The interview segments were all over the place, stilted and awkward in equal measure, even if the night’s guests were intriguing: Interview magazine editor-in-chief Mel Ottenberg, comedian Lauren Servideo, and anonymous downtown personalities and podcasters the Ion Pack. (Alison Roman, an early guest on the podcast, was supposed to appear that night but ultimately wasn’t able to make it. “Roman decided she had to go upstate or something,” Black said onstage. “I’m assuming she’s making kimchee out of ramps, some important business thing,” added Stewart.)

For the most part, the crowd that night seemed to enjoy just being there, though it did occur to me that, given the podcast’s cliquey appeal, many of the 500 or so people in the room were probably connected to the hosts at least to some degree. It was a tricky scene to parse.

How Long Gone in general can be a tricky phenomenon to wrap your head around. Over the past year, the show is said to have quietly but clearly become a favored podcast among what normies like myself might call “cultural insiders,” “those in the know,” or, more simply, “cool people.” Fans include the playwright Jeremy O. Harris, the New York Times pop-music critic Jon Caramanica, and Call Your Girlfriend co-host Aminatou Sow, though it should be noted that two of these individuals have been guests on the show before. The podcast has broken into my regular listening rotation as well, though I’m still trying to figure out why.

“To me, it’s an extremely inside-baseball micro-scene report,” Caramanica, an early guest on the show, said when I asked him about its apparent resonance with the culturally hip. “A lot of what Chris and Jason are doing is skipping the text for the meta-text — there’s a lot of unspoken foundational knowledge.”

Since its launch as a pandemic project in March 2020, How Long Gone has endured several rounds of buzz. This included a glowing profile in Vogue last November and another in the New York Times shortly before the start of the tour. The announcement for the tour, made via Rolling Stone, came packaged with another marker of prestige: In what appears to be a first, the podcast has signed a deal with Jagjaguwar, a vaunted indie-rock label that reps acts like Bon Iver and Angel Olsen. That deal involves the production of a peculiar artifact: How Long Gone Adds Color, a double-CD set containing a curated list of 11 songs from across the Jagjaguwar universe with interstitial commentary provided by Black and Stewart. (Sample color: “I didn’t realize Sharon Van Etten was in the Twin Peaks reboot. Did you catch that?” “I barely caught the first Twin Peaks. Tough to follow, even with drugs.”) The set comes out this week.

For the uninitiated, How Long Gone can be a hard sell. This is partly due to its substance being hard to pin down but mostly has to do with its hosts being exasperating to observers (including many of my colleagues, for example). These reactions are reasonable; I won’t deny it. To begin with, any description of How Long Gone probably has to lead with how it’s a podcast hosted by two straight white dudes who use the platform to deem whether things in the culture — a culture that is rapidly shifting away from and/or actively negotiating its relationship with straight white dudes — meet their standard of cool or uncool.

You can already see the problem here. Actually listening to an episode can be a gamble too: The two men are prone to discuss music, fashion, parties, brands, expensive restaurants, and luxury goods in no particular order but with a very particular kind of confidence. Whether expressing disdain for the fandom around Succession or extolling the virtues of flying Delta One, they seem motivated by a strong belief that “coolness” remains a thing that tangibly exists, can be attained, and is desirable. All this results in a specific, aggressively tribal vibe, describable as shock-jock-lite or “generally in the direction of being an asshole,” depending on your tastes.

The whole thing sounds like a stereotype, yet something about the show has an unexpected pull in this particular cultural moment. There’s an implicit connection to the aesthetic of the Dimes Square scene, which manifested as a kind of response to a public culture that’s obsessed with saying all the right things at all times. (“Are we meant to keep retweeting, liking, reposting, and sharing echo-chamber content that honestly becomes boring and dangerous after a certain point?” reads the manifesto of The Drunken Canal, the unofficial rag of the scene.) Of course, Black and Stewart, who are 39 and 41, respectively, are much older than the usual faces of that subculture, but they do nevertheless retain its appealing sense of freedom.

“They remind me of engaging with culture in the pre-2008 era,” one avid listener, an educator in her 30s named Jenny who didn’t want her last name used, told me. “Your algorithm used to be you and the places you used to go, where you found out what was cool by hanging out with people.”

“My coolest friend listens to this show,” said another fan, a podcast executive. “She’s someone who is legitimately Dimes Square cool.” She added, unprompted, “She is also potentially the wokest person I know.”

Frankly, I can’t tell which parts of this very niche cultural spectrum are supposed to be the cool ones anymore. In many ways, the counterintuitive nature of How Long Gone is what makes it so alluring, but it raises a lot of questions. What, exactly, makes this rambling podcast by two straight white men so cool? Is this cool? Is it even allowed to be?

“Bro, do you think I can explain this shit?” said Black, when I visited the pair back in October.

We were in the greenroom a few hours before the Bowery Ballroom show. Rebounder, the indie band that served as the musical accompaniment in the tour’s first few cities, was doing sound check downstairs. Stewart was already a beer in. Black, who is sober, was pressed into the couch, feet on the table in front of us where our Liquid Deaths sat.

“Look, hopefully that’s just the je ne sais quoi we have,” he said. “But as we’ve tried to distill this down for other people over the past year, what we’ve been able to say is just, like, we’re two friends talking, and it doesn’t matter what the subject is. You feel like you’re part of a conversation that’s easy to jump in and out of. I mean, a lot of podcasts, you have to pay attention, know what I mean?”

Black is the hustler, the energy man. He speaks quickly, thinks out loud, and works his interlocutors like a featherweight boxer. In another life, he managed the pop-punk band Cartel, which was featured in an MTV program in the late aughts in which they were made to write and produce an album in 20 days while living inside a broadcast “bubble.” Today, Black works as a creative consultant, having worked in the past with brands like Stüssy and Thom Browne. (Black, I should note, occasionally contributes to New York’s the Strategist.)

In contrast, Stewart is quieter in person, content to slink in the background during our chat. A former EDM DJ who, among other achievements, was once recruited to teach Zac Efron how to spin for the 2015 film We Are Your Friends, Stewart is nowadays what one might call a “creative entrepreneur.” He made two other podcasts before How Long Gone, a food show called The Stew and an interview show called Tall Tales (Stewart is six-foot-nine), both of which he co-hosted with other collaborators. The roles feel contiguous: Here’s someone who’s good at teeing other people up to do their thing.

Earlier this year, Stewart committed to really sitting down to produce the show. “I made a resolution that I would edit every single episode to a T, not just hit ‘record’ and publish Red Scare–style,” he said. “It’s more hours spent, but I enjoy it.” He listens through every recording like game tape, occasionally giving notes to Black for future conversations. Given how loose the show feels and how unflattering the pair can come off, this is a curious factoid. Then again, the logic behind spraying and praying is that it’s all content. “Of course, we have bad interviews, but it’s still important to upload that,” said Stewart. “You heard Marc Maron talk to Jerry Seinfeld. That shit was disastrous,” said Black.

“I love when a podcast is going downhill,” Stewart added. “Let’s make it fun. If the house is on fire, let’s throw gas on it and turn it into a spectacle. Japanese Breakfast wasn’t really onboard with our whole vibe, but if you stick around to the very end and you’re a little bit of a nihilistic person, maybe you could be like, That’s the best episode I’ve ever heard.”

Black mostly handles guest outreach, a role that plays into his natural talents and agency-world network. “I’m very willing and able to email people all the fucking time and get them to come on,” he said. “It’s not that hard when you like doing it.”

The show’s bread-and-butter guests are media, creative, advertising, and fashion types of a certain age who you imagine dining at the same restaurants as Black and Stewart.

“There’s something overly knowing and occasionally indifferent about how Chris and Jason approach interviews,” Caramanica noted. “It’s almost anti-interviewing, and that can lead into more natural conversation. Sometimes, when you know a tremendous amount about a topic, it’s nice to have a conversation with someone you don’t have to do the explanatory work with.”

The original cover art, a play on the New York Times’s The Daily.

The guys also have an obvious talent for attention. Among the more amusing examples: the show’s original podcast art, an unmistakable rip-off of The Daily’s. The duo was compelled to change the art after the Times sent a complaint. “Although it was still similar, it was no longer identical, so our concerns were amicably resolved,” a Times spokesperson told me. Black and Stewart later sold T-shirts about the whole thing.

Black tells me they don’t mull over things too much. “If we do, it becomes work, you know?” he said. This is perhaps the core of their creative practice. They make episodes at a high enough pace and volume at which they don’t have to think and possibly question themselves. “We set things up in a way, probably subconsciously, that we couldn’t wiggle our way out of it,” said Stewart.

The actual, measurable size of How Long Gone’s audience remains unclear. Both the New York Times and Vogue profiles cite the show as reaching “monthly listeners” in the six figures within the first few months of its launch. The meaning of that metric isn’t the cleanest, even in the notoriously hard-to-measure podcast business. When asked about average downloads per episode, which tends to be a more accepted metric, the guys replied with a number smaller than expected, about 30,000, though they said they haven’t checked recently. In any case, Black and Stewart claim they don’t pay close attention to the figures. “Being relevant culturally and people caring about it is more important to me than the numbers,” said Black. “I don’t even look at them.” (Earlier this month, during Spotify’s Wrapped season, Stewart tweeted a screenshot indicating the show’s streams had grown by 222 percent over the past year.)

“That’s the thing — it’s all about the optics,” said Stewart.

And from an optics standpoint, the show gives off the feeling of an upswing. There are the glossy profiles, the growing prestige of the guests (Charli XCX, Mike Mills, Jake Lacy), the move to produce a double-CD set (“We grew up listening to this format,” replied Black, when asked about the decision), the intermittent merch drops that sell out quickly, which have included hats, tote bags, canned coffee, and a limited-run vegan breakfast sandwich. The tour, similarly, was designed with an eye for flair. “I wanted to be the first podcast of this kind to do venues like this,” said Black, regarding the Bowery Ballroom. “We didn’t want to play corny theaters.”

If the How Long Gone guys have a specific gift, it’s that of making something out of nothing. One gets a sense of them as men willing themselves into notoriety. In addition to everything else that it is, How Long Gone is a case study in marketing, an example of the kind of amorphous influence “coolness” can still have in a world obsessed with data. What’s more important, anyway? Ambiguous download counts or a growing mythology that includes your own line of coffee?

Of course, Black and Stewart’s brash style has its detractors. Even the show’s fans admit having qualms. For those bothered by fat-shaming jokes and hotness evaluations (judging people as “fives” and “sixes”), it can be a lot. These are guys who were already making jokes about COVID on a public forum as far back as April 2020, instead of reserving that sort of gallows humor for private conversation like the rest of the cultural elite.

But How Long Gone’s followers find a way of squaring these antics. “I think of it more as a comedy podcast than a lifestyle one,” said Kevin Lozano, a magazine editor, when asked about the show’s appeal. “The way the two see the world is absolutely not the way I do, but the way they navigate it, sometimes clumsily, sometimes elegantly, is funny to me. Even if I don’t like what they’re saying, I find myself chuckling.”

“I think it’s hard for them to get canceled; everything is said with such a loud wink,” said the podcast executive who told me her coolest friend likes the show. “They don’t edit themselves into being better people than they actually are. Say what you want about them, they’re definitely committed to being interesting.”

Chris Kelly, who runs a podcast studio in Vancouver, felt similarly: “It’s not Joe Rogan or Barstool Sports, but if they amped it up a little bit more, we’d be in uneasy territory. That said, they seem to be smart enough to know where the line is and when to call themselves out.”

When asked if they ever worry about coming across as insensitive, Black and Stewart waved the question away. “Oh, I don’t give a fuck about that,” said Black. “If you get offended by me saying something you like is whack, this ain’t for you, chief. That’s the world we live in.”

“If we’re not turning enough people off with our opinion, then we’re not doing anything anyway, you know?” said Stewart. He also shrugged off the less flattering perceptions of their show. “If people categorize us as a bro podcast, then maybe we get some portion of a bro-podcast audience and then we can expose them to Hari Nef, a trans person, and that might not be something they’re used to hearing, or a gay black playwright that’s so far out of a bro’s world. And they get to hear a conversation, and hopefully they get to learn some things. And then other parts of the community, maybe they get to hear Charli XCX talk to a bunch of bros about swimming pools or something.”

“Jason and I are just sweet, normal guys deep down inside,” Black added. “We’re easy to talk to. We’re not confrontational people. That’s not what our approach is. Being opinionated or being confrontational are two different things.”

Despite what seemed like a spotty night in New York, Black and Stewart were happy with their live experiences. “On the whole, the tour was incredible,” Black told me. “To have a majority of the shows sell out and to see that these people are real … it’s an incredible feeling. We’re too old for this shit, so it was also exhausting, but overall it was probably the best thing we could’ve done at the time we did it.”

I asked how far they were hoping to take this. “TV, for sure,” Black replied without missing a beat. Stewart was less laser-focused. “I would be a hundred percent happy to just stick with podcasting and get a Joe Rogan deal and be rich as hell and do whatever I want,” he said. “But it would be cool to do a TV show where you can have a band play, where you can do a cooking segment and bring in our chef friends, that kind of thing. Like HBO.”

They describe their proposed TV series in the vein of another podcast-to-television jumper. “Desus & Mero do a great job, but I think there’s more room for that kind of thing,” said Black. “I believe we can service a market that’s relatively underserviced.”

Two white men evoking Desus & Mero as a point of comparison and claiming to represent an underserved market — in this climate? It’s all too easy to roll your eyes. But these guys think they can pull it off. And what is the straight white culture bro if not persistent?

Why Are All Your Cool Friends Listening to How Long Gone?