“Does the world need another podcast with two straight, white guys?” Stewart asks rhetorically in the first episode. “No,” he answers. “But we’re tatted up, we aren’t giving much to the economy, and we’re ready to give you our medium takes.”

Despite this, HLG has racked up 150,000 monthly listeners since its debut in March, and has hosted a lengthy list of guests. Undeniably, a certain degree of navel-gazing has fueled the show’s success. Simply put, says Black, “media people love hearing other media people talk.” Recent guests have included author David Coggins, New York magazine’s Matthew Schneier, writer Evan Ross Katz, Vogue’s Liana Satenstein, and the New Yorker’s Hannah Goldfield. Earlier in October, it was announced via Twitter that New Yorker writer Naomi Fry was flown out on Diplo’s jet just to make an appearance on the show. “We like to joke,” Black says when asked about it.

HLG’s guests have gone beyond media circles to include Saturday Night Live’s Bowen Yang, playwright Jeremy O. Harris, and Tavi Gevinson. There is one criterion the pair use to winnow down guests: “They have to be down to clown,” Stewart says. “Meaning, is this person going to be down to make fun of themselves, and will I actually enjoy talking to them for an hour? Will they let their guard down? You kind of get the vibe.”

The duo has an effortless ability to make their guests feel comfortable enough to drop perceived personas. A former editor in chief of a major culture magazine reveals his relationship with body dysmorphia. A world-renowned fashion blogger discloses the uncertainty of their next step in their career. Recently, The Hills alumna Whitney Port made her debut on How Long Gone and touched on how her TV persona continues to follow her. “People have that preconceived notion about me, being a straight-edge bae from Brentwood! But I have a knuckle tattoo, man!” Port and the hosts went on to joke about men’s “pancake-y asses” and how she’s no stranger to indica and sativa.

Another reason the show continues to grow is that the pair do not shy away from difficult subjects. “They’re just very real and they don’t really care about what people think of them,” says Chrissy Rutherford, a brand consultant and contributor to Harper’s Bazaar, who joined the two to talk about Barry’s Bootcamp, screen times, birth charts, and race. “They aren’t afraid of having those difficult conversations,” says Rutherford. “They used their platform and invited various Black guests and gave us the space to say what we needed to say. They just listened. Yeah, they don’t really talk politics. But I think it’s worth noting that they recognized the importance of conversation at that time.”

HLG has recently passed the 100th-episode mark, and the hosts tell Vogue that they hope to interview people such as Phoebe Bridgers, Nancy Jo Sales, and PJ Vogt from Reply All in the future. Recently, the two have expanded into livestreaming. In a sort of low-budget, late-night format, the two sit on a couch and invite guests for in-person interviews, comedic banter, or musical performances. “Obviously, the visual element lets us meet our viewers in another way,” Stewart says. “We can dissect someone’s social media account together, or even bring up a photoshopped picture of Chris as Tekashi 6ix9ine.”

Comedic relief aside, Black and Stewart believe that the podcast is truly reflective of desire for a more personal, unscripted conversation. The greatest reward is “creating a universe of interesting and engaging people who just want to come together to have a good time,” says Black. “Everything else out there seems dark and scripted,” says Stewart. The aim will always be to bring people from all sorts of backgrounds to “laugh as a family,” says Stewart. There is pride in being able to prove that “straight guys can kiki too.”