‘2 Dope Queens’ Roast ‘DILF’ Jon Stewart in HBO Premiere

Jessica Williams and Phoebe Robinson reunite with an old friend on the first episode of their new HBO series.

Mindy Tucker/HBO

The road from podcast to television is littered with disappointment. This American Life tried to make the transition a decade ago and lasted just 12 episodes (compared to 636 for the podcast). Serial announced a TV adaptation deal two and a half years ago that has yet to materialize. Comedy Bang! Bang! aired for five seasons on IFC, but never reached the comic heights of its audio-only version.

This week, 2 Dope Queens, the beloved WNYC podcast hosted by comedians Jessica Williams and Phoebe Robinson, is debuting the first of four hour-long specials on HBO. And judging by the first two installments, it is already the most successful podcast-to-TV transfer yet.

It helps that 2 Dope Queens is at its heart a live show. Taped in front of a live audience in Brooklyn, the podcast, and now the TV show, include improvised chats between the two hosts along with stand-up sets from the hottest up-and-coming comics working today and, typically, a casual sit-down interview with a celebrity guest. For the HBO version, the pair has moved from their previous home at The Bell House bar in Gowanus to the regally restored Kings Theatre in Flatbush.

“We thought, what if we created this podcast where we have different stand-ups and storytellers that we love on the show, and they are all people of color or a woman or a member of the LGBTQ community?” Williams said, with Robinson beside her, on her fellow Daily Show alum Stephen Colbert’s Late Show this week. “Because I think we feel oftentimes, as women of color in the entertainment industry, we are supporting characters in other people’s narratives. So we wanted to give not only ourselves the opportunity to be the stars of our own narratives, but we wanted to give those opportunities to other people who are super-funny as well.”

With that in mind, they booked an impressively diverse lineup of comics for their HBO specials. Michelle Buteau, Mark Normand, and Baron Vaughn perform in the first episode and comedians like Search Party’s John Early and Corporate’s Aparna Nancherla will make appearances down the line.

But the centerpiece of Friday night’s New York-themed premiere just happens to be an older, straight white man: Jon Stewart.

As Williams explains, Stewart gave her her first job in New York City when he hired her to be a correspondent on The Daily Show at just 22 years old. The episode was taped months ago, so that means no timely Trump jokes from Stewart. But there is still plenty of fun to be had watching the middle-age comic try to keep up with the aggressively millennial hosts.

When they begin the interview by trying to explain the “rooftop vibe” of their set to Stewart, he shoots back, “I’m not blind.” Asked if he goes to a lot of rooftop parties at this stage of his life, Stewart replies, “No, I don’t get out at all, and this is exciting.” He is similarly baffled by Robinson’s description of her and Williams as “Cocoa Khaleesis.”

“Here’s the thing you don’t know about Jess,” Stewart tells the crowd. “She enjoyed very much when she was on the show, taunting me.” If he was in The Daily Show fixing a coffee, he said she would sidle up to him and ask, “How’s the coffee, old man?”

“I bullied him,” Williams confirmed. “I bullied my boss.”

There is a bit of HBO synergy at work on 2 Dope Queens, at least in the first couple of episodes. Stewart recently announced that he will headline two stand-up specials for the network after his planned topical animated series with HBO fell through. Next week, on the “Hair” episode, the special guest will be Sex and the City and Divorce star Sarah Jessica Parker, who balks at the idea that she is a “hair icon.”

Asked by Robinson about his highly anticipated return to stand-up, Stewart says he’s “not nervous,” adding, “And I’ll tell you why. I’m at the point in my career where I kind of don’t give a fuck anymore. I’m just going to say how I feel and hopefully people dig it and if not, you know, I’ve sheep and goats and a couple pigs. Life is good, man.”

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Then, when Stewart describes his fashion statement as “homeless old man,” the hosts defend his look. “You look great, you’re like a DILF,” Robinson said.

“That’s what young women say to older men who don’t look that great,” Stewart replies.

Their segment with Stewart ends with a hilarious pizza taste-test bit featuring some physical comedy beats that never would have worked in an audio medium. Later, Williams and Robinson end the episode with an exuberant dance-off that perfectly encapsulates just how happy they are to be doing exactly what they want on a much bigger stage.

It’s moments like those that ultimately make 2 Dope Queens work even better as a TV show than it does as a podcast. While many podcasts can provide a satisfyingly intimate experience, this one is best when it’s explosively visual. Getting to watch these performers as you would from a live audience offers a better appreciation for their comedic skills than could ever be enjoyed through earbuds alone.