Ever since a chance meeting in 2014, Jessica Williams and Phoebe Robinson have taken their collaborative friendship to higher and higher heights. Their “2 Dope Queens” show, featuring stand-up sets from talented friends, became a popular WNYC podcast and toured the country. In February 2018, that podcast became a series of HBO comedy specials, filmed in Brooklyn’s vaunted Kings Theatre, which seats thousands.
The second season of “2 Dope Queens” premieres on Friday, with a new futuristic set and celebrity guests like Lupita Nyong’o and Keegan-Michael Key. On Dec. 5, the morning after taping Key’s episode (“Regal AF”), Williams and Robinson hosted a celebratory brunch in partnership with Girls Write Now, a New York-based non-profit that pairs underserved girls with engaged mentors, to talk about everything from creating the show to honing their self-care routines. Later, they sat down with Variety to discuss coming back to HBO for seconds.
For the second batch of specials, what did you want to change or adjust from the way you did things the first time? How does the elaborate new set play into that?
Phoebe Robinson: I think whenever you do the first season of something, you’re so precious about it. You just want to make sure you’re doing your job and executing it well. So with season 2 we were like, “we can have more fun with this and play with it.” We got on the phone with [production designer] Michael Krantz to tell him what we were thinking about, and he put it all together. If someone had said all the ideas we had [to me]…it’d be like, a stick figure on a Post-It. So he really killed it.
And our show is a variety show. It’s a throwback to like, Sonny and Cher…so we wanted to have that element play into it a little bit more for it to be our modern take on that.
Jessica Williams: We have a very specific thing that we like to do, and we wanted to do that, but tighter. Anything we had learned in the previous year, we assess and make sure that we run a tighter ship. But for the most part, we like the show [as is], and we just want to keep doing it.
You do a really impressive job of doing the show as it was originally, but now in a giant space for HBO. How did you talk about making that work?
Robinson: HBO really gets our vision and our voice, and they really loved the podcast, so they were like, “don’t change it.” I think [at first] we felt like we had to do all these different things, but they were like, “what works is this magic between you, and having the different comics on, and having the celebrity interviews feel like you’re going to get to know someone in a way you wouldn’t anywhere else.” It’s sort of like, if it ain’t broke, don’t fix it. Which is a testament to HBO. They’re smart enough to realize that if something has magic in it, you don’t really touch it. You just let it shine.
You’ve also talked a lot about bringing comics in who might not have been able to do that on another show. What makes someone a really good fit for “2 Dope Queens”?
Robinson: Everyone who’s featured in both seasons, I’ve done tons of shows with. But the general barometer is that they have to be inclusive, they can’t punch down, they have to have a really unique point of view. And like, they just have to be fuckin’ funny. At the end of the day, it’s funny first, and if you can kill it and make people laugh, great.
And what about for your celebrity guests? I always like to talk to people about how they interview because it always seems like it’s just a conversation, but it isn’t quite.
Williams: [Interviewing] is one of those things that seems easy when it’s done well. But it’s hard! We try to have people of all orientations, genders, races. Period. We want to see melanin all throughout the show. So we try to find people who are interesting, but also people that we talk about. We talk a lot about pop culture on our podcast, and there are certain people that just come up.
And we’re always really excited to be able to get people that want to come play, too. Especially for this round of specials, we have a really good variety of guests, and I think every single one is going to be interesting. And we do play games with them too, to get us all out of our heads and get a little loose. Celebrities have to do interviews all the time, and we hope with “2 Dope Queens,” we can get to know [them] in a new way.
Robinson: Interviewing is so hard. Like, I love doing it, but it is so hard. It’s like my homework. But it is cool to read about someone’s life. You always find out something new or interesting about them and it’s like, “oh, I didn’t know that! Let’s talk about that!” A lot of times I think we just sort of latch onto the five famous things you know about a person, but people are just so much more interesting than a resume or summary of their lives. I like digging into that. People’s Instagrams are really great for that…and shoutout to Wikipedia, you can always find fun facts. [laughs]
What’s something that you’re particularly proud of that you don’t think you could have done without “2 Dope Queens,” either personally or professionally?
Williams: “2 Dope Queens” really encouraged me to speak out more, actually. Strengthening my voice. I don’t think I would’ve been able to do that without “2 Dope Queens.” It makes me a lot more playful, and now I get to exercise that muscle a lot.
Robinson: I’ve gotten to meet a lot of people that inspire me. And I feel like I really try to learn a lot from other people, especially my heroes. So getting to, for instance, have a moment with Michelle Obama, read about her book and see her life…everyone is evolving. I don’t care how famous you are, how big a humanitarian you are, [you can still make] that human connection. It takes them off of that pedestal a bit, so you’re not just like, “I can’t imagine being in this room with that person.”
We can now feel more confident about ourselves…and we can also sort of relax and realize it’s all part of an ongoing process. You’re always figuring out how to be better, smarter, stronger. It’s cool to recognize that, and to use that, and to figure out how to live your own life in a better way.