Phoebe Robinson on the Legacy of ‘2 Dope Queens’ and the Future for Women in Comedy

Awards Daily’s Megan McLachlan interviews Phoebe Robinson, one half of 2 Dope Queens, about how to keep a fresh conversation, the end of the smash podcast, and why you won’t see more HBO episodes any time soon.

A No. 1 podcaster. A best-selling author. Comedienne Phoebe Robinson wears many hats—and occasionally majestic dresses, like on the “Regal AF” episode of the podcast-turned-HBO-series 2 Dope Queens. On the show, which aired its second season in 2019, Robinson and her fellow dope queen Jessica Williams interview celebrities, welcome unique talent, and have a blast on stage at Union Hall in Brooklyn.

I had a chance to chat with Robinson about how she keeps the conversation fun on stage, whether it’s harder to do stand-up alone or with a buddy, and why you won’t see any new 2 Dope Queens HBO episodes any time soon.

Awards Daily:  You grew up in Cleveland. I’m from Pittsburgh! Do you ever find that a Midwestern perspective comes through in your comedy?

Phoebe Robinson: It might just be the way that I approach comedy. I try to be open and allow things to surprise me and really just want to connect. With 2 Dope Queens, that’s not only evident with my relationship with Jessica [Williams], where we have this really great rapport, but also when we do the interview segments. There’s an element of curiosity and wanting to relate and make everyone shine. I think that’s definitely a Midwestern quality.

AD: I would agree with that. I love your questions and interviews. As somebody who interviews people myself, I sometimes struggle with that. How do you keep questions and conversations sounding so fresh?

PR: Part of it is the setup of the show. It’s a party with your best girlfriend. We are the guide to the night. Most of the guests we have on, this might be our only chance to ever interview them. This is our one shot. We want to make it fun and memorable. Being on the other side of being interviewed, so many times you’re supposed to push a product or market something well, so you’re in your head about doing a good job, making the network or the film studio happy. Jess and I really want to approach interviews where our guests are coming in not feeling like they have to sell their latest movie and can unwind and relax and have fun with us. That’s not only reflected in our questions, but also in the games that we do. For example, when we had Lupita [Nyong’o] on, we did a hair-braiding contest. No one’s done that with her, so we put her in her comfort zone with something she’s an expert at. It’s really nice where you can get a guest feeling like they are in control. It lets them put their guard down.

AD: What were some of the challenges to bringing your podcast to the live stage? I’m sure there were a ton.

PR: What was really great about HBO was when Jess and I went in to pitch the show, they were aware of the podcast, and some of the people who worked at HBO listened to the podcast. Nina Rosenstein [Senior Vice President at HBO] who we sat down with said she didn’t want us to change the magic that works on the podcast. It was great that they had faith and the belief in us to make the transition and keep the essence of what makes 2 Dope Queens work. Also, it’s the big leagues. Getting on HBO for comedy was a big deal. Jessica and I in Season 1 probably had less fun, just because we were so focused on making things right. Season 2, once we got the warm reception from people who watch the show and HBO being very happy, it allowed Jess and I to relax a little bit. Once we got out of our heads and trusted the process, it made it a much more seamless process than we thought it was going to be.

AD: I know the 2 Dope Queens podcast has ended, but how do you envision its legacy living on? You’ve done a lot for conversations around race, sex, and politics.

PR: I think there will be people who discover it in the months and years to come. The main reason why Jess and I started the show was because we knew so many funny women and people of color and queer people and they weren’t really being welcomed into that space or being nurtured in the way we thought they should have been. So hopefully what lives on with 2 Dope Queens, beyond the podcast, is that it encourages people to not only look outside of the normal avenues to find talent, but it also shows that you don’t have to wait for someone else to give you permission or to say yes to yourself, to create something organic and something that means something to you. We were very proactive about it. We certainly didn’t go into it thinking it was going to be on HBO. We just wanted to do something fun that we felt good about and was celebratory of funny people around us. If you just bet on yourself, you never know where you can end up by doing that.

AD: Do you prefer stand-up alone or stand-up with a buddy? Is one harder or easier than the other?

PR: I think what Jess and I do is less stand-up and more storytelling. I was doing stand-up for six and a half years before Jess and I met. I really love stand-up and I’m back into doing it now. It’s really nice to have an idea, write something, and get on stage and perform it and then tweak it. I don’t want to say I like one more than the other; I just really like creating, whether it’s by myself or with somebody who is really funny and awesome. I welcome all opportunities for it.

AD: Women are really having an impact in comedy right now, with Lilly Singh becoming the first woman to have a late show on a broadcast network. What do you make of this swell and how close are we to having a woman Tonight Show host?

PR: I think it’s really cool that the marketplace is wider and with more options and more room for different kinds of voices to be in there. I can’t predict how close we are to a woman hosting The Tonight Show, but I think things are going in the right direction. As long as everyone has the opportunity, I think that’s the best thing. Maybe it’s not necessarily The Tonight Show but some other thing that maybe some woman or person of color will create that will be the next evolution in the late-night show.

AD: You do comedy. You write. You act. What would you like to get into next?

PR: I definitely would like to do more producing and highlight other voices. As much as I love being in front of the camera, I also love just being behind the scenes and creating something. I eventually would like to get into directing. Whatever is new and something that I’m not strong at and have to teach myself how to do, I think that’s intriguing to me. Also, I’d also love to have my own publishing imprint.

AD: Finally, while the podcast is over, will 2 Dope Queens come back to HBO?

PR: The byproduct of doing 2 Dope Queens is that it really opened up a lot of doors for us that we didn’t necessarily foresee happening when we started. We’re both doing movies now. I’m doing a stand-up tour which starts in June (“Sorry, Harriet Tubman” Tour). She’s shooting a TV show and she’s doing the next Fantastic Beasts movie later on this year. We really got to a place where it was an embarrassment of riches. We’re realizing we’re really slammed right now and we don’t want to put out a crappy product. I’m always open to do another batch of episodes when things calm down a little bit. It’s so fun and we have such good people on the show, in front of the camera and behind the camera. Right now, we’re just too dang busy!

AD: 2 Dope Queens, too dang busy!

Catch Phoebe Robinson on tour in 2019. Visit her website for more info.