In her latest book, Please Don’t Sit on My Bed in Your Outside Clothes, Phoebe Robinson insists that 2020 was supposed to be her year. Well, we all know how that turned out. But the comedian, author, actor, podcaster, producer and publisher is certainly making up for lost time in 2021. Along with the new collection of essays (her third since 2016), there was her Comedy Central show Doing the Most with Phoebe Robinson on which she explored random skills and hobbies like archery and parenting with celebrity guests like Gabrielle Union and Kevin Bacon. She also launched Tiny Reparations Books, a publishing imprint dedicated to diverse authors. And late last month Freeform announced that she will executive producer, write and star in a series based on her second book Everything Is Trash, But It’s Okay.
On top of all that, there’s her first-ever solo stand-up special, I’m Sorry, Harriet Tubman, for HBO Max. In the hour-long set, Robinson gives us a crash course in what it was like quarantining with her British boyfriend and why Michelle Obama was responsible for the greatest night of her life. On a recent Zoom call, GRAZIA chatted with Robinson about returning to stand-up after a pandemic-induced break, building her Tiny Reparations empire, and why she’s never doing a ropes course with Kevin Bacon ever again.
So, wait, why do you owe Harriet Tubman an apology?
Yeah, it’s just because of, you know, the subject matter of the special. I talk about dating my boyfriend and our sex life. So, I’m just going, Harriet, I don’t know if it was worth it for you to be so good at navigation if this is what I’m doing.
This is your first-ever solo stand-up special. I’m sure that’s something you’ve been kind of dreaming about since you started comedy. How does the reality compare to what you envisioned when you were starting out?
It’s so exciting. I’ve been doing stand-up for 13 years, and my goals were to do a set on Letterman, but I think I started too late to do that; to have a half-hour Comedy Central special — didn’t get that. And then to have a one-hour HBO special. And, you know, I’m in the same category as Bill Burr, Wanda Sykes, Margaret Cho and all those folks. So, it feels surreal and it feels really exciting and I’m just sort of like, I did it! I can’t believe I did it!
What was it like getting back onstage and doing comedy in front of an audience again after, what, 18 months?
I stopped doing stand-up around the end of February 2020. And then, my run-up tour to the special started June of this year. So, what’s that? Like 15 months? That’s a significant amount of time, and I think up until that point, the longest I’d ever gone without doing stand-up was, like, over Christmas holidays. So, maybe two weeks. So, I didn’t realize until I had the time off just how much I needed a break from the hustle and grind of 13 years of doing stand-up. And when I got back to it, it was just really nice because everyone was excited to leave their houses again and have fun. I think everyone is just in the mood to laugh and have a good time. I think I came back to audiences that were phenomenal and really game. I think a lot of comics are the same, we lucked out to have a community that was so amped to have fun again.
I guess every stand-up set is a time capsule of that moment in which it was performed. But with a special like this, obviously it will live on. When you were putting together your set for Harriet Tubman, how did you think about balancing speaking to this very specific 2021 moment and performing jokes that would stand the test of time?
I started working on this set…probably in 2018, because I was supposed to originally shoot the special in 2020 at the Vic Theater. And, obviously, COVID made that not happen. So, I had been working on the set for a while between Doing the Most and working on other projects. So, for me, the special was never something that was going to be born out of COVID. I just wanted to have sort of evergreen material. And, of course, coming out of quarantine, I wanted to just update it a little bit and make sure that there’s some stuff that feels still timely, but is not too tied to the COVID of it all.
You’ve also just published your third book. I’m curious about your writing process. How do you decide which subjects and jokes are right for an essay and which go into a stand-up set?
With stand-up, you’re just more aware of the rhythm. You want to make sure there are enough beats where people are laughing every 20 seconds or whatever your standard is for however many laughs you want. Whereas with a book, it’s just sort of like, Can I dig deep and go off on tangents and play with levels and emotions? So, that really determines what goes where.
So much of the press around your new book is about you being a boss. But the chapter of the book about your Tiny Reparations empire makes it seem like you’re a little ambivalent about the role.
I don’t know if it’s necessarily that I’m ambivalent about it. But I think there’s just two sides of me. One side is really hard-working, has a strong work ethic, and really likes to create. And then there’s the other side of me that really just wants to lay in bed and watch Real Housewives of Potomac. I think everyone contains that level of duality when it comes to certain things. So, for me it’s sort of trying to just acknowledge that, yes, I’m going to be exhausted a lot, but also reprioritizing things to the point where I’m not just constantly working all the time and not enjoying my live or resting. I really do enjoy being a leader and collaborating with others. It definitely can be stressful sometimes, like anyone running their own business. But I’m so proud of the work that myself and my employees are doing. Every time we developed a show and it didn’t get greenlit or it didn’t sell — all those nos, and then we get the yes for my TV show Everything’s Trash. You just sort of go, Ok, all the hard work is paying off.
You’re also adapting your second book, Everything Is Trash, But It’s Okay, as a sit-com. What’s it like adapting an essay collection into a narrative show?
I’m really excited. We start the writers room soon, and so I think what’s great about having the book is we can pull storylines and beats from it and really expand it and fictionalize things, and really just have a great foundation for the show for us to work off of. So, I’m really excited about this process. This is the first time I’m adapting something to TV, so I’m gonna be learning as I go. But I’m in really good hands. Freeform is super supportive, so I can’t think of a better place to make my TV dreams come true.
You’re starring in the show, and I assume you’re playing a fictional version of yourself. Obviously, as a stand-up, you perform a version of yourself as well. But I wanted to know what it’s like for you to turn yourself into a fictional character.
I don’t know how it is for other people, but for me, this is fun. I get to play. We all call her “TV Phoebe,” and so we just kinda know that we can have fun and extrapolate on certain things and it’s not really related to me. So, it kind of allows me to live, maybe, a more hectic version than who I really am. I’m looking forward to it. I’m sure I will probably, like in Season 2 or Season 3, be like, I wish I didn’t name her after me so there could be a little more separation… [Laughs]
Did you stick with any of the hobbies you learned on Doing the Most?
[Laughs] Outside of doing a little bit of baking, that’s kind of the only one. The Kevin Bacon episode with the high ropes course — I was already terrified of heights, and so after we shot that, I was like, “I absolutely will not do anything scary like that again.” It was just too much. I was like, “It’ll be so funny, I’ll just be scared a little bit.” And then I was scared a lot! [Laughs] I was like, Whoops!
But, I see Whitney Cummings from time to time, so next time I’m in LA I wanna go back to that barn and ride her horse again. Because that was really cool.
