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Phoebe Robinson on her Comedy Special, Book Release, and Starting a Publishing Imprint, Tiny Reparations

by Jamia Wilson

While everyone else was slowed down by COVID, comedian, bestselling author, producer, and actor Phoebe Robinson was busy taking over the world. Between her HBO Max special, her production company, and her third book marking the debut of her new imprint, Robinson is making big moves and bringing other marginalized creators with her.

Since the COVID-19 pandemic limited everyone’s ability to assemble in person, I initially met Phoebe Robinson on a rainy evening last March at a Zoom Happy Hour. Robinson was both hosting and celebrating with other executive editors and publishers of color who, including Robinson, had been featured in the New York Magazine article, “Publishing’s New Power Club.” Everyone there knew that Robinson had been making headlines with her new Penguin Random House imprint, Tiny Reparations Books, and I had been profiled in the same piece for my new role as Executive Editor at Random House. We were there alongside a number of other honorees whom the publication describes as “a wave of [publishing] hires set to pick up where the reckoning left off.” 

That “reckoning” was the shift in the cultural zeitgeist that came in response to the police killing of George Floyd, and included widespread calls for greater diversity, representation, and inclusion at all levels of media. As a pop-cultural polymath, Robinson has long been amplifying BIPOC voices through her TV production company (also called Tiny Reparations) founded in 2019, her multiple podcasts and interview shows, her HBO specials, and her prolific work as a comedian, writer, and actor. Her imprint is just one recent example of Robinson’s voice becoming in ever-increasing demand—and she’s more than ready to deliver the goods, and to bring others with her.

Six months after our first encounter, we meet up over Zoom again for this cover story and the interview feels auspiciously timed. Robinson is just weeks away from her 37th birthday, her third book release, and the premiere of her HBO Max standup special. With two well-stocked, color-coordinated bookshelves as her backdrop, she expresses empathy for emerging creatives with similar ambitions. “I remember when I wanted to write a book, I had no idea how to break into publishing,” she reflects. “I didn’t know how to get an agent. I didn’t know about contracts, all this stuff that you’re just not educated about. People don’t tell you anything about how publishing works.” While inching closer to the computer screen to drive her points home, Robinson reveals her vision and strategy for supporting the diverse voices she aims to amplify in TV, books, comedy, and beyond. “I want them to be passionate about their work,” she says of her future collaborators, “but also, to be supplied with knowledge so they can handle the business side of things.” 

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You likely became familiar with Robinson through her Brooklyn-based comedy podcast 2 Dope Queens, which she co-hosted together with The Daily Show’s Jessica Williams from 2016 to 2018. The podcast was so popular—it rose to number one on iTunes the first week it was released—that HBO commissioned a 2 Dope Queens TV series. The show ran for two seasons, with eight episodes that followed the same format as the podcast, but with the added bonus of sets, lights, cool clothes, and very fancy wigs. In their hilariously relatable and binge-worthy podcasts and TV episodes, the pair used a mix of storytelling and standup to discuss a wide range of topics, including love and sex, race, pizza, New York, Black hair, Black nerdiness, bikini lines, Billy Joel, and other “sexy-ass content.” During these shows, the Queens also featured standup sets by their favorite women, queer, and BIPOC comedians (their podcast may have been the first place you heard Aparna Nancherla or Michelle Buteau), providing an influential platform that expanded the media landscape by amplifying marginalized talent. As with her other literary, television, and comedy pursuits, Robinson revealed herself to be an inclusive and intersectional innovator and collaborator, while also establishing her own singular voice and creative talents. 

“Comedy can change people’s opinions about things. It just absolutely can. You can wield power in the political arena [with comedy].”

Robinson mastered the art of podcasting, not only with 2 Dope Queens, but also with her subsequent interview program Sooo Many White Guys (2016-2020), and Black Frasier (2020), which she describes as “an interview-advice hybrid show hosted by a Black person who has never seen an episode of Frasier.” For the book arm of her growing media empire, Robinson partnered with Plume, the publisher of her essay collections You Can’t Touch My Hair: And Other Things I Still Have to Explain (2016), Everything Is Trash But It’s Okay (2018), and her Tiny Reparations debut, Please Don’t Sit On My Bed In Your Outside Clothes, which came out in September. Concurrent with those literary successes—which landed her on The New York Times Bestsellers List—Robinson also got her foot in Hollywood’s door with acting gigs in the films Ibiza (2018) and What Men Want (2019), and as a writer on TV shows—consulting on Season Three of Broad City and writing for Portlandia in 2018. Before shattering glass ceilings in comedy, publishing, podcasting, and producing, Robinson grew up with her accountant and entrepreneur parents, Phillip and Octavia, and her older brother, Democratic State Representative Phil Robinson, Jr., in the Cleveland suburbs of Northeast Ohio. After high school, she studied screenwriting at Pratt Institute in Brooklyn, which kicked off her long-time residency in New York City.

One of her first professional jobs out of college was writing for MTV’s hit talk show Girl Code, but Robinson says she really “developed her voice” by doing standup, which she started performing in 2008, and by writing her blog Blaria (aka Black Daria) which, in 2014, evolved into a monthly comedy night at UCB East, where she first started collaborating with Jessica Williams. “It was just about standup,” she says of her life at that time, “I just cared about that.”

Robinson’s intention was always more than just getting people to laugh, though. “I’ve been doing standup for 13 years and, you know, comedy can change people’s opinions about things. It just absolutely can,” she says. “Look at the way Sarah Palin’s whole persona was changed because of Tina Fey. Without a shadow of a doubt—you can wield power in the political arena [with comedy].”

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Robinson says her goals back then were to get a set on Letterman and to get her own HBO Comedy Special—the latter of which came to fruition in October when her first solo comedy special, Sorry, Harriet Tubman, premiered on HBO Max. Throughout the cleverly irreverent set, Robinson weaves through bits about civil rights films, Michelle Obama, interracial dating, reparations, therapy, bathroom humor, and more. “It feels so good to be out!” she exclaims to the cheering crowd gathered for the outdoor taping at the Brooklyn Botanic Garden. “It feels so good to be out…and away from my boyfriend!” she continues, poking fun at the white gent she frequently refers to in her comedy as “British Baekoff,” because he’s British and loves to bake. “I’m the Rosa Parks of the bedroom,” she jokes, because, while all her boyfriend wants is “for [her] to get on top” during sex, she’s “not getting up for any white man.” Reflecting on their time in lockdown, she says,  “I love my boyfriend, I do, but we quarantined for 15 months! Don’t nobody wanna live the Martin Scorsese cut of a relationship!”


 In real life, however, Robinson says the couple actually got closer during quarantine. “Prior to COVID, we were just traveling the world—he’s working on music, I’m doing standup comedy. So, it’s nice to sort of be in the same space. He’s my best friend, my partner-in-crime,” she says, adding, “In the beginning [of quarantine], we were baking so many cakes. Red velvet cake—I mean, super unhealthy. And then we were like, ‘OK. We have to slow down, because our sweatpants are getting tight!’” 

When I ask if she finds it difficult to write jokes during a time of tremendous loss and global upheaval, Robinson replies that audiences are craving opportunities to laugh now more than ever. “For the most part, while touring and then shooting the special, people were like, ‘Please. We want to feel joy and forget our problems,’ she explains. “It was nice that I could be the fun part of their day. I take that as a serious responsibility. People are getting out from work early, hiring babysitters, or asking their parents to come over to help watch the kids because they just want an hour where they can have a good time. So, with that knowledge, I want to make sure everyone is feeling good.”

Another thing Robinson did during the pandemic, she tells me, is read. A lot. “During COVID I read 60-something books. I was up every morning just reading. That was the one bit of normalcy I could control. Truly, reading helped me thrive.” When I ask if, out of all the books she read, any really stayed with her, she’s prepared to give me a thorough answer. “You know what?” she says. “I keep a list of the books that I’ve read. And it’s organized by year. So—I’m a lot! Let me pull it up in my Notes.” After scanning her phone screen for a bit, she lists off some of her favorites. “Of course, I love Sam Irby. She always makes me laugh, so I’m down to read any of her stuff. I really loved Jacqueline Woodson’s Red at the Bone—I think it was such a great book. And I also read Susan Cain’s Quiet: The Power of Introverts in a World That Won’t Stop Talking. After reading it, I was like, ‘Oh, yeah. I’m totally an introvert.’ Like, I like to perform and be on stage, but being around people also sucks my energy and I get very tired. I also loved Such a Fun Age. I’m obsessed with Kiley Reid, so I can’t wait to see what she does next.”

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With all this book talk, it was only natural for us to shift our focus to Robinson’s inspiration for starting Tiny Reparations Books, and how it all began with her own search for a publisher. “I remember when my lit agent and I were shopping my book around in 2015,” she says, “some editors were saying, ‘This book won’t sell. People don’t want to read funny essay collections from Black women. It’s not relatable.’ They just totally dismissed it.” Recalling her frustration around these reactions to her material at the time, she says, “In 2015, you’re telling me that nobody wants to read a book written by a Black woman?” When I ask how Robinson’s latest book is being received after all her subsequent success, she replies, “When my first book became a New York Times bestseller, people were like, ‘Oh my God! We would have loved to have published this book. Why didn’t you send it to us?’ And my agent said, ‘I did, and this is what you said.’”

Consequently, it was this experience navigating the publishing industry for the first time that motivated Robinson to start her own imprint. With Tiny Reparations, she aims to ensure that diverse voices have a better experience than the one she had six years ago. As a leader now in an industry where the number of book editors who self-identified as white was over 80 percent in 2019, Robinson is committed to expanding the publishing world, proudly launching upcoming debut titles by BIPOC authors Kai Harris, Grace Li, and the artist Tourmaline. “When I was starting Tiny Reparations Books, I wanted it to be a place [where I could say], ‘If I don’t end up publishing your work, it’s not going to be because of your race, your sex, your gender, or your identity.’ It’s just going to be because it’s not necessarily the right fit for me,” she explains. 

Robinson goes on to break down what she thinks the publishing industry needs to do in order to truly become more inclusive. “For one thing,” she says, “there needs to be an incubator system, whether that’s for budding writers, editors, or publicists. Because, as we know, [marketing] can be predominantly white, and if you’re not having people thinking of outlets that are for people of color, or for the queer community, then that’s—I don’t want to say ‘problematic’ because that word’s overused. But it’s a massive oversight that’s unacceptable at this point.”

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In addition to nurturing a greater diversity of writers, Robinson says she also wants to see a diversity of stories. “I cannot tell you how many slavery-themed manuscripts we are getting; how much Black trauma we’re getting,” she says. “I know there are authors who have other stories. College-educated Black women are the biggest readers in the country. To think that we wouldn’t want to read something light or uplifting or read an espionage book or read a romance or read about a family—it’s really ridiculous.”

Robinson says there’s also a problem with book reviewers that needs to be addressed. “The majority of the critics are straight, white dudes or straight, white women who may not really understand the nuances of different communities, or the stories they want to tell,” she says. “We need to look at the whole system from start to finish—how we promote books, who’s reviewing them, who’s reading them, who’s pushing certain books while not promoting others. That would go a long way towards changing things from how they are right now.”

Alongside her deep commitment to being the change she wants to see in the world, Robinson says she is equally invested in creating spaces for “quirky Black people, silly Blackness, and joyful Blackness.” Grinning, she elucidates her point with more context. “I think that there’s an expectation of Black women who do anti-racism work to just be miserable all the time,” she says. “We’re supposed to be ‘saving the world’ while everyone else is just out at brunch eating their avocado toast.” 

Rejecting this trope of Black women as rescuers and redeemers, Robinson instead embraces lighthearted defiance and laughter as pathways towards liberation. “It’s very interesting that Black women are expected to do the labor 24/7, in a way that white feminists are not,” she says. “They will post [on social media] when it’s fall and they’re in a pumpkin patch somewhere doing yoga and having fun. But Black women are not allowed to have fun. We have to do the business of saving everything.”

When I ask how she finds time for fun herself, with so many demands being placed upon her time and attention, Robinson reveals how she manages her very full schedule without burning out her creativity. “Setting boundaries, taking time off, and resting are just as important as creating and doing,” she says. “I never want to work from a place of busyness. Because that is just like, ‘Oh, I’m afraid to stop moving.’ When you’re available all the time, or you’re stepping into roles where you don’t necessarily need to step in, then you’re not allowing other people to flourish. I still work a lot, but you’ve got to have boundaries. I put my phone on silent sometimes and it’s great. If I miss your call, I’ll call you back. It’s fine.”

Robinson also makes sure to point out that although she has many projects, she focuses on the work that delights her and gives her a sense of purpose. “Starting from standup and then adding in podcasting and then adding in producing—as I’m getting stronger in each area, I feel like I can take on a little bit more, and that’s how I keep going. I try to have it make sense. I’m not going to start, I don’t know, a jewelry company. Because that would be like, ‘What? Bitch, why are you starting a jewelry company?’ I think my mission statement through it all is that I want to create places where women, people of color, and the queer community can get their work out there. If I’m doing that, I feel like I’m on the right track for myself.” 

I inform Robinson that she is so admired, even her pretend example of her supposedly off-the-wall, hypothetical jewelry company is probably viable. In fact, I would gladly pay good money for a “Don’t Touch My Hair” necklace. This makes us both erupt into laughter before Robinson concedes, “Good point!”

As we prepare to wrap up our interview, I ask her how she remains motivated to do so much work that often feels ahead of its time, and her answer is one that will stick with me. “I think we are taught to place too much emphasis on the outside ‘No’ rather than on ourselves,” she says. “If someone says ‘No’ to you, you don’t have to say ‘No’ to yourself. You can say ‘Yes’ to yourself. You can say, ‘I’m gonna go off and do my own thing.’ Because people always catch up. It may take a while, but people always catch up. And then you’ll be like, ‘Yeah, I knew I was the shit—thank you for finally realizing it!’”


PHOTOGRAPHED BY the tyler twins

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This article originally appeared in BUST’s Winter 2021/2022 print edition. Subscribe today!

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Founded in 1993, BUST is the inclusive feminist lifestyle trailblazer offering a unique mix of humor, female-focused entertainment, uncensored personal stories, and candid reporting that tells the truth about women’s lives.

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