Joe Skinner: You have so many different projects at any given time. Makes it very difficult for an interviewer to research. So, thank you. But I’m very curious like where you see the center of that Venn diagram.
Phoebe Robinson: Yeah, I think writing is sort of like the crux of everything. I’ve just always wrote when I was a kid, and I just loved reading books, and I really just, I think writing is so undervalued these days. I think, you know, people always make fun of like getting a humanities degree or like, “What’s the point of that?” It’s like, for the moment that we’re in now, because it’s all robots, and like nobody wants to think, and nobody wants to like engage critically with stuff, and it’s just like, “Let me go onto this like ChatGPT.” It’s like, “Just sit for five minutes, “and you could think it out yourself. “You could write it out yourself.” And so, I just think that writing and language and self-expression is so deeply just necessary to being a human being.
Joe Skinner (Narration): This is “Creative Spark,” and I’m your host Joe Skinner. And that was Phoebe Robinson, a multihyphenate stand-up comedian-writer, podcast host, and book publisher. Her publishing imprint, Tiny Reparations Books, just celebrated its five-year anniversary. But you might know her best as the creator and co-host of the podcast and HBO series, “2 Dope Queens.” Robinson has a new stand-up special out now on YouTube called, I Don’t Wanna Work Anymore,” where she takes a critical look at the millennial myth of the girl boss in hustle culture. In our conversation, we’ll talk about the convergence of art and commerce, our collective relationship to work, and how Phoebe writes her jokes.
Joe Skinner: Comedy is just like such a mystery to me. It just feels like alchemy. Like how do you do comedy? Explain it from step one.
Phoebe Robinson: It’s such a big question. I mean, I do understand that feeling because we were talking offline, and now we’re online, but I’m taking vocal lessons, and when I first started with my teacher Liam, who’s amazing, I was just like, singing just seems like magic. It’s just like, you know, like I’m like, I just never understood like how people were able to do it. And then you sort of like start learning like technique and sort of like the foundational stuff. So I started 2025… I started July, June or July of 2008, and I took a stand-up class at Carolines, which is no longer, but it was on on Broadway, and I didn’t really, like, I watched a few stand-up specials like Chris Rock or Wanda Sykes, but like I didn’t really understand stand-up in that way. And I remember like our first assignment was to like, by the end of the eight weeks, we had to do eight, sorry, no five minutes of stand-up, and we were all like, “We have to talk on stage for five minutes?” Like we were just so blown away ’cause that seems like, you know, two hours. And so we would just learn the process of like putting together a joke and being like, “What’s the topic area “you want to talk about?” Like learning to like stand in front of other people and tell a joke without shrinking or not having a confidence because one of the key things to stand-up is that the audience wants to have a good time, and they want to trust you, but if they sense that you are nervous or you’re scared, that makes them like tense up and not be able to enjoy it as well. So like you have to walk in there, not be overly arrogant, but just sort of like, “Hey, yeah. “I know I’m doing. We’re gonna have a good time. “Everything’s gonna be great.” It’s like when you get on a plane, and like the pilot, you just, you trust the pilot, and so, in that way, you’re sort of kind of dictating the energy of the room, and that is such a huge part of stand-up, but that takes so long to just trust yourself enough that like no matter what room you go into, who you’re following, you know, that you have a set of skills as Liam Neeson would say, a special set of skills, and you’re able to kind of just do it.
Joe Skinner: How long before you actually felt like you had a voice?
Phoebe Robinson: Typically people would say like around 10 years which I know sounds so long.
Joe Skinner: It does.
Phoebe Robinson: But it’s just kind of like with anything, because, in the beginning, you’re just sort of kind of emulating a little bit of who you’ve seen before and you like, and you’re like, “Oh I kind of want a little bit of this, or I want a little bit of the Margaret Cho. I want a little bit of like Janeane. I want a little bit of Bill Burr. And you sort of like are figuring out your voice, how to tell a joke, how to string jokes together, you know. To go from like five minutes to like now when I’m touring I do about like an hour, an hour and five minutes, like that journey of being able to sort of tell a story, like there’s so many things that go into it, and like learning how to do crowd work, not in the way that it’s done now which so much of it’s just for social media but genuinely interacting with the audience in a way that’s gonna like enhance your jokes and learning how to deal with drunk audiences. Like a late night Friday crowd is always like, “Okay, people got off work. “They had a bunch of drinks. “They came to dinner, “and then now they’re coming to a show at like 10:30.” You know that’s gonna be a little bit… You can’t necessarily just go through your entire hour without interruptions. Like you kind of have to make it feel more conversational and step out of your material and step back into it. So there’s all these things that you’re learning over the course of like 10 years that, even now, I’m at what? It’s, can I do math? What am I 17 years? There’s still shows where I go, “Oh, I’m unlocking this thing.” Or like, “Oh, I know how to do this thing.” And like the pure confidence that I can be like, “Okay I have a few ideas for jokes. “Let me do a workout show, “and I can sort of talk my way through “building out material.” Like I wouldn’t have been able to do that comfortably at like eight years, but now I’m just like, “Yeah, I’ll be fine.” Even if I only have like six ideas. Like the six ideas will take me like 20 minutes. Okay, great.
Joe Skinner: A lot of that sounds like very focused on performance, and you come from a writing background. So I’m curious how the two overlap.
Phoebe Robinson: I think what’s so great about stand-up is that a lot of times it’s about like distilling an idea down to like its essence and then building things on top. So typically my writing process is, and everyone is different, but I would do like workout shows in Brooklyn like either at like Union Hall or The Bell House, and I will sit down, and I’ll maybe have like five or six ideas and sort of like sketch like loosely like, “Okay, I think the purpose of this joke is X, “and that makes me think of Y. “Okay, so I can sort of link “like maybe these three bits together.” And then I’ll have like a couple of like punchlines I think can work within that. And then I’ll get on stage, and I sort of like talk through it, and, you know, this is sort of like I’ll have like the initial joke that like gets a laugh and that’ll make me think of something else. And then I, especially when I’m working on an hour, I open up a Google Doc. Is this really… And so I will put, especially like with stand-up, I try to think of it as like doing an hour, like three 20-minute chunks. So it’s like, this first 20 minutes like this is like the thesis of that. This next 20 minutes is a thesis of that. Third, whatever, and make sure there’s a through line through the whole hour. And so then I will go into my Google Doc. I will literally write, you know, “Untitled new hour,” and I will write out, “This is the thesis statement of.” and I am such a nerd,
Joe Skinner: Could you give me like an example of how a joke might evolve from that process? A specific joke.
Phoebe Robinson: Yes. So, okay. This hour that’s coming out, it’s called “I Don’t Wanna Work Anymore,” which I sort of thought about… I was thinking about this premise for a while because I used to be a workaholic, and then I just was like the girl boss, just like hustle, like everything, working all the time, yes, yes, sleigh queen, blah, blah, blah, and I was reaching a moment where I was like, “I’m just working all the time, and I don’t like this.” And I was texting my best friend. Her name is Karen, but she’s a good Karen, you guys, and she runs her own business. She has an interior design firm. And I was on a flight. It was like I did South by Southwest, and I was going to LA, then I was coming back to New York, and then I was going somewhere else, and I was like, “I don’t wanna write, “I don’t wanna work anymore. This is so annoying. “I should have just married like an old rich guy.” I sort of like built this whole hour around the idea of this like girl boss hustle culture being like the super badass feminist in a way that they like marketed it to us. It’s actually like not gonna set us free any more than just being like a trad wife is and sort of like trying to have to figure out like what works best for you. So then I had this whole… I had this bit about like Katharine McPhee. She’s married to David Foster, that songwriter guy, and I was on her Instagram, and it was her birthday, and she was on a yacht with her friends and David’s old ass, and I was like, “She has done life correctly.” She is on a yacht right now. He paid for all her friends, okay? And I am like, you know, flying premium economy to go like do stand-up somewhere, and I was like, “Oh, she rules.” And so I wrote a whole bit about their relationship.
When I’ve done this material, it’s resonated with a lot of people, not only because I think a lot of people are just feeling exhausted, and like they’re working, and they’re not getting ahead, but sort of this like, it felt very true to me, like as someone, me going, “I am a workaholic, “and I don’t wanna do this anymore.” I think people can sense the sort of the honesty in that. Writing can be so, like it’s real work, you know what I mean? It could be so hard ’cause you’re really trying to sort of pick your brain. And listening back to like my sets, I used to hate doing that ’cause I don’t particularly love the sound of my voice. And then I’m always like, “Oh well, I lived it, “so I don’t need to listen back to it.” But then like when you do, you can sort of hear. You could hear if you have too many words in a joke. You could hear when the audience is really responding to a joke, and you’re like, “Oh I can add something in here “to take it to another level.” You can hear when you kind of lose them a little bit, and so you want to like cut those moments out. So, yeah, I guess I just like homework.
Joe Skinner (Narration): Since her early days taking comedy classes at Carolines in 2008, Phoebe Robinson has navigated a career through some of the most dramatic shifts that the comedy world and the culture at large has ever seen. It’s easy to forget just how much has changed in those 17 years from the male-dominated alt comedy scene that was popular during the recession through the rise and fall of social media apps and the podcast boom to the culture wars over identity and cancel culture, and even with her own interviews with figures like First Lady Michelle Obama. When I spoke with Phoebe, I asked how she’s seen comedy evolve through all of that.
Joe Skinner: 17 years. It’s a long time to be doing a thing.
Phoebe Robinson: Yeah.
Joe Skinner: Anything. How has stand-up changed since you started?
Phoebe Robinson: I think when I started doing stand-up, I was 23 going on 24, and I was trying to figure out my voice, and, you know, I was always like funny, so I was like, “Oh, how can I put it in this format?” But then there was also that other part of that. I think I also needed/wanted the approval aspect of it. And I think that certainly was part of what was driving me in the beginning is getting that high of like, “Oh, I told jokes, and like people laughed “and like really enjoyed it.” And I think now at this point, I don’t need that. I like going on stage and making people laugh, and if I don’t have a good show… I always tell lines if I don’t have a good show. I go, “You know, these jokes will be killer one day. “They just weren’t for you.” And I’m like, and that’s okay ’cause it’s part of the process, and so I think where I’m at now is I am much more process oriented, and I think before I was much more results oriented, which I talked about in therapy. And I think with stand-up just being so consumed with like, “Gotta kill, gotta crush, “gotta have A material, every show has to be…” It’s like there’s no art form where you’re killing it all the time because otherwise what art are you doing? And so I think I allow myself to have shows that like weren’t that great, but I was able to figure something out, and it makes stand-up feel more like a 3D multidimensional thing as opposed to like, “Just gotta crush it,” ’cause you could crush it with garbage material. Like if you just wanna be super hacky, there’ll be an audience for that, and you can crush it every night, but it’s like you wanna do something that not only challenges you, helps you build a connection with the audience, but just the pure joy of like putting a joke together and being like, “Oh that joke is so good. “That joke is so good.” Like every hour I have like a couple where I’m like, “That joke is undeniable,” and the journey to get it to undeniable, I think is so exciting and invigorating, and I think that’s where I’m at now. And then that’s sort of like the micro view, and like the macro view stand-up right now, I don’t know. It’s very… I think social media has… It’s not my fave. And I think it’s kind of made stand-up like just with like the crowd work stuff where I’m just sort of like, I understand that, and I don’t begrudge that at all, but I think that that is not sort of the best that standup can be, and I think it creates this sort of sense of, sometimes you could tell an audience like they’re like, “Oh I wanna be a part of the show.” And I’m just always like, “You’re not, babe.” Like I’m here to write jokes. This isn’t so you can feel like you have a moment. And so I think people probably think that stand-up is much easier than it is, but I’m like, if you look at people like Ali Wong or Roy Wood Jr. or Ronnie Chieng or Bill Burr or Wanda or all those people, like there is so much that goes into the craft, and I think sometimes that is forgotten about because I mean, “Is that sexy, like the craft of it all?” Like you’re gonna go viral for the craft?
Joe Skinner: Right. Yeah, I mean I think a lot of our current media landscape really has a way of flattening art. I mean I come from a film background, so the same complaints are seen in film too, obviously. Like just a lot more small screen artwork being made ’cause people are forgetting how to make things for the big screen, and it’s, you know, it’s disappointing to see that kind of shift.
Phoebe Robinson: I think you’re totally right, and I think, for instance, this obsession with having to have a new hour every year. I’m like, “But you don’t need to have it.” You could take time off. You could live life a little bit. And it’s totally fine because I feel like if you’re just on that conveyor belt of, “Every year, I’m gonna have a new hour,” it’s like, okay, so January you’re starting fresh. Then you’re going on the road like in March, going on the road for a bit. Then you’re taping in the fall. And then, like I just am like, sometimes it’s just not enough time to develop something, and I think you can just kind of live life a little bit or take a breather. I understand that it’s a job, and you need to pay bills, but I think, I don’t think you can just pump out like, I don’t know, five, six hours in a row, and all of them are gonna be strong. I just don’t think there’s enough time for all of that.
Joe Skinner: Yeah, I mean anytime you marry art and commerce it gets really tricky, right? So I don’t know. I mean ’cause people have to make a living, like you said, and then, it’s funny though because with any art form, the thing that makes it good is often letting it sit and dwelling on it, and that’s why a lot of times I feel like the first thing somebody does can be amazing ’cause they had their whole life building up to it, and then that sophomore effort is like, “Okay, well you didn’t have as much time.”
Phoebe Robinson: Yeah.
Joe Skinner: But anyway, so that also kind of begs like a bigger sort of existential question for me, which is just, you know, what’s then sort of like your mission as an artist, as a comedian? What are you trying to do?
Phoebe Robinson: Ooh, I like that question. That’s great. You know, I think, A, I want everyone to feel good, have a great time, and B, you know, talk about things that I think have not necessarily have an impact on society, but sort of speak to those like larger issues like with this hour, “I don’t wanna work anymore.” Like obviously like I enjoy working, but I think sort of like it begs the question of like, “What exactly are we doing all of this for?” Like we’re so used to just running this race, but it’s like, “But why are we running the race, “and why are we doing this specific way?” So if I could make people laugh and think a little bit, I think that that is sort of, you know, the goal with stand-up.
Joe Skinner: But what do you think makes comedy so potent culturally? Obviously it still carries a lot of weight politically.
Phoebe Robinson: How much time do we have? You know, I think there’s a multitude of things. I think one, there’s an element of, especially if you’re doing like political comedy, like you know what Tina Fey was doing with like Sarah Palin or like sort of, you know, Chris Rock’s commentary on certain things in Black culture and beyond, I think there is an element that you can really, if you’re making people laugh, you’re making people listen, and maybe they will look at something differently because it doesn’t feel like a lecture. It doesn’t feel like, “You should be doing this, but you’re not.” You know, you’re sort of like couching it in something that feels cozy and enjoyable ’cause who doesn’t like to laugh? But I think there’s also a lot of sort of common denominator stuff, which I want us to sort of operate at kind of our highest version of ourselves, and I think sometimes with comedy, when it becomes so omnipresent, like anything, it’s sort of like, it’s like McDonald’s. Like you would go eat McDonald’s, but you’re not like, “This is the best that cuisine could be.” Like McDonald’s isn’t even cuisine, I don’t wanna get a lawsuit, but I think we’d all agree that McDonald’s is not cuisine, and sort of like we can really ask those challenging questions. We can really sort of explore life while also making people feel good and also having conversations about that. Like I think about like how Ali Wong’s special and how that really resonated with so many women who were like, “Yeah, this is sort of “what the experience life was for me being a mother,” And like for so long stand-up was just like the man on stage being like, “Ugh, my wife is so annoying.” And it’s like, “Oh, you mean she’s at home “raising the kids while you’re out doing this ? “Okay, that must be so hard for you “to be in a hotel away from your screaming kids. “Oh, oh my god. So hard.” But that really, I think made a lot of women feel seen in a way that they weren’t seen before. And I think that is what’s so special about stand-up is, you know, I think when Ali was writing that, I know her a little bit, I don’t think she was being like, “This is gonna be the voice of mother.” She was just really writing the most truest honest thoughts that she had about coming into motherhood and the way that she’s looked at versus the way that her ex-husband was looked at as a father, and like that just set off fireworks because I think that’s how a lot of people felt. And so I think there’s so much that’s great about comedy and stand-up comedy that can really drive conversations, and I think that we are in a tricky moment because if you are being funny, you can say things that are incendiary or that are unkind or heartless, but it’s comedy so it’s okay. And it’s like, well if nothing means anything, and everything is just for a laugh, then like what are we talking about? What are we actually thinking about things if everything is just a joke, ’cause there’s real power in comedy. I think a lot of people would agree with that. And so you have to be mindful of how you use that weapon.
Joe Skinner: Right, yeah, I mean I feel like that is like a fairly controversial topic. I’ve heard a lot of different takes from different comedians on it. Like should anything be fair game for a laugh?
Phoebe Robinson: And this is where I come back to the common denominator. It’s like, you could make that joke, but you could also do 30 other jokes that are way better than that piece of so why are you going towards that? You know what I mean? And so I think comics have to be honest ’cause you can’t have it both ways. You can’t be like, “I’m just a comedian. “I don’t know, I’m just saying silly things.” It’s like every comedian knows the power of words, like that’s part of the reason why we chose the job is that we’re standing on stage with a microphone, everyone else is shutting the up, and we are the ones sort of dictating the mood of the room for an hour. So if you do understand sort of the potency of the words that you’re choosing, then you know when you’re making a joke that is not cool, is not kosher. And so I think just accountability, to use therapy speak, we gotta have some accountability, you know?
Joe Skinner: Yeah. Well it sounds like if a comedian has bad politics, it sounds like you’re judging them for their bad work ethic in a lot of ways just for making bad jokes.
Phoebe Robinson: Yeah, and just sort of like, I feel there are so many things that you can talk about. There’s so many ways to look at stuff. Like if you look at someone like Brian Regan who could take like the smallest of things and run with it, and it is so funny. I just am always like, “Do you lack imagination? “Do you lack intelligence? “Do you lack sort of a curiosity,” which I think is probably one of the three tenets of being a stand-up comics is that you do have to have a huge sense of curiosity, where you will make a joke that you just shouldn’t be making in the first place and settling for that because it’s easy because you don’t wanna push yourself to do something harder? You know what I mean? Or push yourself to really dig deep into like, “What do I want to say on stage?” The fact that I’m charging people, they’re getting babysitters, they’re getting off work early, it’s a night out for them. Like, I wanna make this worth their time financially. So if you think about it in that way, I think it sort of pushes you to really have something to say or be really such a craftsperson at like making people laugh and feeling good and all those things, and, yeah, I do think sometimes I am a little bit like, “I don’t know about that work ethic “That seems kind of whack,” you know?
Joe Skinner: Why do you think comedians have a reputation for being mean-spirited sometimes?
Phoebe Robinson: Oh, you know, there’s a lot of unhealed, I think, with a lot of stand-ups. No, joking aside, I do think that there are some people who gravitate towards stand-up because, you know, they’re a class clown, they love making people laugh. Like that’s just sort of like, you know, I think everyone, when you’re growing up, you sort of gravitate towards a thing that gives you like positive like reinforcement. You know how like some people… Like a lot of people are smart, but if you’re not told that you’re so smart, like people will think that like, “Oh, I’m just kind of average, like don’t know anything.” And then you talk to them, and they’re smart. But like if you’re a person who can like get As in school and like, that’s how you get attention, then you’re like, “I’m gonna be like the straight A student.” And so you have some people who are like, “Oh, I get attention by being funny, “so I’ll go to stand-up comedy.” Some people are bullied, and then they feel like having a microphone and commanding a room is a way for them to sort of take back the power and own some of that. I do think there are some comics who, you know, are angry for just a multitude of reasons, and being able to take that out on others, especially if you’re funny, you really know how to be cutting. Like, you know, and not to throw astrology into it, but as someone who’s a Libra, one of a toxic Libra’s trait is that we know how to match your energy. So if you wanna start World War III, I will burn the down and say like the meanest things. And so I think sometimes there’s some of that, and I think a lot of times it has nothing to do with the outside people. It just has to do with maybe their self-loathing, or maybe they feel like they’ve been overlooked in life, and so they have a sense of bitterness that, you know, that like sort of that bitterness that sort of affects their personality. So I think it’s a multitude of reasons. And I think, for me, I don’t like that because especially we all know what it feels like to be made fun of and especially to be made fun of in front of other people and sort of the shame and the embarrassment, and your skin gets like a little hot, and you just like wanna shrink into your chair. So sometimes when I see stand-ups kind of picking on an audience member, I’m like, “You know how that feels. “You probably know how that feels the most. “So for you to then do that to someone else is so . so I have a strict like no policy. Like I don’t hang out with comics. Have no time. So not interested in it. It’s not nice. We should all feel good. You know, you’re making people laugh. Like that is like, this is a joy-filled job even though I made it very nerdy with all like my documents and whatever. But there’s such a like just happiness that can come from stand-up, and so when comics are mean to people, I’m sort of like, “That’s the opposite. “You’re supposed to spread joy.”
Joe Skinner: That’s great. I feel bad for asking a dour question to end on, but you spun it, you made it a good thing. So thank you for that.
Phoebe Robinson: Of course.
Joe Skinner: And thanks for coming in. I appreciate it.
Phoebe Robinson: My pleasure. This was so fun. I love your vibe. You’re just like so… Look at the glasses, the New York black. Like I’m here for all of it, so thanks for having me.
