What was the first job you had that felt like that?
It’s such a constant grind and my story’s the same as that of anyone who’s getting paid to write for TV. I definitely was able to use @officialseanpenn as a really cool boost in a lot of ways, but it really has been the same as any other artist. I did my own web series with my first roommate back in 2013, before Broad City turned into a TV show [from a web series]. I have been doing little projects like that for—I don’t want to say an embarrassingly long time—but yeah.
I would take any job, and I still will basically take any paid writing job. When my agents are sending my writing samples or a spec script to get me jobs, I will ask them not to lead with the fact that I’m @officialseanpenn, because I think it’s confusing to people to hear “Instagram comedy.” Like, if I heard that, I would be like, “Oh, like the Fat Jewish?” I’m not gonna say it’s been harder to get stuff going, but it’s definitely been this interesting interplay. It’s gotten my foot in the door with a lot of projects that I’m so grateful I worked on, but it is hard to unify everything. We’re all these multidimensional brands now. What I strive for is a world where I can just lead with my name and people are like, “Oh yeah, she’s an amazing comedian.”
I had a lot of jobs helping with my friends’ projects, but I think my first employed writing job was last year, writing for this Eric Andre project that he’s doing with Derrick Beckles for Adult Swim, called Mostly 4 Millennials. That was a short but really fulfilling moment in my life. For me, booking writing jobs has been so much more rewarding in terms of building my career than any amount of followers on @officialseanpenn. I’m obsessed with career longevity and making sure I have a career that’s beyond the internet.
On This Week Had Me Like, you talk about things that seem really ripe for making fun, but it doesn’t feel snarky. How did you find that tone?
Celebrity gossip is not known for being a warm, nuanced arena for discussion and empathy. It’s more just one-liners taking people down, but my love for bizarre pop culture is so deep. I don’t just sit at home and watch TMZ or Extra. It’s more like that underbelly, you know? I don’t care about Michael Jackson’s nose job, but I care about Michael Jackson’s pet chimp, Bubbles. I could look at pictures of Bubbles for days. I don’t know where that line is that I’m drawing, but my passion is so endless, and I think that’s why it comes off as not snarky, because I love. And of course, the other reason for the tone is Sarah. She was more involved in the podcast than a producer credit could describe. If I have nothing to say, I can just go to a snarky place, and Sarah has been really instrumental in shaping the whole tone to be different from everything else in pop culture commentary. I’m so grateful to her for her sensibilities and taste, because if I was in a vacuum, I don’t know what would happen.
With all this talk of longevity, is there anyone you look at and you’re like, “That’s the career trajectory I want”?
In terms of crossover, I think we’re all inspired by Cardi B and what she’s accomplished. And I really admire anyone making comedy in 2017, especially women. But my true blue heroes that I nourish in my soul and go to sleep thinking about and wake up wanting to be like? Howard Stern and Wendy Williams. They’re not as comedy-focused as me, but they’re outsiders that are engaged in the industry. They both came from radio, and they’re both these larger-than-life figures that are unapologetically themselves, and they have made a career of being over-the-top and outside of Hollywood but also in it at the same time. And Fran Lebowitz. Throw her in there. Unapologetic Jews are mostly my heroes, but Wendy also.
What advice would you give to someone who’s formulating a pitch in the hopes that they will get money and support to make a show, podcast, whatever?
I think we basically don’t know anything in this world. Don’t be afraid to ask for help, and find creative partners that you trust. I’m a really ego-driven, selfish person, and it’s hard for me to let go and share something with people, but that’s the place that I’m happiest, when I’m looking to people who are smarter than me and can just show me the ways of the world. I think it’s about not being afraid to look stupid.
I still put together decks [visual presentations] for projects that don’t go forward. It’s basically about doing it as much as you can, and it might not work out this time or the next time, but you’re learning as you go and becoming a better creator. When something inevitably pops off, you’re going to be armed with the tools that you gained from all your past failures.
And be yourself! We need more inspiring and specific voices out there, and I want more weird people to be creating things. Specific visions make the best art. I’m pitching a show right now, and my pitch was so watered down. My agents were like, “Girl, make this you! Get on this!” And then I just amped it up and injected it with that fabulous me-ness, and I’m like, oh my god, this is 800,000 times better. I gotta be me! ♦