Jeffrey Self on ‘Self-Sabotage,’ Sex Work, and His ‘30 Rock’ Secret

In 2009, Jeffrey Self got his first big break as an actor: a guest star spot on 30 Rock. He played Randy Lemon, the cousin to Tina Fey’s Liz, who visits New York City to experience life as an out gay man for the first time. In one memorable scene, Liz finds Randy passed out on the couch after a night on the town with “SLUT” written across his forehead.

“What the audience didn’t know was that I had gotten full-blown gonorrhea from a client, so I spent every moment of down time sneaking off to my dressing room to change underwear to avoid staining a sofa on NBC,” Self writes in Self-Sabotage, an upcoming book of essays about his life scheduled to publish in March. “That said, I was able to cross one item off my bucket list: ‘Film my first television appearance across from Tina Fey and James Franco, while having a leaking penis.’”

Self is an actor and author known for appearing in series like The Horror of Dolores Roach and Search Party, in addition to his memorable 30 Rock stint, as well as in movies like 2022’s poignant gay romance Spoiler Alert.

Self-Sabotage is Self’s life laid bare, in which he recounts his time growing up as a closeted gay teen in Georgia, escaping to New York City, and turning to sex work to help pay the bills while he attempted to break into the comedy and television worlds, alongside his then-comedy partner Cole Escola, who is now best known now for the smash Broadway production of Oh, Mary!.

The Daily Beast’s Obsessed has the exclusive reveal of the book’s cover image below:

In the book, Self also gets candid about a manic episode he had following the breakup with his first boyfriend, which unfolded publicly on social media, where he and his ex had made a name for themselves as boyfriend influencers. “My Fatal Attraction spirit animal had fled its cage and the brand that was our relationship was having an aggressive rebranding,” he writes.

It’s a collection of essays about, as its title suggests, self-sabotage, but also of resilience and personal growth. Trauma is recounted with scathing humor, and anecdotes are punctuated with paragraphs that double as therapy sessions: a clear-eyed look back at how the incidents impacted his life, the work he’s done to move past them, and what he’s learned about himself and mental health in the process.

Self now lives in the West Village with his husband, actor Augustus Prew, known for TV shows like The Lord of the Rings: The Rings of Power, The Morning Show, and Special. A sign that they had made the right move: On their first day on their new block, Sarah Jessica Parker walked by. “It felt so karmic and cosmic,” Self told The Daily Beat’s Obsessed. “I’ve since passed her so many times. It’s like seeing Minnie Mouse at Disneyland, her just walking around the West Village.”

We recently spoke with Self about his decision to be so candid about his past, whether or not he thinks talking publicly about his past sex work might affect his acting career, and the lessons he hopes people will take away from reading Self-Sabotage. (As well as the best places to visit in Palm Springs, our love of the movie Dicks: The Musical, and the 1989 PBS filmed recording of Into the Woods with Bernadette Peters and Joanna Gleason. Normal gay stuff.)

Self grew up in Georgia loving the personal essay style of writing from authors like David Sedaris, David Rakoff, and Augusten Burroughs. “I always imagined life experiences, whether they were less than ideal or traumatic, through the lens of, eventually, someday, this will make a good story,” he said.

There’s a difference, however, between the daunting process of writing those stories, and then realizing he’s going to have to be retelling them and reliving for the better part of a year while promoting a book. “So I’m going to be revisiting Memory Lane quite a bit,” he said. “Whether it’s a grimy, dirty street or a happy one, either way, I’m gonna be on it.”

The headline-making aspect of Self-Sabotage, by nature of our own perverted-by-way-of-Puritan curiosities, will be Self’s frank discussion of his decision to use sex work to pay bills when he was in his early twenties in New York. He talks about different experiences he had with different johns, the kinds of “tricks” he turned, and the various empowered and shameful ways it made him feel.

The chapter recounting his breakdown and the chaotic actions that led to his ex filing a restraining order against him is also told with a confessional vulnerability. Still, one has to wonder, did anyone in his life discourage him from telling those stories in a public forum?

“I mean, a history of sex work and a history of restraining orders doesn’t always equal booking a pilot next pilot season,” he said. “But those are things that have existed for a long time for myself, and at some point, I think you have to not be afraid of your past. Hopefully it can shed some light on those experiences that seem like a big deal to the average person, but really aren’t.”

And now that Self is starting to promote the book, the cover is revealed, and, soon, people will be reading it, does he have a goal for what Self-Sabotage—and sharing those stories about his life—might accomplish?

“I guess for Timothée Chalamet to play me in a movie,” he said, laughing.

“Some catharsis for my own selfish way of putting it all down [in writing],” he said, more seriously. “And I think there are lessons in it that help people of all ages as they navigate their own patterns of self-sabotage and hating themselves, because that has derailed so much of my life at every turn. Yes, I continuously have learned these lessons, which I document in this book. But I’m still doing it. I’m still self-sabotaging. I’m still self loathing. I’m still my own worst enemy. But I think that, by writing it down, I’m hoping to do better. And I’m hoping that it will encourage other people to do better and feel maybe less alone.”