Interview with Josh Pickar

Few performers arrive at the Edinburgh Fringe with a journey quite like Josh Pickar's. A former death penalty defence lawyer turned comedian and storyteller, Pickar brings Getting Off  to the Fringe with a unique blend of humour, vulnerability and lived experience. I caught up with Josh Pickar to discuss his remarkable career change, finding comedy in unexpected places, and using theatre to explore some of life's most complex questions.

How was your journey from death penalty lawyer to comedian?

Fall 2025 was the first time in nearly a decade that I didn’t have a client in prison. I felt both enormous relief and real sadness because I loved that work. But in general, the transition has been less bumpy than you might expect. I did my first open mic about five years ago, then started improv soon after. At first, it was really just for fun, a light counterweight to the heavy work. Then I went to clown school at École Philippe Gaulier outside Paris, and that’s when I really felt like a performer for the first time. Blending those performance skills with a subject I’d spent years thinking about has made the transition feel surprisingly natural.

At what point did you realise comedy might become part of your life?

I’ve always loved making people laugh and used humor to make a point. Even while working as a lawyer, I joked with clients about myself because I could see how that built trust. After a few months of doing open mics, I nervously started doing some jokes about the death penalty, because it was already what I was thinking most about. I was surprised by how positively audiences responded. They engaged with it in a way I’d never experienced in ordinary conversation, and that made me want to see how far I could take it.

How much of Getting Off is drawn from real experiences?

All of it! There were more than enough true stories to draw from. Some details have been compressed or slightly altered for storytelling, but the material is all true. The hardest part was deciding what belonged and how to thread it together.

How do you balance serious subject matter with humour?

It takes time to figure out the right tonal balance, because I don’t want to make light of anyone’s suffering. But serious subjects are often full of absurdity. It’s funny seeing ordinary people navigate impossible situations. My clients teased me and I teased them. I’m a gay Jewish guy from New York sitting in prison visitation rooms with people from completely different walks of life. Watching us slowly figure each other out was often genuinely funny.

What challenges came with turning your experiences into comedy?

The biggest challenge was figuring out how much to explain. As a lawyer, you’re trained to anticipate every possible objection. If I did that onstage, the audience would rightly be so annoyed. But I also don’t want people to feel lost, because there’s a lot that non-lawyers wouldn’t know. I’ve spent a lot of time fine-tuning the balance so that we can get to the interesting stuff without too much friction.

Do you see similarities between law and performance?

The similarities that surprised me most were between stand-up and meeting with clients. Both require you to read the room and adjust in real time. Some days, clients wanted to go deep; other days, they just wanted a friend. I learned to set aside my prepared questions when a client needed something different from what I’d come to do. The most important moments often happened when I stopped trying to steer and just listened. On stage, just like in the prison visitation room, the key is knowing when to stick to the plan and when to throw it out.

What has surprised you most during the show's development?

I’ve been surprised by how willing audiences are to sit with uncertainty. I expected people to want the show to tell them what to think. Instead, they’re excited to wrestle with the questions themselves.

How do you approach writing material from such intense experiences?

The work was intense, but it was also fascinating and meaningful. I loved meeting people I otherwise never would have met, and I found a lot of joy and wonder in that. I was only 24 when I started, and I approached it with real curiosity and very little certainty. I want audiences to feel some of that curiosity without being overwhelmed by the heaviness. It’s a world that people live in, and it contains both profound humanity and deep difficulty.

Has creating the show changed your relationship with those experiences?

In some ways yes and in others no. It was my life for seven years, so after a while it became strangely routine. It’s only with some distance that I’ve realized how emotionally demanding it was and how it changed me in ways I couldn’t see while I was living it. I’m still figuring that out.

Ironically, trying to make people laugh helped me understand that period of my life. For years, every conversation felt like it carried enormous consequences. Now I’m in a room where the stakes are comparatively low. That contrast has helped me understand both experiences more clearly. But I don’t think I’ve finished making sense of it yet.

Why do you think humour helps us process difficult subjects?

We often laugh when we feel something is off, even if we can’t articulate why. Comedy gives people permission to stay with that feeling a little longer before deciding what they think. In discussing a system as unnatural and absurd as the death penalty, that’s incredibly useful.

What excites you most about bringing the show to Edinburgh?

It’s my first Fringe, so I’m really excited to experience the whole thing! There’s something wonderful about a festival where people spend all day hopping from venue to venue and discovering new work. It feels like the perfect place to debut a show that’s trying to balance comedy with questions that don’t have tidy answers.

What do you hope people are still thinking about on the journey home?

I hope they’re feeling curious. Even after thinking about the death penalty for this long, I don’t have all the answers. My goal is to show how wide the blast radius of the death penalty is—how its existence affects more people than we usually imagine. If people leave a little less certain and a little more curious about the lives of the people they’ve met over the course of the show, I’ll feel like I’ve done my job.

Equal parts hilarious and thought-provoking, Getting Off promises audiences a show unlike any other at this year's Fringe. I would like to thank Josh Pickar for sharing his extraordinary story with me. Josh Pickar: Getting Off is at Assembly – Roxy - Snug at 7:40pm from the 5th – 30th August (not 17th). More information can be found via the official Fringe website.