Former death penalty attorney creates stand-up comedy show with inspiration from clients

Not long before his debut at the Edinburgh Festival Fringe in August, death row lawyer-turned-comic Josh Pickar spoke with one of his former clients. The man, who remains incarcerated and awaiting execution, knew the attorney was performing his stand-up show, Getting Off, at the festival and asked him to include one of his jokes.
Pickar thought it would fit because his show was about the death penalty.
The joke was about an inmate who visits the prison doctor because he can’t hear, and the physician prescribes him pills.
“Will this bring back my hearing?” the inmate asks.
“No,” the doctor says, “but it will make your farts louder.”
His audience laughs every time.
“People think it’s so funny that someone on death row wants me, during my death penalty show, to tell a very kind of juvenile fart joke, but it gets a huge reaction,” Pickar says.
Being a criminal defense attorney or a comic wasn’t always on Pickar’s radar. After graduating from the University of Chicago Law School in 2017 and earning a master’s degree in international relations from the University of Oxford the following year, he joined a large law firm in New York City. A friend there suggested he help with a pro bono death penalty case.
“I felt totally out of my depth,” says Pickar, 32. “I was like, my God, I’m going to meet somebody who’s been convicted of murder. What am I going to say to somebody like this? I’m just some gay Jewish kid from Boston.”
But with each new case, he began to realize he liked the people he was fighting for, regardless of what they did or didn’t do. At times, their meetings were lighter than he anticipated. He discovered his clients enjoyed laughing too.
“It was a really nice thing to be able to offer somebody, to have that humanity,” Pickar says. “So much of the relationship is figuring out who is this person, because that’s a large part of the mitigation story that you present.”
After roughly four years of practicing appellate law, Pickar started doing stand-up and improv with no intention of making it a career. Taking the stage and creating a set was simply fun, a stark contrast to his everyday work.
And yet, as much as he connected with his clients, he found comedy also allowed him to connect with his audience. That meant telling jokes about difficult topics like capital punishment. Just as his interactions with his clients changed his views on the death penalty, he hoped those watching his show might reconsider their own.
“My change around the death penalty, it wasn’t reading how many people are wrongfully executed that really had an impact on me. It was getting to know the people, feeling connected to them,” Pickar says. “I hope that in the same way the proximity changed me, that it might change other people too.”
After practicing as an attorney for seven years and doing stand-up for three, he decided to leave law and pursue comedy.
To do this, he went to another school, this one for clowns.
It’s called the École Philippe Gaulier, and it is a renowned French theater institution. Sacha Baron Cohen studied there. So did actress Rachel Weisz.
The school and its instructors helped Pickar, accustomed to preparing cases, become a performer who was more open and sensitive onstage. He found the less rehearsed he was, the more the audience connected with him.
Still, he used skills in comedy that he honed during his law career.
“I really felt like the experiences that I had had talking to clients in prison visitation rooms helped me in a lot of ways,” Pickar says. “Being able to sense what’s happening in the room and connect in the way that the person you’re serving is needing really helped me with listening and not being so rigid.”
He first put those techniques to work during his one-hour stand-up show at Edinburgh Festival Fringe.
Now Pickar is back in New York, considering other projects. He wants to create a musical with a former client about capital punishment. And once he connects with a literary agent, he’d like to write a book.
As for his Getting Off show, Pickar hopes to take it on tour to universities and law schools across the U.S. Students can ask questions and engage in a discussion about capital punishment.
They can also see firsthand the unexpected places a law degree can take them.
“Being a lawyer at a big law firm is not the only option,” he says. “A law degree is an amazing thing to have. You don’t know where it will lead, and you should take some chances and see what truly motivates you.”
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