A former death row lawyer, Josh Pickar, explains how humour became central to his work defending men on Alabama and federal death rows, and why he now performs standup comedy about capital punishment. He argues that jokes shared with clients did more to humanise them than legal arguments or moral philosophy ever could, since the death penalty relies on keeping condemned people abstract, and laughter made that distance impossible to sustain.

Pickar, who spent seven years as a death-penalty lawyer after joining pro bono cases straight out of law school, recounts moments including a client's blunt response to him coming out as gay, and another who mailed him a prison mindfulness pamphlet annotated "NOT WORKING!" after a suicide attempt. He also describes uncovering misleading prosecution evidence, a supposed surveillance video that was actually a misleading slideshow of stills. He says the immediacy of standup, where an audience can reject a joke instantly rather than a court taking months to rule, drew him from law towards comedy as a new way to keep people engaged with an uncomfortable subject.