As I come to terms with the fact that I am a comedy buff, and my snide disdain for 90% of comedians turns into less of a shield from that fact and more of a demonstration of it, I’d like to expand this column with that. While I will stay primarily a music critic, artists will draw inspiration across mediums and limiting myself to discussing music limits my writing in a way unfair to the reader as well as myself. When John Prine passed earlier this year, film critic Roger Ebert’s early review of one of his shows made the rounds and many wished Ebert had spent more time writing about art besides film, because he was just so good at it, and while I’m no Roger Ebert and Stanhope is no undiscovered gem like John Prine, I’d like to work on that principal.

First, this is not an entry point for Stanhope’s work. The book largely relies on an understanding of his persona and what glimpses into his life we’ve gotten from it. Emerging out of the Angry White Boy comedy style that came to prominence in the 90s and we’re still bogged down by, Stanhope always stood out to me as the only one of them who could find empathy in the material. If you’ve ever seen Bill Burr’s work, an angry man who scarcely finds the victim empathetic and usually gets laughs simply by saying words he’s been told not to, imagine Stanhope as the philosophical antithesis of Burr despite using many of the same mechanisms. His 2009 album From Across The Street is this at it’s finest, with an extensive seven minute routine about how he felt after a fan committed suicide after his show, and the regret he had for phoning in that performance. He doesn’t keep this levity in darkness away from him either, as demonstrated by this ten minute routine about his mother’s death which would become the way he could get a publishing deal for his first book, Digging Up Mother.

That said this empathy is not always what Stanhope fans enjoy from his work. A huge swath of them revel in his drug abuse and sexual escapades even as he tries to make them as unappealing as possible. The most dedicated Stanhope fans, who I’ve seen on Twitter and at the three live performances I’ve seen, idolize Doug in a way that baffles him and myself alike. They desperately wish they could live the absurd life he does, even as he repeatedly points out it’s awfulness.

Doug kind of has three personas: his stand up, his podcast, and his writing. His podcast stands in stark contrast to his stand up, as he struggles to keep up the unapologetic persona he has on stage once literally anyone else is sharing the mic. His writing in the last two books has been a fusion of the two, in part because his groundbreaking format or his audiobooks — part scripted memoir, part complementary perspectives through conversations recorded and put directly in the audiobook, and occasional goofs around the very format of an audiobook — has been a simple fusion of his stand up and his podcast. This book stands apart from all three though.

This book is like listening to Stanhope be in therapy. Plenty of performers have been fairly open about using their art and performance of it as a way to process emotions — why pay 100 bucks to see a psychologist when you can get paid 100 bucks for saying it all on a stage — but this book is when the levity largely breaks down. After his 2016, a year so absurdly disastrous for him the election was an afterthought, he had a wakeup call. The way he’d embraced sex, drugs, and insanity was starting to fall down on him in devastating ways. To say he was “getting too old for it” is a cliche he would hate even more than I do, but his adventures and parties and escapades had become numbness to him. There was no drug that he was so addicted to that it ruined his life (there is no question that he’s an alcoholic but at this point people around him want him drunk) but rather the larger lifestyle of six day parties riddled with intoxicants and infidelity had ceased to bring any sort of pleasure and was starting to destroy the lives of people around him, most notably his wife-out-of-wedlock Bingo. Nights he couldn’t remember were nothing new, but after so many years of that life the number of nights that would fade into obscurity simply because it had become monotonous was growing.

He lays this all bare in his third book, No Encre For The Donkey. Perhaps the perfect companion piece to This Is Not Fame, his second book that copied the format of Digging Up Mother but with the substance merely being crazy stories from his life in comedy, this is the dark underside of his life that he has felt compelled to mute until now. It’s unfair to say that he was using humor to hide from his pain — he rants about that saying in the book and elaborates on how humor helps him face the pain — but there is some way in which he hadn’t faced the pain like this before publicly. He’d always tempered the horrific events with punchlines, in part because it helped him say it and in part because it helped us hear it. But now he’s reached a point where he needs to express all this agony. There are jokes in this book but as it progresses they get fewer and further between, and the ones that are there feel more like a way for you to keep reading without crying.

If this all sounds compelling to you, but you do not have familiarity with Stanhope, I do need to emphasize I do not recommend starting with this book. I have provided much more context in this article than the book itself provides. No Encore For The Donkey won’t have this effect if you’re new to the Doug Stanhope brand and style. It’s a fascinating new step in the context of his broader work, necessary reading for anyone who has listened to more than two or three Stanhope albums, but completely inaccessible in its power to any outsider.

No Encore For The Donkey is available on Audible exclusively now.

Elizabeth von Teig is a musician and author living in Brighton, Massachusetts. Her expertise is classic rock, folk punk, and the blues.