Readers of comedian Gary Gulman’s memoir, Misfit: Growing Up Awkward in the ’80s, are strongly encouraged (by Gulman himself) to read the entire book. That includes the introduction. “Some people skip the intro,” he writes with the precocious use of language that is his trademark. “I don’t trust them. It makes me wonder where else they cut corners, where else they’re phoning it in, what other flimflammery they’re perpetrating.”

Misfit fulfills the comedy rule of three, coming after two recent specials that are benchmarks in Gulman’s more than 20-year career. The first, It’s About Time, (2016) contains two of Gulman’s signature jokes, a confrontation with an entitled shopper at Trader Joe’s and a summary of a faux documentary about the men and one woman who abbreviated all 50 states down to two letters. That joke went viral after Patton Oswalt posted about it on social media following Gulman’s now legendary performance of it on Conan. “Doing a TV spot about just ONE premise is beyond ballsy and very rare,” Oswalt wrote. “I’ve never even attempted it. @GaryGulman makes it look easy.”

The second was The Great Depresh (2019), his masterpiece thus far, and which chronicled his triumph over the debilitating depression that led to his hospitalization and electroconvulsive therapy treatments. Misfit, which is all new material, picks up during that period, when, after being blissfully married for only six months, “a sinister third wheel” in the form of “crippling depression and anxiety” subverted his life and career. On the advice of his psychiatrist, he moved back to his mother’s Massachusetts house at the age of 46. Returning to his childhood room triggers stories of, to quote the book’s subtitle, “growing up awkward in the ’80s” with his financially strapped single mother. (His parents were divorced when he was a preschooler).

Misfit spans kindergarten through high school and beyond, fraught years when, say, losing a library book could have the high stakes and drama of The Shawshank Redemption.

Gulman spoke with Vanity Fair about the books that inspired writing his first, the glory of Sesame Street’s Grover and Bugs Bunny’s Jewish energy.

Vanity Fair: The cliché expression is, “What I really want to do is direct.” For you, it was to write a book?

Gary Gulman: I had an idea for a book in 2015, but I got really sick, and I didn’t pursue it. After The Great Depresh aired, some publishers asked if I was interested in writing a book. I dusted off this outline, and there was some interest. It was before Zoom. I would tell these stories in meetings, and it was really fun. Those are my people. I love to talk books; I read three or four books at a time. It was a dream come true; not everybody’s dream, but my dream has always been to capture my ideas and stories in a book. I found that ultimately, I was more comfortable telling these stories in book form because I get very anxious onstage when I go too long without a laugh. With a book, you can really air out these stories that are very personal.

You mentioned being a voracious reader. Did you do a deliberate read of celebrity bios and memoirs before starting your own?

I read Steve Martin’s extraordinary Born Standing Up a couple of times and John McPhee’s book on Bill Bradley, (A Sense of Where You Are), which is really great. I also read a lot of books on memoir writing. Mary Karr wrote a great one (The Art of Memoir). Another one that was really helpful was Kurt Vonnegut’s Pity the Reader, a collection of speeches he made and things about being a writer. And then I reread for the dozenth time George Orwell’s six rules for writing, which was really helpful in avoiding cliché. Ultimately, reading became procrastination. I finally got to a good balance between reading and writing.

This book contains multitudes. The specificity of some of your pop culture references really resonated with me. I’d like to ask about a few. First, why was Grover your favorite Sesame Street character?

I’ve always rooted for the underdog. He was not the famous or popular character on Sesame Street, so I really embraced that. But the best book in our house for a kid, and there weren’t many, was this book that somehow wound up in my meager library, The Monster at the End of This Book. It’s narrated by Grover and it’s a whodunit. It’s very meta in that Grover addresses the readers and acknowledges they’re reading. I couldn’t have put it into words at the time, but I was really blown away that he was breaking the fourth wall. It instilled in me a lifelong love of mystery and whodunits, but also this thing where the art is aware of itself. I’ve always found that compelling, and I’m almost certain it originated with reading that book.

At one point, you reference a favorite Bugs Bunny cartoon (“Baseball Bugs”). I share your preference for vintage Looney Tunes over Disney. Who is your favorite WB cartoon character?

Bugs Bunny. It went beyond him being a sharp, clever, funny character. There is a clear Jewish aspect to him. It was never stated, but I sensed he was out of the Jewish variety of humor. He was always a counterpuncher. He was always reacting to somebody messing with him, and I really admired that. He was put upon and then responded with his catchphrase, “Of course, you realize this means war.” Bugs had great confidence. He was always on a lower status than the people he reacted to, but he would stand up to anybody. Bill Murray, Chris Elliott, and [David] Letterman were always great at that. I’ve always admired those kinds of characters.

You write that one of the first laughs you remember getting was doing an Inspector Clouseau impression, but that before that you wanted to tell jokes on TV. Who were you watching growing up?

There were three shows that had comedians regularly: Merv Griffin, Mike Douglas, and Johnny Carson. I discovered David Brenner on The Mike Douglas Show. It was magical to me because it was so eerie that he was doing this observational humor, and it felt like he was spying on us. It made me laugh, but also it was so empowering that this man I always pictured as how I would look when I grew older, was behaving very creative. I loved George Carlin’s silly ideas about language and his observational stuff. Later on, I came across Garry Shandling. My brother had been bumped from a flight and got two free tickets but couldn’t use them, so for my bar mitzvah, my mother took me to Los Angeles, and we waited in line with my cousin Della to see Johnny Carson. Garry Shandling was his guest. I fell in love with him immediately. It was this interesting thing where a man was very neurotic and anxious, but also seemed to have that Bugs Bunny confidence. The other guest was Carrie Fisher, and he was flirting with Princess Leia. I eventually worked with Garry Shandling at the Comedy and Magic Club in Hermosa Beach; he couldn’t have been nicer. It was a really great meet-your-heroes moment.

You also write about ABC Afterschool Specials, which today would probably be targeted for being too woke.

They were very influential on me and had a great impact. They were very compassionate and empathetic. They were for the most part beautifully done. They were great at putting you in someone else’s shoes, usually an underdog or an oppressed person. There was one about a child with hearing-impaired parents and another about a boy who befriended a neighbor who was developmentally challenged. It was really important programming. I tuned in every week.

Your recent stand-up has evolved into these masterful long-form stories. Did that help you in writing the book, or was it the writing the book that shaped your stand-up?

The book has helped shape my stand-up and reminded me how important it is to be deliberate with words and phrasing. What I was told early by my editor was the process of building suspense. I realized that stand-up jokes depend on some level of “and then what happened,” so I realized I did have some experience with it, and it was just a matter of developing it. I wrote and rewrote the library book story so many times because it was important to maintain that what is going to happen to this kid; it was important to realize that the stakes in the moment were enormous and life and death.

Did The Great Depresh free you up in how much you chose to share in the book?

The Great Depresh was a gift to me on so many levels, and such a blessing. I didn’t mind that (prior to that special) a lot of my jokes were very low stakes and very silly and light, but it enabled me to show the other side to the audience that I had developed over the years. The audience has been generous with me in terms of allowing me to talk about things that in some cases were actually very heavy and disturbing. That was a very good transition that I understood I could be accepted on a different plane that I had been traveling on.

You’ve talked about your basketball days in your stand-up, and you write further about it in your book. You wrote that after setbacks: “I would first feel discouraged, hopeless, suicidal, then lick my wounds, and rededicate myself with more discipline and effort.” Did you adapt that work ethic toward your stand-up?

Since October 2017, I’ve had an uninterrupted recovery and I recorded the two specials and wrote this book. Before then, I would have six good months and then three months where my depression and career setbacks would undo me. The one thing I will say in my favor is I was resilient. I would always rededicate myself and work harder until I didn’t. Now I feel like the hard work is more in terms of trying to reach my potential than reach some goal of some sort of recognition or career milestone. I knew going into writing this book it would be an accomplishment to finish it and write it in a way I was pleased by. If it didn’t sell well or wasn’t embraced, I could live. I would have a couple of days of licking my wounds, but it wouldn’t be a long period of second-guessing myself.