I will never forget how I found Gary Gulman. It was seven or eight years ago, maybe more, and I was in the car listening to one of those comedy radio stations on XM Radio — you know, this was before comedy died. I pulled into the garage and was about to turn off the engine and go inside when the the host or DJ (or whatever a comedy radio station narrator is called) said that he had an unusually long bit to play.

“We don’t usually play routines this long,” he said. “But you have to hear the whole thing because it’s so brilliant.”

And then, I heard this:

“We’re in a golden age of cookies,” Gary Gulman said. “A golden age, my friends.”

Cookies. The whole routine was on cookies. Gulman went on for THIRTEEN MINUTES on cookies. It was roughly the Gettysburg Address but six times longer and on cookies. It was unlike anything I’d ever heard before.

Yes, in a general sense, Gary was doing stuff that everyone now calls Seinfeldian. Jerry Seinfeld had all but trademarked beautifully crafted comedy about every day things like breakfast cereal and halloween masks and how excited dogs get every time they see you.

But Gary Gulman took this to a whole other place. He asked Pepperidge Farm if they needed to use quite that much paper in their cookie packaging. He marveled at how bold it was for Fig Newtons to build an entire business model around the fig. He revealed that the full name of Hydrox cookies is “Hydrox by mistake,” because that is the only way anybody ever buys them over Oreos — “Oh, sorry,” his mother would say, “I got Hydrox by mistake.” He showed genuine admiration for the gimmick of putting fortunes inside flavorless fortune cookies (“Yeah, we’re giving you a lousy cookie, but inside that lousy cookie? Hope.”)

He said that the worst cookie is the sugar cookie.

“All cookies have sugar,” he finished. “A cookie without sugar is a cracker.”

What separated him from Seinfeld or any other comedian I’d ever heard was the relentlessness. He kept going and going and going and going; it was as much an athletic feat as it was a comedy routine. The laughter came from two places — the hilarious observations, yes, but also the audacity it takes to ramble about cookies for that long and to somehow keep finding new ground. Keebler elves! Oreo double stuff (“Same price for double the stuff!). Nutter Butter (“It’s cute how your name rhymes but stay in your place). The farmers who till the Milano fields for Pepperidge Farms.

And he kept going still. it was like watching someone make 500 straight free throws.

Years later, after we became friends, Gary told me that he actually was and remains an incredible free-throw shooter. He can still go out there and shoot 90% from the line like he did in high school.

It isn’t a coincidence.

“Show me someone’s free-throw percentage,” he says, “and I’ll tell you the exact time his single mother came home from work.”

* * *

The Great Depresh debuts tonight (Oct. 5, 10 p.m. Eastern, on HBO) and it will be available for streaming beginning Oct. 6, and it is unlike any comedy special ever made. One of the most celebrated bits of pop-philosophy is that there is a thin line between comedy and tragedy. In The Great Depresh, there is no line at all.

The special features Gary, his mother, his wife, and his therapist. That itself sounds like a joke, but it’s the opposite of one. Gary is there to tell jokes about the worst time of his life, a time when he was so depressed he could not get out of bed, a time when suicidal thoughts were constant, a time when he had to quit the thing he loved most, stand-up comedy, because he lacked the strength and energy and will to stand.

His mother, wife, and therapist — three blatant tropes for in the world of stand-up comedy— are there to tell the same story without jokes. They are the ones who remember it best. They are the people who worried he would never recover.

They helped him survive.

All of it is so raw, so powerful, so agonizing and … so funny. Gary often says on his Twitter account that he is at the height of his powers, and you sense that he’s hoping to make you smile at his flagrant braggadocio. But only an artist at the height of his powers could pull off something like The Great Depresh. He gets laughs about the dozens of drugs he’s taken to ease his depressions. He gets laughs about the pain of being constantly misunderstood as a child. He gets laughs, impossibly, about the electroconvulsive therapy he went through. Nothing is off-limits. Nothing is beyond his comedy reach.

The old line that making someone laugh is harder than makings someone cry is no doubt true.

But there are times during The Great Depresh when you will not be sure which one you are actually doing.

When Gulman was a younger comedian, he came out with a rat-tat-tat of jokes and observations that would leave people in the audience struggling to breathe through the laughter. As he grew older, he would take you on wild rides like his bout over grocery cart legal doctrine with a woman at Trader Joe’s or, most famously, his legendary breakdown of a documentary about the abbreviation of the states.*

*This is not a real documentary. I only say this because people have constantly asked Gary where they can watch it.

All of this brilliance came from Gulman’s relentless work ethic. He became a great free throw shooter by spending countless hours alone shooting free throws. He became a great comedian by spending countless hours alone writing jokes (his now famous Twitter #GulManTip thread offers advice to young comedians, and most of that advice is about writing and writing and writing some more).

Gulman was, in his own way, the purest of comedians.

But The Great Depresh required something else of him — a brutal kind of honesty that required him to go back again and again to the most painful moments of his illness, to try and find hope where he had only felt hopelessness. He absolutely was not sure he could do it. He went repeatedly to his wife, Sade, and asked her to describe for him the lowest points because he had blotted them from his mind. He took the stage in small comedy clubs repeatedly armed only with material he wasn’t sure would make anyone laugh and Samuel Beckett’s challenge to fail better.

“It sounds like ‘feel better,’” he says. “I don't think that’s a coincidence.”

The end result is a special that feels new and haunting and hilarious and painful and, ultimately, triumphant. It’s a hard special to sum up because you will inevitably make it sound sad when it’s not sad or hysterically funny when it’s so much more than that.

Gary has always railed against what he calls “clapter,” which is when an audience responds to a joke with more applause than laughs. He is no fan of clapter; a joke is supposed to make someone laugh. “If your joke only elicits applause,” he wrote in one of his #GulManTips, “it’s not a joke, it’s a slogan.”

No, he doesn’t like clapter … but it seems to me that in The Great Depresh he stops for a moment and embraces it, embraces the mixture of laughs and tears and applause and love that surrounds him. The fight is not over for him, not by a long shot. He had to give up comedy for more than a year, his wife worried that he would never do comedy again, and he worries about backsliding. Every single day he goes through various steps to keep his illness at bay.

The greatest hope is that the love that comes from this special will help sustain him in his darkest moments.

But I will tell you this: I saw Gary a couple of weeks ago in Atlanta. He has a whole new show that he’s about to take on tour, and it’s hilarious, ridiculous, rat-tat-tat, it’s a whole set of wacky observations and deep dives into things like precipitation and great old baseball players. This is the old Gary Gulman, the comedian I first heard in the car all those years ago.

And here’s how I know: At one point, he told a joke, and the crowd applauded ferociously, and he shook his head.

“OK,” he said. “that didn’t work. Back to the drawing board.”

For more with Gary Gulman, please check out this week’s PosCast, available on Apple Podcasts and Spotify and Stitcher and wherever you get your podcasts.