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There’s a deep divide in this country that may never fully heal. We can’t find consensus on any of the biggest issues of our time, from climate disasters and the collapsing democracy to the culture wars and the ongoing pandemic.

One thing we can all agree on, however: We’re living through a disturbing, disastrous era of history.

Given that reality, Eddie Pepitone’s friends in the world of comedy have one question for him: “Are you happy now, Pepitone?”

The comedian’s act, fine-tuned over decades of obscurity, is not for the faint of heart. Sprinkling tentative stabs at enlightenment into his default mode — volcanic rage — his comedy revolves around the indignities, great and small, of the modern world. He has several shows around New England early this month, including headline appearances to open the Rogue Island Comedy Festival in Portsmouth, R.I., on Oct. 7, followed by shows in Provincetown Oct. 8 and Worcester Oct. 9.

While it’s amusing to equate this hefty, unkempt, foul-mouthed product of Staten Island with the delicate beauty of flowers, he is in fact a late bloomer. Pepitone didn’t cut his first album until 10 years ago, when he was already in his 50s.


But his raw social commentary has made him a favorite of his fellow comedians. After years of dues-paying, touring with the Chicago City Limits improv troupe and appearing with the Upright Citizens Brigade in New York and L.A., he has broadened his profile with appearances on late-night television, on sitcoms, and as a voice actor in animated series. Last year his second comedy special, “For the Masses,” was named best of the year by the New York Times.

“All it took for you to get big was the complete breakdown of society,” Pepitone says, recalling what one of his friends told him recently. He cackles.


“As soon as there’s a full-blown apocalypse, you’re gonna be the best.”

Some of his bits imagine absurd scenarios, improv-style — a lounge singer who sings about our weird fixation on true-crime TV shows, say, or a “Price Is Right” segment that asks contestants to guess the cost of the Iraq War. On social media, he has perfected the art of contrasting horrible news with our relentless marketing machinery: “California is running out of water! BUT Chipotle is not running out of deals.”

He has little hope for the human race in large part because, for most of his 62 years, he had little hope for himself. In “The Bitter Buddha,” a 2013 documentary directed by Pepitone’s friend Steven Feinartz, fellow comedians Patton Oswalt and Marc Maron, to name a couple, helped explain Pepitone’s perverse appeal to a wider audience.

By then he was sober after years of reckless behavior. One colleague called him “the Charles Bukowski of comedy,” if you replaced the booze with Nutter Butters.

The film opened with a title card that spelled out his self-deprecating streak: “The only things stopping me today are: genetics, lack of will, income, brain chemistry, and external events.”

“I think everyone has to go through this, at whatever age,” Pepitone says, speaking on the phone after a brief struggle with his iPhone AirPods. (Lately he’s taken up digital drawing, posting his work on Instagram. A neurotic thicket of frantic, loopy lines, the drawings suggest Jackson Pollock grappling with tangled headphones.)


“There’s such incredible doubt on your journey to being decent at something. The paradox is you have to be so lost at some point to find what you want.

“It’s like ‘Dante’s Inferno,’ ” he continues. “You have to be completely lost in one of the nine circles of hell to get the [heck] out of there.”

Pepitone’s father, who is 88, still lives on Staten Island, supported by the pension from his career as a public school history teacher. Though his father’s own anger issues often come up in Pepitone’s act, he has childhood memories of them enjoying Walter Matthau movies and Jackie Gleason in “The Honeymooners” together.

If it weren’t for comedy, Pepitone says, he might be eligible by now for his own pension from a civil service job.

“They actually call it the ‘borough of the white socks,’ ” he says of his old neighborhood, home to so many cops and postmen.

He’s finally come to terms with himself, he says, and he attributes his late-career success to that fact.

“That’s the biggest key,” he says. “Just not being afraid of being vulnerable and letting people know who you are, which is a completely flawed individual.” We’re all flawed in our own way, he adds with a laugh: “Oh God, it’s a bloodbath of flaws.”

In earlier years, he was often paralyzed by nerves before a performance. “I’ll never forget, one time I was in a bathroom stall throwing up, asking myself, ‘Why am I doing this?’ ” When aspiring comedians approach him for advice, he tells them, “You have to have a very unhealthy need to do this.”


After he got vaccinated earlier this year, Pepitone was thrilled to get back out in front of live audiences. His attempts at doing comedy on Zoom were “hilariously bad,” he says.

One recent night at the Comedy Store on Sunset Boulevard, where he drops in to work out new material, he told a friend how grateful he was to be back onstage. “I said, ‘You know what? This is gonna sound dramatic, but I’d rather die doing what I love than sitting at home.’ ”

Not for the first time, he couldn’t believe such a thing came out of his mouth.


At the Shaskeen, Manchester, N.H., Oct. 6.; Rogue Island Comedy Festival, Portsmouth, R.I., Oct. 7; Red Room, Provincetown, Oct. 8; Ralph’s Rock Diner, Worcester, Oct. 9. Ticket information at www.eddiepepitone.com.

James Sullivan can be reached at jamesgsullivan@gmail.com. Follow him on Twitter @sullivanjames.