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A couple of years ago, Jeff Simmermon’s grocery bags tore open on the subway.

It wasn’t the sort of event that would rate as seismic in anybody’s life. It certainly didn’t for the 40-year-old Simmermon, who in the last eight years has had his fair share of life-shaking events: He lost his left testicle to cancer, launched a performing career and appeared on This American Life, got married, quit a six-figure white-collar job to pursue comedy full-time, and got divorced. But when Simmermon turned that anecdote about the grocery bags—and the weirdly civil shouting match that followed—into a five-minute tale at a Moth “GrandSlam” storytelling competition in Brooklyn last year, he imbued it with all the humor, surprise, and observation due a matter of life and death. A YouTube clip of the story earned more than 100,000 views.

It also helped persuade Comedy Dynamics—a “comedy production-and-distribution” outfit that’s put out specials and albums by blue-chip comics like Louis CK, Aziz Ansari, and Kevin Hart—to invest in Simmermon. Though he moved from D.C. to New York almost a decade ago, he has chosen the Black Cat as the venue for his debut album. On Dec. 15, he’ll perform two hour-long sets at the club’s 200-capacity Backstage room, which will be edited for release in the spring.

Disclosure: I’ve been friendly with Simmermon for 30 years, since we were in the same summer kiddie-theater production of You’re a Good Man, Charlie Brown in 1986. As adults, our paths have crossed infrequently, but I have been pleased to see a dude I always liked develop into an artist I admire.

The Black Cat, where he has headlined story shows on several occasions in the last five years, has always been an aspirational lodestar for him. As a high schooler in Norfolk, Virginia, he fell hard for Bad Brains and Fugazi and the Dischord Records lineup: “That was just rock and roll,” he says. While in college in Harrisonburg, and in the half-decade he lived in Richmond afterwards, he made frequent road trips to the club. After a 2003 walkabout in Australia that provided the grist for one of his best stories, a tale about his brief career as an assistant to a kangaroo hunter, he moved to D.C in 2004. It was the era of blogs, and Simmermon was producing an average of three essays per week for his: And I Am Not Lying.

In the years since, he’s come to appreciate the place as much as a performer as he did as a fan. After relocating to Brooklyn in 2008, he discovered that mining his experiences for laughter and applause from the stage was more rewarding than cranking out blog posts. And I Am Not Lying was reborn as a semi-regular live storytelling-and-burlesque series with collaborators Brad Lawrence and Cyndi Freeman. When Simmermon brought the lineup down for its Black Cat debut in 2011, proprietor Dante Ferrando worried that the “burlesque” part might run afoul of Alcoholic Beverage Regulation Administration rules.

“Instead of just saying no, he spent an hour on the phone with me while we figured out how much of Cyndi’s breast would have to stay covered by a very particular kind of tassel in order to meet the legal obligation of his liquor license,” Simmermon recalls. “That’s huge to me.”

Though he’ll perform material that’s been thoroughly road-tested, he expects that recording in the District will give him a fresher, friendlier room. “Per capita, there are way more people more hungry for new stuff and willing to gamble $15 on a person that hasn’t appeared on television,” than in New York, he says. Because D.C. isn’t a comedy mecca, he doesn’t have to contend with distracted scenesters who may only have turned up because they heard a rumor that Amy Schumer or Chris Rock might drop in. That’s more of a concern since he’s decided to realign his focus from the nurturing, sweater-vested world of storytelling to the more cutthroat realm of stand-up. 

“Storytelling people are a lot nicer than comedy club people,” says Jennifer Hixson, senior producer of The Moth and co-host of its radio show and podcast, The Moth Radio Hour. She’s coached Simmermon for as long as he’s been performing. “With comedy, people have their arms folded. ‘Okay, make me laugh.’”

She’s talking about the audiences, but Jeff extends the observation to performers. The storytelling community is friendly and nurturing because, Mike Daisey or Henry Rollins aside, there’s no quitting your day job when your art is the art of the monologue.

“Once you remove any hope of ever succeeding in any tangible way or ever making money, everyone gets incredibly nice,” Simmermon says.

Though after college he performed in a band whose lineup included live chickens—the subject of another oft-told story—he was set on his current path when a pal from his years in Richmond who’d moved to New York before he did brought him to an open-mic Moth “StorySLAM” in 2008. “It was like watching the sword come out of the stone,” he remembers. 

He began performing as often as he could, and he had success relatively early. He advanced to The Moth’s championship-round “GrandSlam” stage in 2009, where he lost the story contest. But his tale—about defending his younger sister from an abusive high school boyfriend via unconventional means—caught the ear of Seth Lind, who at the time was hosting a different weekly live storytelling series called Told. 

Lind had the same day job then that he does now: director of operations for This American Life, the popular (mostly) nonfiction radio magazine that claims an audience of 4.6 million listeners per week via radio and podcast. A recording of Simmermon’s story was featured on the 2009 episode “Pro Se.” Host Ira Glass took the unusual step of interviewing him about the story in the studio afterward.

Lind remembers that Simmermon was an imposing figure on stage, not least for his appearance: 6’2” and north of 200 lbs., with a large, bald, egg-shaped head and a bushy beard. He dressed memorably, too.

“Jeff is someone who takes style seriously in a way that most performers don’t,” Lind says, noting that he’s typically seen him perform in either a three-piece suit or a flamboyant cowboy shirt.

“Powerful and intense,” is how he characterizes Simmermon’s stage demeanor, observing that a lot of stage storytellers either favor or default to a quieter approach, not just in volume but in tone. If you’ve ever attended a SpeakeasyDC or Story District event, or one of The Moth’s DC story slams, you’ll know what he means. Lots of beards. Lots of slouching.

But even before he decided to reposition himself as a comic, Simmermon’s performing demeanor was calibrated to demand attention. “He’ll kind of go off on a tear,” Lind says. “He’ll amp up his Southern accent a little bit, particularly if the story takes place in the south. I thought that was smart, particularly in NYC, because it feels like that gives you some legitimacy if you’re talking about the south. He’ll be amping up the accent a little bit as the story crescendos. He gets into a rhythm and is delivering the words in a musical way as the story climaxes. It’s very satisfying.”

Hixson, who has coached hundreds of storytellers in her 17 years with The Moth, says that Simmermon’s performing persona, while practiced, is still recognizable as the person he is offstage. “You see some [storytellers] where you just know they would never say it that way ordinarily,” she says. Hixson typically listens to Moth GrandSLAM performers tell their stories by phone and offers coaching. She recalls that before his first GrandSLAM Simmermon kept calling her back to audition refinements. “He’s a very hard worker,” she says. “He’ll debate a word choice. That’s fun for me.”

Details matter.

“I have this huge chip on my shoulder about being perceived as comedy,” Simmermon says. “I hope this album will establish me as a comic who happens to tell stories, rather than a storyteller who happens to be funny. There’re a lot of storytellers who hide behind the lower standards of entertainment that the storytelling scene has. But no one is going to hire a babysitter because I had some exciting revelations in my third act,” he says. 

It’s a line I know he’s workshopped because he’s said it to me before. It’s not extempore. But it’s exactly right. And now it’s on record.

Jeff Simmermon performs with Anthony Devito and Gastor Almonte at the Black Cat on Thurs., Dec. 15. 1811 14th St. NW. $15.