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A Deeply Strange New Year’s Eve With Dave Chappelle

As relayed by Ben Jealous, outgoing head of the NAACP

Brank X PIctures/Humphrey Spender/Fox Photos

From our occasional series of vignettes about unlikely interpersonal interactions 

It’s New Year’s Eve 1999, and as Dave Chappelle looks over his acres upon acres of property outside of Yellow Springs, Ohio, he decides he needs a gun.

“What do you see out there?” the actor and comic asks his god-brother, Ben Jealous, the future NAACP president.

“Cornfields,” Jealous replies.

“How many do you think are owned by brothers?” Chappelle asks. “Tonight is Y2K. It is the ending of a millennium. Everything could be fine tomorrow. Or it could be the race war that ends the world.”

They promptly head to a Kmart outside of town, along with Chappelle’s brother, who is a convert to Islam dressed in traditional Muslim clothing, and the comedian’s best friend from childhood, a religious Rastafarian with vine-like dreadlocks. An older woman, a greeter, stops them at the door: “Gentlemen, how can I help you?”

“Ma’am, where’s the gun section?” Chappelle says, granite-faced.

She noticeably tenses up and moves cautiously over to the intercom. “Help in the gun section,” she calls. “Help in the gun section.”

Chappelle and the rest head to the back of the store to find a young man Jealous still calls Howdy Doody behind the counter. He’s freckly, redheaded, 18 and a day.

“How can I help you?” Howdy Doody asks, taking a nervous gulp.

“I want the biggest, blackest shotgun that you have, son,” Chappelle replies.

Howdy Doody hands him a shotgun off the rack. Chappelle, who knows nothing about guns, holds it up in the air and, for practice, yells, “Get off my porch!”

The comedian turns back to the clerk. “Not big enough,” Chappelle says, sucking his teeth in faux frustration. This goes on, gun after gun, until Chappelle finally decides on a double-barrel 12 gauge Mossberg.

None of the four wants to haul this gun, even wrapped in cardboard, through the store. “Gentlemen,” Howdy Doody says. “State law. I’m going to have to carry the gun to the vehicle.”

So the men fall in single file behind the freckle-faced ginger, who holds the gun in front of him like a processional flag. This, as all the other people in the store look on, open-mouthed.

Back at the house, Jealous is the only one who knows how to shoot a gun. He loads the fine-grain birdshot into the magazine and starts his lessons. Chappelle grasps the stock, rests the butt on his shoulder, and aims the muzzle at a plastic water jug they’ve placed on a fence post. He won’t need the gun tonight or any other night, but in the eerie Ohio silence, he pulls the trigger.

Ross Kenneth Urken is a writer and editor based in Manhattan. He has published in The Wall Street Journal, The New York Times, The Paris Review, New York, Forbes, and The Atlantic. Find more of his work here and here.