It was five minutes before curtain time, and Matt Graham—the comedian, Scrabble savant, college basketball might-have-been, and self-described “classic New York eccentric”—was in his dressing room, attempting to memorize the lines to his one-man show. He was wearing blue canvas sneakers, boxy glasses, and a T-shirt that read “Real Men Love Cats.” There was a knock at the door, and Ira Freehof, a friend of Graham’s from the professional Scrabble circuit, burst in to wish him luck.

“You didn’t return my texts, Ira,” Graham said. “I told you I needed money, right? Because Ruth was sick? Well, Ruth died last week.”

“Wow,” Freehof said. “She did?”

“He.”

“He did? Wow.” Ruth was the love of Graham’s life, and was also a cat.

“You should go now,” Graham said.

“Me?” Freehof said.

“You,” Graham said. Freehof left.

“He’s one of my closest friends,” Graham told me.

On the other side of the door, waiting for the show to begin, were about two dozen people who had successfully located the Kimball Studio, a tenth-floor loft space near Union Square. Inside the dressing room, Graham, who is forty-six but has a restless, childlike demeanor, went back to poring over the script he’d written. He was interrupted again, this time by himself. “Have I told you about my first time on Conan?” he asked me. He launched into that story, which reminded him of another story. “See, this is why I never quite made it in show business,” he said. “I should memorize my lines, but I’m more interested in just talking to you. I can talk about myself at length, and intelligently, but I’ve got no goddamn work ethic.”

Maybe so, but Graham did come close to making it in show business. After dropping out of high school in Indiana, he moved to Boston in 1985 and began performing his brainy, off-kilter jokes at open mics. Within a year or two, he had earned the admiration of some of the best comics in town, including David Cross, Louis CK, Bill Hicks, and Marc Maron. Janeane Garofalo, then a good friend, told Graham, “You’re the one guy in this town who everyone agrees is going to be famous.”

Graham moved to New York in 1994, and performed several times on Conan O’Brien’s late-night show. He favored absurdist one-liners in the Steven Wright tradition. (Carrying a bag of groceries to his walk-up apartment, he deadpanned, “I stumbled, all the groceries rolled down the stairs—except for a can of salmon, which fell up the stairs … Couple nights later I was driving the wrong way down a one-way street. Cop pulled me over. I told him I was spawning.”) In 1998, when Colin Quinn replaced Norm MacDonald as the anchor of Weekend Update on “Saturday Night Live,” Quinn hired Graham as one of his two staff writers. It was Graham’s first full-time job, and it could have been his big break; but he was drinking heavily at the time, and even Graham admits he was difficult to work with. Colin Quinn told me, “Matt Graham was like a high school Indiana point guard that drives you nuts, because he’s got all that talent, but he almost deliberately misses easy jumpers because he’s bored by the game.” Within four months, he was fired.

Stung, Graham withdrew from show business. His alcoholism and depression worsened. He also developed an addiction to GHB, a powerful sedative. He moved from the Upper East Side to a converted utility closet in Harlem, where the rent was, naturally, less expensive. To pay it, Graham took the train to Washington Square Park and challenged onlookers to five-dollar games of speed Scrabble. He was uncommonly good, and he soon grew obsessed with the game; he entered several World Championships, finishing as high as second place. “In Scrabble I pull randomness and create order,” he told me, “and in comedy I am making observations about the world and translating them to an audience. Scrabble is a math game, mostly, and my jokes are very mathematical.”

Graham got sober, and reined in his Scrabble habit. He found other ways to pay his bills—tutoring, writing for cable TV game shows—but he still felt directionless. In 2004, he set a new goal for himself: he wanted to play N.C.A.A. basketball, at the age of thirty-nine. In order to join a college sports team, he would first have to enroll in college. He passed the G.E.D. test and took the S.A.T. (after studying Scrabble vocabulary, he says, his verbal score was perfect). Then he availed himself of a Pell grant and enrolled at York College, a CUNY branch in Jamaica, Queens. His classes bored him, but he thrived in basketball tryouts, despite his osteoarthritis. “I could shoot threes; I could move with the ball; and I always made sure, when we’re running drills, that I was never the last guy to finish.” In the end, though, Graham did not make the roster. Instead, he became the team’s announcer during home games, which was the closest he had come to performing publicly in years. During that time, Graham says, “If someone asked me, ‘What do you do?’, I might say, ‘I play a little Scrabble,’ or ‘I’m going to college.’ Never ‘I’m a comic.’ I wouldn’t even think it.”

That changed suddenly last fall, when Graham decided he would try to be a comic again. He now lives by himself in Richmond Hill, in a studio apartment he has filled with fifteen hundred books, seven hundred DVDs, and three hundred vintage board games—and he spends much of his time there writing new jokes. He has performed a few of these, along with the old classics, at small comedy venues in Manhattan. And he is still revising his one-man show, which is smart and surprisingly poignant, and which he hopes to bring to the New York Fringe Festival. “I’m good with words,” Graham says, “and I think I have something to say. It doesn’t always work, because I have an enormous ego, but sometimes, when I get out of the way, I can really touch people.”

Photograph by Ann Sanfedele.