On a warm July evening, Lee Stringer relaxes with a smoke outside lush Gramercy Park. In an hour, the first leg of an intense media campaign for his second memoir, Sleepaway School: A Boy's Life, will culminate with a James Lipton—like, Inside-the Actors' Studio "conversation" in front of a sizeable, eager audience at the posh National Arts Club. Leaning against the park's locked entrance, Stringer pauses to reflect on a life that has seen him rise from the depths of addiction and homelessness to the cusp of literary fame.

"Just after I published Grand Central Winter, my publisher called me and said the United Nations wanted me to come and speak," he says, a smile emerging. "I thought, isn't that just like life. One day you're smoking crack under Grand Central, the next you're addressing the U.N." Stringer snickers, and takes a drag on his cigarette. "What really is meaningful about that," he explains, "is that now people can look at a guy on the street and know that he matters. That person matters. He just hasn't been heard."

Once down and out, Lee Stringer has certainly been heard. Today, there are more than 65,000 copies of the hardcover edition of Grand Central Winter in print, a successful paperback edition from Pocket/Washington Square Press, and 12 foreign editions. Amid a parade of glowing reviews, Stringer has also earned the praise and friendship of fellow writers, including iconic author Kurt Vonnegut, who once hailed Stringer as the next Jack London.

If getting clean and writing his first book, Grand Central Winter, challenged Stringer, so too did Sleepaway School, a lyrical, elegantly written memoir of Stringer's turbulent upbringing in upstate New York. "There's no greater challenge in American letters than the second book," says Stringer's editor, Seven Stories publisher Dan Simon, who has been there for Stringer through both of his literary efforts. Stringer is quick to agree. "The first book was waiting to come out in a way," Stringer says. "The second book was definitely tough. Especially after having had some success. It was hard to get out of my own way, hard to let go of my intentions. I certainly didn't want to do anything I had done before."

Indeed, it has been a remarkable second act for Stringer, one that owes, in part, to circumstance and to the unpredictability of the New York Metropolitan Transit Authority. In the mid-1990s, homeless and addicted to crack, Stringer was both writing for and selling Street News, the now-defunct paper sold by the homeless mainly on New York's subways. One day, Stringer sold a paper to Simon. "Mind you, people at the time saw Street News mostly as a kind of informed samaritanism," recalls Stringer. "The idea was to get the buck in the person's hand. I assume Dan had set out to do that. He bought a copy, and tucked it under his arm. Then the train got stuck in the tunnel for about 25 minutes. So, after awhile, he pulls out the paper and reads it."

Simon says he found Stringer's writing in Street News "electric" and "bristling with ideas." Upon returning to the office, he quickly got in touch with Street News. He asked how he could help the paper, and then set up a meeting with Stringer, where he raised the idea of a book. For Stringer, who was still in the throes of addiction, signing up for the book was an easy choice. "Dan said, 'I don't want to rush you, but if you think you're ready, would you be interested in doing a book?' " Stringer recalls. "I thought, hmmm... book, advance, money, crack. Yes! I'll write a book!"

Not surprisingly, things didn't go smoothly at first. Stringer struggled to write the book while still using drugs. Eventually, he put himself into rehab. After getting clean, he scrapped a140-page draft he recalls as a "self-righteous" first effort, most of which was written under the influence, and with a generous give-and-take between author and editor, ultimately rewarded Simon's trust. Grand Central Winter was universally praised for its sharp eye and humane voice, revealing Stringer to be a gifted writer.

Grand Central Winter remains a major achievement for Stringer. Sleepaway School, however, Simon muses, may be an even grander achievement. With the publication of Sleepaway School, he notes, Stringer has proven to critics that he did not merely catch literary lightning in bottle with his first book, but has shown himself to be a singular voice. "In both Sleepaway School and Grand Central Winter Lee gives himself a past, and then frees himself from it," Simon says. "They're both lasting works."

Sitting on the dais at the National Arts Club, Stringer delights the audience with his charm and insight. He is relaxed and gracious. He appears perfectly at home amid the Club's old wood and 19th-century oils, although Stringer himself concedes that he never could have imagined, addicted and homeless, that he'd one day be an honored guest addressing at a members only arts club in Manhattan's tony Gramercy Park.

"No, I never imagined this. At one time I thought I'm either going out at the end of crack pipe, or, I might get off crack, but even then I couldn't say what I would do with my life. With Grand Central Winter I just hoped that it would sell a few thousand copies so maybe I'd get a chance to write another book." When asked about the strength it took to reclaim his life and find his literary talent, Stringer hedges. "I don't think it's about strength, really." he says. "It's about honesty more than strength. If you're ever in doubt, honesty and the declarative sentence will get you through."