He kept hearing he'd have to hit rock bottom before he could bounce back, but every time he thought he was there, the ground would give, and he'd sink even lower. There was the time his best friends had a security guard break down his apartment door because they feared he'd died of an overdose. There was that coke-fueled night in some singer's apartment with three strippers, one of whom attacked him with scissors before the other two began pounding her face. There was the warning he received to quit speaking to that mobster's girlfriend, during one of those misadventures that helped inspire the movie "Rounders." There was the time he went to House of Blues planning to hang out with Jakob Dylan and instead spent a night at Cook County Jail. Most of all there was the disappointment, always the disappointment, that sunk into him like talons and dug deeper with each passing year. This was all before Italy, before Heather, before Rain, before the fight for grace had become worth it. When they called Michael McDermott the new Bruce Springsteen or Bob Dylan, he believed it. He took to heart The Washington Post's declaration, upon his first album's 1991 release, that he "may well become one of his generation's greatest talents." He saw himself in Rolling Stone, on MTV, in The New York Times. Stephen King quoted his lyrics in the novel "Insomnia," phoned him at his family's Orland Park home, took him to a Cubs game and wrote in the liner notes of his third album: "Not since I first heard Bruce Springsteen singing 'Rosalita' had I heard someone who excited me so much as a listener, who turned my dials so high, who just made me feel so (expletive) happy to have ears." Yet for all that, McDermott didn't happen. "By the time I was 24, I was over," the singer-songwriter says over a half-eaten plate of chicken tacos in his Edgewater neighborhood. "Really, I was kind of over." But far from done. He kept writing, recording, performing and spiraling, and now, at 42, married with an 11-month-old daughter, McDermott is ready to revisit the launch pad that turned out to be more of a diving board: On Saturday night he and his band will mark the 20th anniversary of the release of his debut album, "620 W. Surf," by performing it and its follow-up, "Gethsemane," at Lincoln Hall on the North Side. "620 W. Surf," with McDermott's gruff voice delivering wild flights of imagery rooted in classic folk-rock arrangements a la early Springsteen, was supposed to propel the then-22-year-old into orbit, but stalled somewhere closer to the ground. "It became this haunting thing," he says. "I stopped looking at it and stopped playing songs from it. As much of a blessing as it was, it became an albatross: Why didn't it do better?" Days before the concert, McDermott still hasn't relearned the songs or practiced them with his band. "It will be like going back and reading your old journals," he says. "That guy (on the album) was very different and hadn't had a drink and done drugs and gone to jail and had his heart broken." That guy is Michael Murphy, the youngest of four kids whose middle name, McDermott, became his stage last name so he wouldn't be confused with the other Michael Murphys out there. His dark hair is still longish, though not the lush mullet of his earlier years, and his brown eyes are on full alert, his thin mustache and goatee suggesting a troubadour musketeer. Amiable and eager to connect, he dredges up painful memories with the matter-of-factness of someone who no longer feels the need to plead his case. He was 19 years old and had considered becoming a priest when local producer Jim Tullio saw him at the long-gone Orphans club and was wowed by his writing. Kellman-Tullio Entertainment, co-run with Jack Kellman, offered him a management contract, and, Tullio says, he and McDermott recorded 22 demos in one day. "He was at my house all the time," Tullio says. "He was like a son to me. He came to me one day and said, 'Can we start shopping this?'" McDermott hadn't yet signed his contract with Kellman-Tullio — his parents' lawyers had been looking at it for months — and Tullio wanted the deal sealed before proceeding. But McDermott was antsy, so Tullio relented, and he and Kellman arranged for the singer to perform at Metro for Brian Koppelman, a young New York-based talent scout who had signed Tracy Chapman and at the time was working for Irving Azoff's Giant Records. "I was just three years older, but I couldn't believe a kid wrote those lyrics," Koppelman recalls, quoting the McDermott song "No. 49" off of "620 W. Surf": Lifelessness cries from the fountain of youth/ Lawyers debate the meaning of truth/ In the judge's chamber he downs his gin and vermouth/ And he cries when he sees his reflection. The next day, McDermott, guitar in hand and Tullio in tow, visited Koppelman in his hotel room and played for an hour and a half, "after which I knew that I wanted to work with him," Koppelman says, "because the songs were great, and he meant it so damn much." Tullio wound up driving McDermott to the airport so the singer could pay a follow-up visit to Koppelman in New York. "The last thing I remember saying to him is 'Don't tell him you're not signed to us (yet), because it really makes us look like we're not professional,'" Tullio says. "I think the very first thing Brian Koppelman asked him was, 'Are you signed with those guys?' and he says, 'No.'" McDermott acknowledges that Tullio "ultimately was responsible for getting me signed, really, and then, I did the classic (jerk) move. It was Darwinian, kind of. I knew I was going out in the animal kingdom and just wanted to go out with the strongest tribe. (Koppelman) is still one of my best friends in the whole world, so I stand by that decision. I guess it was a bit scummy." "620 W. Surf," named after McDermott's Lakeview address and produced by Don Gehman (John Mellencamp) with Koppelman, spawned the single/video "A Wall I Must Climb," which was put into MTV rotation.

"I was in Rolling Stone, and every newspaper was writing that I was the next big thing, really," McDermott says. "And that was great. I was a kid from Orland Park. I'd already exceeded my expectations. My dreams had already come true, and it's a weird thing when that happens at 22, because where do you go from there?" In McDermott's case he went into a world of strip joints, backstage parties and people trying to ingratiate themselves. "I'm touring, and every night there's Jack Daniels in your dressing room and all that, girls," he says. "Coke just always appears when you least need it." "He wasn't prepared for that stuff," says his brother Martin Murphy, an Orland Park insurance agent. "Of course, you're like a kid in the candy store when you get all those different things." "He was sort of living a star's life, and he wasn't a star," Tullio says. When Koppelman and David Levien wrote the screenplay for the 1998 drama "Rounders," they not only drew on their experiences with McDermott at underground poker games, but they named Matt Damon's protagonist Mike McDermott and gave the singer's actual last name to Edward Norton's more troubled character, Lester "Worm" Murphy. Says Levien: "He's more like the Worm character." The singer agrees. "I was getting myself into so much trouble that when (the character) Michael McDermott says to Worm, 'Man, it seems like you want to lose,' I mean, that was the same conversation those guys were having with me all the time." It wasn't a fun conversation. "The worst it got was New Year's Eve, around '93 or '94," Koppelman says, noting that he and Levien flew to Chicago after repeatedly failing to reach him on the phone. "We thought maybe he was dead in his room because he'd left some long, rambling answering-machine message the night before, and we had them —" "The security guys at his building broke into his apartment," Levien interjects. "And then we found him," Koppelman continues, "and there was an eight ball of coke in his fridge and open bottles of booze everywhere. We dragged him and got him to the airport and brought him back to New York to dry out. And dragged him to AA meetings. And that repeated itself a number of times." McDermott says "620 W. Surf" wound up selling about 30,000 copies, below expectations at the time. "Gethsemane," the more insistently rocking 1993 follow-up, didn't have the MTV support and fared worse, and after "Michael McDermott," his 1996 album for the soon-to-implode EMI, he found himself without a major label. "I took whatever money I had left, and then I made my own record here in town," McDermott says of his fourth album, "Bourbon Blue" (1999), "but I was, like, freebasing during vocal tracking." His albums still had their highlights, such as 2000's "Unemployed," with its powerhouse chorus: Hallelujah, I'm overjoyed/ I'm drunk again and I'm unemployed/ The things I've wanted I've just destroyed/ Drunk again and I'm unemployed. But his audience never grew. "Maybe it turned out that the world wasn't really looking for that," Koppelman says of literarily inclined singer-songwriters. "Because Conor Oberst (of Bright Eyes) never became that (star) either, and Craig Finn (of the Hold Steady) isn't even that. But I do think part of it is, if Michael owns any of the blame for that, it's because in the wake of '620 W. Surf,' he got lost." On Nov. 24, 2002, McDermott got frisked on the way in to see the Jakob Dylan-fronted Wallflowers at House of Blues and wound up in Cook County Jail for possession of a controlled-substance (cocaine). The arrest, under the name Michael M. Murphy, never made the news. Although his lawyer eventually got the charges dropped, McDermott says his overnight stay and the prospect of three to six years in prison put a scare into him. "You'd think that would be the end of it," he says. "It wasn't." The descent continued, another low point being a weekend spent at the Chelsea Hotel in Manhattan; he doesn't go into details, just says with a wince that it was "ugly, debasing, defiling stuff." Throughout the '90s and 2000s, Koppelman and Levien staged more than one intervention, but McDermott says rehab never worked for him. Leaning on his strong Christian faith didn't do the job either, though he says therapy was helpful. The plot twist finally came about four years ago, when he was in Bergamo, Italy, to open for another performer and spotted a man in front of the theater writing on a poster board: "Your silence I will always admire for its being," lyrics from a "620 W. Surf" song. When McDermott approached him, the man burst into tears and asked him, "What took you so long?" Turns out, Michael McDermott was big in Italy. Promoters asked him to tour the country, and he went back, without and with his band. Next month he'll return so Italian documentarians can film him performing throughout Italy. "I was so empty, and going over to a place that's so full up with life and love and family and food and music really changed me," he says. "Had I not had that tour, I would have never married, because I didn't know anything about love." Heather Horton, who's got a bright smile and warm energy, joined McDermott's band as a singer and fiddle player about six years ago, but at first she didn't see him much offstage "because he was really wild, and I wasn't wild, she said." Eventually, though, she discovered "a sweet and kind person" beneath the facade. When she moved to Nashville, she recalls, "he said, 'If I die, would you cover a song of mine? Would you do a song in my honor for me?' I kind of rolled my eyes, like 'you poor thing.'" But once she was gone, she heard tales of his behavior and noticed how "foggy" he was when she returned to perform. After shows she would take him back to the apartment where she was staying, "and we'd literally not tell anybody where we were, and we would sit in that apartment for two or three days until I had to go back to Nashville." She knew he wasn't ready to commit to one person, or to complete sobriety, but she made a decision: "I thought, this is my perfect mate, and he's not going to be ready for me for another five years. That was about three years ago, and it took just a year."