Ike Reilly learned to play guitar while working in a cemetery. He’d held that job every summer through high school and college. He started by cutting the grass, and then moved on to digging graves. He buried a lot of amputated appendages because, he claims, “Catholics do that.” When he was 18, he had to set the stone for his best friend, who was killed in a car accident.

The job offered a lot of downtime–warm, stagnant days were spent drinking Pabst and shooting off firearms in an adjacent dump. Occasionally a coworker, Bill Fanelli, would teach him chords. After work the two would go to Fanelli’s house, where Reilly would write words and “bash something out” on a four-track tape recorder.

Reilly left Libertyville to attend Marquette University. He enrolled in the Marine Corps officer training school, and after graduation wasted a few months studying for the LSAT. Then he moved to Chicago and formed a band with Fanelli called the Eisenhowers. Starting with seven songs, they began playing in Milwaukee, where Reilly still had friends from college.

In 1989 Reilly took a job at the Park Hyatt on Chicago Avenue. Starting in room service, he moved up to bellman. At first he worked nights, but soon he was on the day shift. Eventually he was promoted to doorman, a position he liked. “It provided a good living and they’d let me take time off, go away with the band, anything I wanted.”

He quit the Eisenhowers to join the Drovers. For five years he led a group named Ike Reilly, Community Number 9; his band mates included Mars Williams of Liquid Soul, Phil Karnats of Tripping Daisy, and Aidan O’Toole of the Muck Brothers.

Lou Dybel, a bellman at the Park Hyatt, recalls seeing Reilly in action. “I remember when he let this homeless guy onstage,” Dybel says, sitting next to Reilly in a north-side diner. “He was performing a solo acoustic set and after a few songs Ike was bored and there was this homeless guy and he just let him onstage–gave him his harmonica and the guy started singing.”

“I think I caught something off that harmonica,” Reilly says.

“First time I ever saw Ike stop in the middle of a show and say, ‘All right, that’s enough of that shit.'”

Reilly looks back on those days with a hands-over-the-eyes embarrassment. The period culminated in his lone recorded venture: a self-produced CD with Community Number 9 released in 1992. Calling it “unhip,” he regards it as a reflection of his dissatisfaction at the time. He quit the band in 1995, turning his full attention to his career as a doorman. Then it was announced the hotel would be torn down, beginning in January 1997.

“I just said, ‘Fuck!'” Reilly says. “That was a great job. That’s where people would meet me. They’d come to the hotel to talk to me. Band members, friends, club owners, whoever. That’s where you’d find me.”

Wanting to get involved in film, he became a freelance production assistant. In early 1997 he opened his own recording studio with engineer Blaise Barton called Diamond City. They spent their first year attracting business, taking money from “anyone who wanted to record anything.” Reilly continued to write songs and started recording them a year later with engineer Ed Tinley, who had worked with Liz Phair, Smashing Pumpkins, and R. Kelly. This marked the first time Reilly recorded without a band, depending more on samples and loops, starting with an acoustic take and then “building the song out.”

Last month Reilly called Daniel Nix, the brother-in-law of a friend. Nix had movie connections, so Reilly had sent him a few film treatments–they weren’t long, one, maybe two pages at most. Nix was impressed enough to ask, “What else do you do?”

Reilly replied he’d been recording “some songs”–actually, between 30 and 35–and Nix asked him to send his CD. Nix quickly responded, offering to shop the CD around Los Angeles. Not three days passed before Reilly received a call from a start-up label. They wanted him to sign a contract immediately; they promised to fly him out afterward.

Choosing to go to Los Angeles first, Reilly set up a couple of other meetings, including one with Virgin Records. On a Saturday in early November he was hanging out on the beach with some friends. They were listening to his CD when a woman approached. She asked if it was his own music, and he said yes. She told him she really liked it, and then asked where he was from.

“I’m from Chicago,” Reilly said. “I’m here to meet with some people from Virgin and some other people.”

She told him her fiance was best friends with Mike Simpson of the Dust Brothers production team. “He’s really the shit in this town,” she said. Finding a pay phone, she called Simpson and told him she’d met a guy named Ike Reilly, she loved his music, and the two of them would “really get along.” Simpson asked her to messenger the CD to his office on Monday.

That Tuesday Reilly’s meeting with Virgin went well. He called his wife, Kara, to tell her the news. She said “great” but a man named Mike Simpson had been calling–he wanted to talk to Reilly right away. Simpson had been leaving messages everywhere (saying, cryptically, “I got your message, George”). After a round of phone tag, Reilly headed for another scheduled meeting–this one at a manager’s house in the Hollywood Hills.

He hoped to enlist a manager of some stature to help achieve his goal–a legitimate recording contract and a CD of which he could truly be proud. He found Tom Atencio’s house just under the Hollywood sign. Nix was there, as well as Atencio’s partner, two assistants, and an intern. Reilly and Atencio began to talk about music in general and more specifically “how everyone’s full of shit.”

“Are you going to play?” Atencio finally asked. “Do you have your guitar?”

“I have it in the car,” Reilly replied, after realizing Atencio wasn’t kidding and actually wanted to see if he could perform.

Our most important moments often find us fumbling. For Ike Reilly, there was no buffer. He wasn’t onstage. There would be no one talking over the music–just a small group of people listening to see if he had some worth.

“God,” he said to himself walking out to the car, “this is really going to be awkward.” He grabbed his sunglasses as well as his instrument, figuring that if he didn’t have to look at them directly he might do well.

Sitting beside a backyard pool, with the Hollywood sign at his back, he played an acoustic version of a song called “Marine Corps Daydream,” and then he waited in silence for some response. At last, Atencio spoke up, saying “I knew he could fucking play.” Approving laughter came from the others.

Atencio told Reilly his songs didn’t fit into any genre (they’re perhaps best described as a amalgam of punklike riffs with the heartening lyrics of a Merle Haggard), but he could still see the sentiment and foresight, “the vision” behind it. He called Reilly an original. Reilly then mentioned receiving a call from Simpson.

“You did?” Atencio said with surprise.

“Yeah,” Reilly said. “I’ve got three messages from him.”

“Really? Do you know about Mike Simpson?”

“I know he’s a producer.”

“Well, yeah, he’s a producer,” Atencio said. “But he’s produced the Rolling Stones, Beck, Hanson, Ton-Loc, the Beastie Boys–he did Paul’s Boutique. He just did the music for Fight Club.”

“I think he wants to meet me,” Reilly said.

He finally spoke to Simpson on a pay phone in a Best Western coffee shop on Sunset Boulevard. Simpson asked where he’d be that evening. When Reilly replied Santa Monica, Simpson said he’d be in a studio there–could Reilly stop by? Reilly said no. He was tired and hungry and had no intention of hanging around a studio. Simpson said OK, but asked Reilly to call to at least let him know where he’d be.

Where Reilly ended up was the Broadway Deli at six or seven that night. It was already dark, and Simpson told him to hold tight–he’d be there in five minutes. Sure enough, a man in his early 30s showed up. He was wearing a beard, shorts, and sandals, and had “scruffy hair” and “a totally warm-looking face.” When he walked through the door, Reilly said he knew two things: first, it was Mike Simpson, and second, they’d soon be working together.

Over dinner, Simpson said he was an A & R man for Dreamworks. He was in charge of his own label–Ideal Records–through a joint venture with Disney. He said he’d been listening to Reilly’s CD for two weeks, but he had no idea who he’d been listening to. He had mysteriously received a copy of the CD labeled “George.” Simpson went on to say he’d help Reilly get signed to a label and, without hesitation, “I want to produce your record.” Feeling lightheaded and a little disoriented, Reilly went to call his wife. She had gone to bed early, and when he woke her up, as if on cue, she began to cry.

“You never think this is going to happen,” Reilly says. “It happens to the other guy. You know, I hadn’t even been approaching these songs as if it would happen. It’s amazing.

“If you had to pick a producer right now to get recorded by and be on this label as a singer-songwriter–this is him. I mean, anything short of this now is a disappointment.”

Since then, Reilly and Atencio have secured a firm commitment from Simpson to produce Reilly’s next album, though no deal with a particular label has been reached. Next month Reilly is scheduled to perform live for 45 minutes on the National Public Radio program “Morning Becomes Eclectic.” All of this puts Reilly on the cusp of something great–fame, perhaps, but also a life lived solely by his art, a goal he says he’d always longed for but somehow felt was inappropriate.

“I’m a guy that went to college that should have never gone to college, that should have pursued music from the time I was 13 but didn’t have the balls to do it because people expect you to go to college, get a job. I came from a place where that just wasn’t what you do. You don’t write songs–that’s folly. Honestly, I feel guilty about it. I feel like I’m getting caught beating off. ‘Oh Christ, you got me.'”

It’s a fitting sentiment from a performer whose best songs provoke a kind of lyrical understanding, as if we’re seeing life from a familiar angle yet we’ll never feel quite the same way about it again. Neither nostalgic nor dismissive, he settles for an uneasy alliance between the two. “I guess some of my songs are about weakness, cowardliness, pussies like myself,” he says. “I’m working on a song now about a couple. She’s got cancer, and he’s lying to her about how good she looks. But it’s veiled in a lot of poetic imagery. ‘As the angels rip your flesh, guiding lasers from their wings, we didn’t sing any sad songs. I’ll be a liar to you now, as your daily idol waits. You looked cracked but all right. Your eyes look fine. Your skin still shines.’ He wants to keep her beauty to himself, but then he wants to layer her with shellac. It’s kind of funny.”

When asked about the future, Reilly says, “It’s not scary. I mean, fuck, if there’s one thing I can do, it’s this. I’d say I can’t be a marine or a lawyer or a doorman or a grave digger, but I can do this. There’s no question I can do this.”

Art accompanying story in printed newspaper (not available in this archive): photo/Nathan Mandell.