The first time I saw Todd Snider was with a couple thousand chatty, wine-drinking, picnicking Portlanders on a sunny summer afternoon at the Oregon Zoo. We were all waiting to see folkster Greg Brown when this scruffy-looking, blond-haired, barefooted young dude comes sauntering out, mutters something at the mic and starts chopping away at his acoustic guitar.

Nobody listens right away; they’re waiting for the main event.

But about 16 bars into the first number, people stop foraging through their picnic baskets and, one by one, swivel toward the stage. I was talking to my girlfriend. I told her I was stressed. Said I’m goin’ off the deep end, she said, God, for once give it a rest. A couple of laughs and hoots from the crowd. Mothers with children forsake the monkey house and head for the stage to see what’s going on. We’re all waitin’ in the dugout, thinking we should pitch. How you gonna throw a shutout when all you do is bitch? …I can’t complain.

All the chatter that had been percolating through the crowd stops. People are clapping to the beat, yipping and yahooing, picking up the lyrics and singing along to the chorus. Half an hour later, at the lurching buildup of “The Ballad of the Kingsmen,” he’s got the whole damn zoo crowd eating from the palm of his hand, waiting on bated breath for the next verse and exploding into a cathartic anarchy of applause as he swoops into the song’s climax. When he finishes, the crowd swamps the CD table.

Call it the Snider Effect. It’s why one of the guy’s own idols, the Texan troubadour Jerry Jeff Walker, said Snider “won’t quit ’til he gets the audience. And he always get the audience.” It’s why John Prine said he’s the hardest act to follow (I could tell you maybe two of the songs Greg Brown played that night).

Over the last 15 years, the Oregon-bred Nashville transplant has developed a rabid following for his exemplary live shows. A masterful, folksy storyteller with a whiskey-torn Southern drawl, Snider’s Arlo Guthrie-esque comic timing is impeccable, as he stretches out and speeds up his songs to serve his improvisational punch lines, then soars over what seem like whole minutes of laughter with a rush of guitar and a wailing harmonica line. He’ll bring his show to the Big Easy on Tuesday.

Speaking from his tour bus in Florida, Snider tells The Inlander there’s a secret trick to winning the audience over like that — but if he tells me, Jimmy Buffett will kill him.

The real trick is his one-two punch. Snider lures his audience in with a pocket full of straight-up humor songs — the ever-popular “Beer Run,” 1994’s “Talking Seattle Grunge Rock Blues” — and then knocks them down with tunes like “Broke” and “Tension,” songs that use that humor to cast a delicate glow on some of life’s darker, sadder places.

And Snider knows those darker places. A troubled kid in school, he spent 10 years or so after graduation as a “sofa-circuit person,” sleeping at friends’ houses and trying to make ends meet. At the end of his teens, he took up residence on a couch in Austin, Texas, where he saw Jerry Jeff Walker play for the first time. “Shit, I can do that,” he recalls thinking, on his live record. He bought a guitar and started writing and playing obsessively, quitting his day job to make music full-time. Nursing chronic back pain, he got hooked on pain pills, particularly OxyContin.

On his way from Austin to Memphis — where he got his first regular gig, inked a deal with Jimmy Buffett and started putting out records — then, ultimately, to Nashville, Snider lived with and fought against his addiction to pills. Twice he was checked into rehab, swearing off drugs as he left.

When his friend Skip Litz, the “unofficial mayor of East Nashville,” died of stomach cancer in 2003, “things just seemed like they spiraled out of control.”

In late 2003, Snider stood on stage in Tampa, Fla., at the onset of a lunar eclipse, singing “Waco Moon,” a song about a friend’s lethal overdose while on “the drug that killed my friend,” he says in an interview. “I was on enough of it to die in that moment.” Snider woke up in rehab a week later, with little recollection of his trip to Florida. It was his most serious bout with the painkiller.

All of this — the drugs, the addiction, the rehab, the relentless touring, the back pain, the arthritis in his hands, getting older, watching his friends die — shows up in 2004’s East Nashville Skyline, Snider’s most challenging and critically acclaimed album to date.

The record opens with five mostly autobiographical tracks, including a candid prologue about the state of his life, a tribute to Litz and an eerily resonant cover of Fred Eaglesmith’s “Alcohol and Pills.” It opens into a kind of proletariat manifesto, with a series of songs about the plight of the poor and disenfranchised (the kinds of people who make up his beloved East Nashville), before ending in a couplet about suicide and rebirth.

Throughout, Snider deftly balances humor and trauma, tragedy and absurdity. “Play A Train Song” sounds less like a funeral for Litz, and more like a maudlin celebration. In “Sunshine,” after throwing himself from a building, the narrator is told by a menacing St. Peter, “I’m going to break every bone in your body” before being sent back to Earth to try again. The guy’s such a failure he can’t even die right.

When we talk, Snider is preparing for a show in Florida. He sounds positive, upbeat in a tired kind of way. He’s living better, he says. He’s off the pain pills and hopes to remain so. His tiresome road life, he suspects, has a ways to go yet. Still, he says wryly, self-effacingly, echoing the lyrics from that first song at the Oregon Zoo show in 2004, “When I talk about singing and stuff, I would feel funny complaining. It’s hard to be a f–in’ construction dude, too.”

Todd Snider plays with special guests, the South Austin Jug Band, at the Big Easy on Tuesday, April 26, at 8:00 pm. Tickets: $15. Call 325-SEAT.