HE TELLS A JOKE—something like “Have you seen this show on Lifetime about that woman?”—and then there’s that look, that thousand-mile stare, his brow furrowed, his mouth pursed as if he just realized he forgot his mother’s birthday. It’s not the look you expect.

He tells another joke—something like “When you look like me, it’s hard to get a table for one at Chuck E. Cheese.” The crowd laughs, and Zach closes his eyes. He lays his head on the piano, runs his hand through his hair. He seems weary, like each joke exhausts him. It’s almost like he’s trying not to engage the audience. But his deadpan has the opposite effect; it brings you in closer—the same way Mitch Hedberg could bring you in by staring at the ground.

What’s he doing?

“I know what you’re talking about,” Zach says. “But I don’t really know what that is. Maybe I’m basking in the awkwardness. But I think it’s sort of like, There’s a joke. Accept it if you want to. I’ll wait and then move on.” 

That makes sense. In his pursuit of humor, Zach goes to great lengths: At a recent show at Irving Plaza in New York City, he stripped off his clothes to reveal a Little Orphan Annie costume, in which he lip-synched “The Sun Will Come Out Tomorrow” while shuffling through written jokes on a drawing pad like “I call my balls the Bush twins.” But despite this willingness to go all out, he doesn’t pander; his act can be seen as a testament to courage, not desperation—a willingness to try anything and disregard failure.

Patton Oswalt, who included Zach in the Comedians of Comedy productions, has said: “Zach is probably the least needy of all of us. It’s not so much that he’s in his own world, but he’s so formed in what he thinks is funny. It’s almost like a guy who is so comfortable in what he’s doing that it naturally draws people in.”

Perhaps this resolve is the result of years spent struggling in New York, where he got his start in the back of Hamburger Harry’s, a small place on West Forty-fifth Street. He spent years bombing with jokes like, “A girl told me I could sleep on her futon. I’ll tell you what I told her: ‘I don’t sleep on anything that rhymes with crouton.’ ” On good days, he’d make fifteen dollars for a set, five of which would go toward rent, three toward two forty-ounce bottles of beer, and the rest toward food. On the side, Zach worked as a busboy in a strip club. He also worked as a nanny for a child that demanded things by threatening to fabricate stories of how Zach molested him.

Through all of this, Zach told jokes, let people accept them if they wanted, and then moved on. After a few years, he moved on to Los Angeles, got a part in Boston Common, got a few parts in bad movies, and kept telling jokes.

The moving-on part is key. Although many well-known comics are happy to coast through with the jokes they’ve been using since 1992, Zach refuses. “If a joke has been seen on television or wherever,” he says. “I won’t do it as much—or at all.”

Instead, Zach writes new material—on napkins and matchbooks—and at the end of the day he empties his pockets and arranges what he’s going to try out.

Two weeks prior to the Irving Plaza show, he gets an idea while waiting for a train from Brooklyn to Manhattan. “It’s so dumb,” he says. “The train was late this morning, and I felt this urge to yell out to all these hipster kids in Williamsburg—just yell out like a little kid—“The choo-choo is coming!” Maybe I’ll do that. I don’t know.”

When he tells you about it, you’re not sure how it’s even a joke. You have your doubts. But sure enough, partway through the Irving Plaza show, he begins, “Sometimes when I’m waiting for the train”—and you know what’s coming. You’re even a little nervous as he describes seeing the first glint of light from the headlamps down the tunnel. “Here comes the choo-choo!”  he shouts. The voice is more a cartoonish hillbilly than a little kid. And he grabs his penis when he shouts it—to show just how exciting the train is.

It works. Heads in the crowd tilt backward almost in unison, coughing their amusement to the rafters. Three girls in the VIP balcony exchange looks as they shriek with laughter. The stone-faced security guard by the door smiles and shakes his head—as if he doesn’t want to think it’s funny but can’t help himself.

Of course, not everything works. At a recent show in Los Angeles, a comment Zach made provoked audience members to throw ice cubes at him: “I was kowtowing to this one table,” Zach says. “And they were eating it up. And I’m not going to tell you what I said, but basically right after I’d won them over, I turned it around and said something completely horrible. So they started throwing ice cubes.”

Either way, he tells a joke, lets you accept it if you want, and then moves on.

In addition to his consistent willingness to try new material, Zach also enjoys interviewing members of the crowd. “It’s much more interesting to go off the written material,” he says. “It’s kind of selfish, but that’s what I enjoy doing.”  The without-a-net openness of this kind of interaction yields moments of brilliance as well as tormenting awkwardness. And in his new DVD, Live at the Purple Onion, you see both.

Of the DVD, Zach says, “I wanted to capture a more typical show. I wanted something less polished. Although I’m never polished anyway.” To this degree, the DVD is a success; there is nothing polished or sterile about it. Zach doesn’t “vomit out jokes” the way he said he had to with his Comedy Central Presents performance from 2001. Instead, the shows, which contain a balance of recent material and typical crowd interaction, are broken up with footage of Zach offstage. There’s a scene in which he’s introduced to perform while he’s still at a restaurant down the street; there’s a scene in which his van breaks down. You get a full glimpse of Zach’s disheveled charm.

But there is also a more sobering side to the presentation, signs of premature deterioration. Zach has put on weight. When he removes his sport coat during a performance, his polo shirt resembles a trash bag filled with sand, and he jokes: “I went to the shirt store and asked, ‘Do you have anything to highlight my alcoholism?’ ” 

The crowd laughs, but you have to wonder, especially as the DVD continues and there’s scene after scene of him drinking beer, then wine, and empty glasses of various shapes and sizes appear on the piano. At the Irving Plaza show, he alternates between a glass tumbler, a wine glass, and a coffee mug.

There are moments in the DVD when the crowd work drags on. The more it does, the more he begins to insert self-conscious narration. He assumes the voice of a viewer, “Yeah, we went and saw Zach. It was good at first, but I don’t know—he’s losing his fucking mind.” Then there’s a cut to a scene in which he comments on the precariousness of his sanity, the “fragility of the human psyche.” You have to admire his decision to include this footage. It makes the DVD more complex—gives it the feeling of a documentary rather than some kind of greatest-hits compilation.

Also edited into the mix are clips of an interview that NPR’s Brian Unger conducts with Zach’s twin brother, Seth. To create this character, Zach shaves his beard into a mustache and takes on the persona of an effeminate high-school football coach and youth minister from the South. He’s great at it because he’s been playing the character for more than 20 years.

“Me and my friends growing up would all do these Southern effeminate guys,” he says. “There’s something funny about it because Southern culture is emasculated in a lot of ways. I used to do that character all the time for my dad.”

In high school, Zach developed the character even further, into an effeminate racist. “There was this black guy named Antoine in my art class, and I used to do it for him, and he told his friends to bump me in the hallway. So they would bump me in the hallway to release this character, and I would go on this diatribe with the black kids about black people, and they would just die laughing because they knew I was making fun of the rednecks we were surrounded by.”

When asked why he thinks the character gets such a warm response, he says, “There’s something funny about someone who’s effeminate and who has probably been made fun of and been discriminated against to go and discriminate against other people for their differences. It’s such a weird, layered juxtaposition.” 

The majority of Zach’s characters seem to spring from this fascination with juxtaposition, with how opposing motivations and insecurities can create absurd, conflicting behaviors within a person’s identity. He has the Timid Pimp, the Pretentious Illiterate, the Self-deprecating Nuclear Physicist.

On a greater scale, paradox is a theme that runs through his whole act: the way he pairs a joke like “My grandma treats me like a rock star—I guess that’s why she lets me sign her tits”  with grave vamping on the piano; the way he finishes each joke with that vacant stare; the way he can lip-synch “The Sun Will Come Out Tomorrow” while shuffling through a joke like “I hope Dick Cheney’s faggot daughter gives birth to a faggot daughter.”

And this extends even further, to Zach’s own conflicting intricacies—intricacies you’ll never understand: There is nothing simple about the way the crassness of his humor doesn’t flush with the number of references he makes to his family, the stories that involve him telling jokes to his dad or putting on performances with his cousins in his hometown of 2,000 people.

In the same way, it’s difficult to reconcile the knotty logic of statements like “If people really like me, I like to turn on them.”

At another point, Zach says, “When my friends bomb, it’s one of the greatest things. I love to watch.” But then he moves on to describing his close friendship with a ninety-two-year-old man named Albert: “He built this one-man band and would come over and entertain me. He’s done the Jimmy Kimmel show with me. He’s ninety-two and feisty and very touchy-feely with women. But he’s just the greatest to have around.”

It seems as though Zach’s always trying to fight the momentum of situations—hedging the ebb and flow—by turning his back on the obvious, easy things and pursuing avenues he’s not sure about.

After the New York City show, Zach is backstage drinking wine when fellow comedian Eugene Mirman stumbles into the room and says, “That was really, really amazing.”

“Thanks,” Zach says. “We’re gonna go drinking later,” and then he points to the back room. “Everybody’s back there.”

Eugene picks up on the fact that he’s interrupting an interview and says, “Yeah, we’re gonna go in there.” But then he lingers a moment.

Zach says, “How long is it gonna take you to go back there?”

Eugene smiles. “Slightly too long,” he says, and then starts stroking Zach’s hair. “It was really good. Really funny. I’m proud of you. So, so proud.” 

“Yeah, yeah,” Zach says.

Eugene continues, “Proud of you.”

“All right, Eugene,” Zach says, swatting at Eugene’s hands.

Eugene steamrolls through Zach’s attempts to deflect him. “You made…you made…”

“You’re such a drunk,” Zach says.

Eugene goes to leave, but now Zach has thought of something. “I really took it to Dane Cook,” he says in a sarcastic way. (In the show, Zach had joked “I saw Employee of the Month the other day…it wasn’t as good as I thought it was gonna be.” Then he ended the show with a drawing board that read “Kill Dane Cook.”)

Eugene agrees. “Yeah, I hope he myspaces you.” 

Zach says, “I think he knows I do that bit, ” ’cause I met him and he was like, ‘So, we officially meet.’”

“Really?” Eugene says, “He talks like Darth Vader?”

“Yeah,” Zach says. “He does. And he has the same skin as Edward James Olmos.”

Eugene doesn’t say anything, doesn’t have anything malicious enough to trump that. He stammers, “Uh, well. Let me—” 

Zach lays it out there again, slower, “Edward. James. Olmos.”

“Okay,” Eugene says. “Sure. Good luck.”

Zach says, “All right, Eugene. Hey, do you want to sit in on the interview?”

“No no,” Eugene says, and then goes into the back room.

The second time he says “Edward James Olmos,” Zach looks for recognition. You could chime in with the name of some other pitted icon. Bukowski maybe. Or Tommy Lee Jones. But you don’t want to. Zach is better than that. Taking shots at Dane Cook is cheap and pointless. Like hipsters complaining about Starbucks. Or a yuppie complaining about hipsters.

But as soon as you’re ready to be bothered by it, you realize Zach’s moved on. He talks about a 60-acre farm that he bought in North Carolina. These days, he’s grooming the land, and many of his new jokes come to him while he’s driving his tractor, chewing tobacco, and daydreaming. His goal is to put cabins up and start a nonprofit writers’ retreat, maybe even a music school.

When asked about his motivation for doing it, Zach says, “Since I was a kid, I’ve always wanted to have some kind of cult.”

There’s a good chance he’s only half joking.

A twentysomething walks into the room and starts telling Zach about his favorite joke. Zach laughs and says, “It’s so dumb.”

In a second, he can shift gears from having cult-building confidence to extreme modesty—almost a shyness from praise. When you talk to him, he prefaces almost every successful joke or new idea by saying, “It’s so stupid” or “It’s dumb” or “It’s just sillyness.”  In the same way, he denies the altruism behind starting this nonprofit organization: “It’s selfish,” he says. “It’s therapy for me.”

The conversation ends, and before you leave, you turn back one more time. Zach’s moved on. A photographer is there taking pictures, asking Zach to stare at himself in a mirror. Zach does as he’s asked, then moves on, to the back room to be with his friends.