Josh Gondelman is talking now

We visit with the comedian as he tours.

Josh Gondelman wasn’t trying to hide the road from what he brought into the coffee shop, he couldn’t have anyway. Travel follows you to your table, man, nobody ever sits alone.

Josh is a comedian more often than an actor, a writer more than performer, so there wasn’t much point in obscuring what was out in front of us – giant bottle of water, hydration is key, an off-stage voice teetering somewhere between sotto and Patty Smyth mostly due to its re-introduction to the Midwest in December.

His manners were impeccable, but Gondelman’s best posture and voice were saved for that night’s performance at Zanies, the famed standup club in Chicago’s Old Town. This was his fourth show in five nights with another to come the next day, all snuck in during the tiny spot of year that he has off from the day job at HBO. Comic slash writer stuff.

Gondelman wasn’t trying to sell tickets to this table, it could tell where he’d been. Still, listen to the sort of words that came out of his mouth on a Tuesday that was slightly less cold than the Tuesdays that accompanied his tour from last winter:

“This is even a relief to be in Minneapolis, Chicago, Iowa City, Eau Claire …”

Other voices would trail off, but not Josh’s.

“I’m really glad that what I’m doing doesn’t just translate to New York City comedy clubs. Or,” because there is a distinction, here, “New York City alt-venues.”

Gondelman hunched toward this recognition prior to playing a show in front of giddy spots of ardent fans, thick with knowledge of the local public transit system and an appreciation for Gondelman’s eagerness.

They sat alongside loutish Irish tourists, dates gone both good and terrible, and the sort of young, urban professionals that the city used to just tolerate. All bent toward Josh’s stage in full view of freaky, Day-Glo posters of Richard Lewis and Jay Leno.

The comedian’s album Physical Whisper darkens the tape heads with oxide loss, but it still holds its hooks: Boston and The Cars had debuts like this. The hits went over a charm with a crowd that was excited for Josh to finish a story, but not because they wanted to go anywhere. The performer was aware of this.

The new bits swung with assurance, Gondelman in clear view of what was going to work on a Tuesday, an evening ages removed from the Sunday nights and Monday mornings that his work often dominates.

Gondelman is one of the writers behind HBO’s Last Week Tonight with John Oliver, and it appears that his confidence travels well, buoyed by the blank page on stage.

“The benefit of performing, the thing that keeps me doing it and the thing that I enjoy, is that I get to do whatever I want.

“That’s the pleasure of standup, for me, there’s no confines of the structure of a different show that dictates the subject matter. Or the tone of it.”

That doesn’t mean that the extra layers between brain and audience, a distance drawn greater and greater as the era reveals its daunting self, can’t bring an extra kick.

There’s no getting away that extra “layer in feeling pleased about” something your “bosses liked first,” Gondelman relayed, a trip held in as high esteem as the thrill he gets watching Oliver nail a line that Josh and his co-workers had a role in helping keep safe.

If he’s cool with either hanging onto or living with a joke throughout the entirety of the workweek, with more politicians and crooks adding more and more re-tweets and shares to the entire mess, then Gondelman is certainly as serene as a vicar after two swipes of wine when detailing his long-studied set in front of a laughing crowd.

Brian Stack is famous for doubling you over with his on and off-screen work on all three variations of Conan O’Brien’s television shows, his inimitable dry drive is all over the Late Show with Stephen Colbert, and he cops to what we’d all presume from the outside, in times like these.

“The downside of the fast turnaround is that you have to crank out the material very quickly, which can be a bit stressful at times.”

Brian finds solace, as writers often do, in something he is terribly ill-equipped for.

“The upside is that you don’t have time to agonize much over it or second-guess yourself, which is actually a specialty of mine.”

Stack, an improv legend sprung from the same Old Town neighborhood Gondelman just headlined three nights in, will probably be the first to tell you the stage offers no time for agonizing. Josh’s set reminded us of the distance you damn well better have from Nervous Time to the tick in which the doors open.

In a life clearly spent torturing himself over the details of comfort assured for everyone but himself, Gondelman is absolutely at is most charming when on stage. He is in full control even while typically performing in the gait of a Guy Who Really Doesn’t Want to Help Gather All This Kindling.

For those that follow the man on Twitter, the idea that he might outstrip his presence on that website with appeal in action might seem like a stretch, but consider how much time you’d expect a thoughtful fella like Josh Gondelman to craft a tweet.

Now, consider how much time he’s taken to craft what he’s going to say in front of a bunch of really nice people, after most of them give him money.

“Josh Gondelman is the comic that Gotham needs,” insists comedian and writer Aparna Nancherla.

She’s no stranger to filling nights in New York clubs while waiting out the days it takes for your TV joke to hit the air, and she wasn’t finished.

Aparna’s knowing eyes wetted in the face of an unrelenting 22nd story view, her trench coat ruffled in the glare of a breeze that by this point she had warmed to long enough to call familiar.

Again she stared into the cityscape that she promised herself she would never, ever, tire of.*

(*Aparna asked me to write all this.)

"Josh Gondelman is good for New York,” she clarified, “because he is the comedian Gotham needs, not the comedian Gotham deserves.”

So, maybe he isn’t a wine-soaked vicar. Gondelman was a schoolteacher, mentioned in his act in bits both sparkly-new and on tape, and because it’s all over the way he holds a microphone, it came up.

“I think there’s a lot of overlap,” after I tried not to ask the same teacher-to-comic question he’s already heard far too many times. He made it better.

“I think that’s one of the reasons why there have been so many comics that have been teachers.

“It’s about communicating ideas to groups of people that have various levels of interest in absorbing the ideas. That’s the key crossover. Meeting people on their level. Figuring out how to give a group of people – both in preparation and through real-time adjustments – what they need.”

Alison Abrams is a friend of Gondelman’s, but also a podcaster who has glared through quite a few comedians in her time.

“He’s an incredible listener, which not every comedian is.”

“Even when there’s an urgency to what he says,” Abrams explained, “there’s still something of his aura and demeanor that’s retained from” whatever the heck Gondelman had to do when stepping around that preschool, speaking over listeners stuck staring at his ankles.

She went on.

“Even if you’ve only exchanged a few sentences with him, you come away with this real, rare impact of an incredibly genuine and positive man.”

Somehow, Gondelman gets past security.

Nobody folds its arms better than a room full of preschoolers, save for perhaps the cellar dwellers in a comedy club. Nothing clicks harder than a bored right thumb on Twitter, and yet we slowly read Gondelman providing assurance that would melt the heart of both Bart and Lisa.

Monday morning cubicle-chucklers look for every reason to tap away from the Oliver video that still has 11 minutes left on it, and yet far too many for capitalism’s sake stick around until the end. That’s not benefit earned through knowing one of the writers is a swell guy, or even knowing who wrote any this stuff. It’s because the payoff is worth it after the delivery aligned so well with the original spirit.

You used to have to work harder for these sorts of laughs, but in a time where they’re delivered to your phone for free, Gondelman makes the trip worth it.

ZANIES

Toward the end of the sort of Comedy Boom that put the photos on the wall at Zanies, Dennis Wolfberg started to become ubiquitous. On weekends, on cable, ready to draw your attention and keep it:

Wolfberg was a schoolteacher as well, he hit Letterman enough times for us to notice and for clubs in the Midwest to fill up. His sets translated in every way imaginable, kids at home blindly rolling at the same stuff that the young, urban professionals in the cable TV audience seemed to enjoy.

Wolfberg passed away after a fight with cancer in 1994, just as outlets for his sense of story began to dry up on live stage. Those outlets had just begun to flourish on television, though, and Wolfberg was in talks until the end.

There’s a patience in this realm that, to outsiders, appears extraordinary. Gondelman has developed a tone that outlasts an anecdote, his delivery remains consistent due to the confidence in what’s about to unfurl.

That’s not unique to standup comedians, any good one has that, but Gondelman’s approach can’t help but remind of his resume.

You do it yourself, no matter what 20-something gig you have in your own history, when it comes time to challenge muscle memory. You’re going to fall back on those fundamentals, even if you learned them all while violently hungover.

Of course, that’s not why you go out to see Josh Gondelman, or any other standup still drawing two-drink diamonds out of lessons learned from the bad credit years. The jokes are great, but anyone can make fun of the old day gig.

What’s great about Josh is the lesson plan. It’s clearly in place, and it’s better on stage.

“I can do whatever I want. It’s such an exciting and gratifying outlet that I have. To explore at my own pace, and my own time.”

Josh Gondelman appears at The Virgil in Los Angeles on Dec. 12, and in San Francisco at Doc’s Lab on Dec. 13.  Follow him on Twitter for links to upcoming dates in Philadelphia and Washington D.C.