Full-time comic: Jeff Oskay headlines Crackers this week 

On a dreary Monday night in Irvington, an unlikely comic is about to take the stage at Lazy Daze café's open-mic night: Jeff Oskay's three-year old son Elijah, who is at the moment hiding on the floor in the corner of the room, playing with dinosaurs and eating what appears to be a cup of whipped cream.

Then, he's called up onstage to join his father.

Of course, Elijah doesn't actually tell any of the jokes. His father is one of Indy's best stand-up comedians, and in a couple of weeks he will be headlining at the city's biggest comedy club (see infobox). But in this intimate coffee shop on the city's near-east side, Jeff is able to combine the two things he loves most — comedy and his son — in a brief, lighthearted performance. There is no CD recording or seats to fill or upcoming shows to plug on this Monday night; just a father and son, doing comedy for their own fun, like some parent-child tandems might play catch in the front yard.

The Oskays' performance brings down the house as Jeff reads "Elijah's" jokes for him, and mock-yells at his son for embarrassing him on stage, with the rage of a stage-mother forcing her daughter into a beauty pageant contest. Elijah turns his back to the audience and dutifully ignores his father; right on cue, with genuine apathy, letting out occasional groans of discontent.

Such is the comedic style of Jeff Oskay, who had no experience in theater before age 30, when he performed his first six-minute set at Cracker's open-mic night.

Seven years later, he is doing comedy full-time, touring the Midwest and writing for the Bob and Tom Show. That's not to say his life is any easier.

"This week I wrecked my car, fried my computer and just got a call from my landlord that I'm 14 days late on rent," Oskay says. "You know, just standard stand-up comedian shit."

Yet, the single father was more than eager to trade the steady income of his old job at a brokerage in exchange for happiness a few years ago, setting an invaluable example for his son in the process. "I'm working for myself, I'm doing what I love to do," Oskay says. "I want my son to see that no matter what your dream is, fucking follow it."

Jeff is a realist, though, and knows a time will come when he'll have some explaining to do. "When my son turns 15 and wants an Xbox, then it might be an issue," he says, enjoying a simpler time of fatherhood while it lasts.

"But right now he has no idea that I shop at Goodwill."

A long ride to the main stage

Crackers is not Carnegie Hall, but for thousands of comedians across the country — and even the globe — a headline gig at a club this size and tradition is the epitome of "making it." When Oskay headlines at the Crackers Broad Ripple stage Thanksgiving weekend, it will be with a mixture of gratitude and fear.

"It's terrifying as shit to me," Oskay says of headlining on the same stage graced by some of the modern icons comedy, such as Louis C.K. and Harland Williams. "That's way too much pressure; headliners have to fill seats and shit.

"I'm happy, but honestly I see it as just another opportunity to fuck up. Maybe that makes me a better comic. I'm always in fear of failure."

However nerve-wracking a headlining slot might be, it's an honor Oskay furiously worked on for over seven years.

It has literally been a long ride to the Cracker's main stage. Oskay was not driving when he first started doing open-mic comedy; his driver's license had been suspended due to piling up an astonishing 25 points in less than a year — all for speeding tickets. Consequently, he would ride his bike all the way to Broad Ripple just to do his six minutes, all for one simple goal: to emcee for one weekend.

It took two years to hit that first milestone, and Oskay readily admits that he was not a natural on the stage.

"I was fucking horrible for a year and half. I mean it was beyond horrible," he recalls. "The only reason I kept doing it was because I was determined to do one good six-minute set."

Eventually, Oskay delivered the one good set he'd been working toward, and was asked to emcee: then feature, then headline. This progression, which is standard for all comedians, is an indirect one and deceptively complex in nature.

It's not enough to be a good comedian, Oskay learned. You have to be a good emcee, then start over again and learn how to be a good featured act. Then, if the opportunity ever arrives — for 99% of comedians it doesn't — learn how to be a good headliner. Moving on to theaters and stadiums is another art form entirely.

"You can't be Louis C.K. starting out when you emcee," Oskay explains. "You can't make people think about politics or the way the world is. When you start to feature you can do a little more, but if you're featuring for Ray Romano you can't go up and do 9/11 material. You can't be the comic you really want to be until you get to start headlining; you have to earn that trust from the crowd.

"If the first comic going up is talking about some horrible topic, the crowd will just say 'Who the fuck are you to talk about this?'"

Honesty... with embellishment

Oskay is one of only a few comics in Indianapolis who's earned the right to talk about whatever he wants on stage. He did it by being painfully honest, and letting the most traumatic of life's challenges develop before the eyes of his audience. A couple years ago he was bashing his wife; now he bashes his ex-wife for cheating on him, all with a hilarious sense of angst and self-awareness reminiscent of Robert Schimmel.

"That shit was kind of a release, because I don't care if I piss off my wife," Oskay says, laughing. "I would never intentionally piss someone off with a joke, but my goal on stage is to be 99.9% honest... with embellishment."

Oskay has no interest in becoming famous, and developed a penchant for writing behind-the-scenes after consistently selling jokes to national headliners. Holding his son at the center of the universe, he is squeezing every opportunity he can out of this city.

He is a regular on The Matt Clemens Show, a locally filmed and produced internet show which features many of Oskay's nationally touring buddies, as well as some of the best Crackers regulars. He also does "The InterwebPodshow" podcast with Matt Holt, and is working on a one-man show for the Fringe Festival.

His most ambitious endeavor is a film he is currently casting: a mock-u-mentary in which he plays an aspiring magician. Oskay summarizes the film plainly: "It's basically about my stand-up career, but with shitty magic instead."

And, of course, there are the open-mic nights with Elijah, headlining gigs at Crackers, and all the dive-bar shows in between to keep Oskay doing what he loves, full-time.

"I'm broke," Oskay says, lifting a pint of Sun King, as he reflects on the two things he loves most: the craft of comedy and fatherhood. "But I would rather do this any day of the week."

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