Working comedians — the ones who aren’t famous yet — tend to take whatever gigs they can get. Sometimes that means half-empty bars, or coffee shops or off-nights in a tiny comedy club.
In Steven Lolli’s case, it meant a clothing-optional resort in Land O’ Lakes 10 years ago.
(Michael Murillo/Staff Photo)
“It was one of the worst shows I’ve ever had in my life,” he said, recalling the scene at Caliente Resorts off Land O’ Lakes Boulevard, with a smile.
Lolli had been doing comedy about eight years at the time, and the Gaither High School graduate had returned to Tampa to set up some shows. Not one to turn down work, he tried a nicer, more approachable style to his comedy. And the crowd wasn’t buying it.
“The crowd was bad and I was bad,” Lolli said. “I should have been my angry self.”
What a difference a decade makes.
Lolli’s back in town, but he’s not trying to win over any skeptical crowds. Instead, he’s bringing his own following to the Carrollwood Cultural Center at 4537 Lowell Road, for his “High Class Poverty Comedy Tour” on Aug. 30. And he’ll be his angry self on stage, because it’s taken him pretty far in his 18 years as a stand-up comedian.
Lolli didn’t give anyone there the impression he would eventually make a career out of telling jokes when he graduated high school, and he headed to the Orlando area soon after to attend the University of Central Florida before making his way to Los Angeles. It was there in the California sun he gained a reputation for fitting in at venues where he’d look out of place.
Lolli began frequenting comedy clubs where the performers and audience were overwhelmingly African-American. He might be one of the only white people on stage — and the only Jewish person in the room — but he was something else, too. He was funny, and the crowds responded to him.
Nationally known comedian Katt Williams helped develop Lolli’s moniker, “The Urban Jew,” and eventually hired him as a writer.
Minority audiences appreciated his honesty and responded to his earnest delivery, Lolli said.
“I started talking about race. I started talking about Jews and blacks,” Lolli said. “One thing about the black crowd is they really respond to true emotion, when you’re really being honest.”
That response was a pleasant contrast to other clubs he visited, where politics and social relationships dictated who got to perform, and too many comedians wanted to mold their act into a television-friendly package. Lolli wanted to protect his edge rather ingratiate himself to the people who were the gatekeepers and could deny him stage time.
Performing in African-American clubs might not have looked natural at first glance, but it was a natural fit for his style and philosophy.
Cutting his teeth in tough rooms, and gaining acceptance from what could be considered challenging audiences, made Lolli more fearless in his comedy and more confident in his abilities. And while the 38-year-old could pass for a young executive on the street, it’s a different story on stage. His material is adult-oriented, salted with the kind of language that gives his rants emphasis.
But Lolli doesn’t simply rely on dirty words for shock value. His language is an extension of his thoughts and perceptions at that particular moment. While he has plenty of prepared material, he allows himself to veer off track frequently and create something original out of unscripted moments from earlier that day or while he’s on stage.
There’s a lot of risk with that method, and grabbing the microphone in front of a packed house without a clear idea of what you’ll say beforehand can be scary. But his real fear is not being true to himself.
“I’m more afraid to not say what I mean,” Lolli said. “It’s the most gratifying feeling to be yourself.”
It also can provide a career boost if things go well. Lolli once performed at an event honoring a cable executive, with many important agents and actors on stage and in the audience. It would be a perfect time to play it safe and not make fun of their industry, but that isn’t his style.
He came out aggressive with his material, got the audience on his side, and has received a lot of work as a result of that edgy performance. That included a 2012 guest appearance on the NBC comedy sketch show “Betty White’s Off Their Rockers.”
He’ll deliver more of the same at the Carrollwood Cultural Center, though he’ll have a lot more time to explore his thoughts and expand his material. He’ll also have his parents, Joy and Gerald, in the audience. They’re proud of his success and have taken note of his rising notoriety as the venue promotes his show.
They also haven’t seen him perform in years, but that doesn’t mean they’ll get the easy treatment from their comedian son on Aug. 30. In the end, they know he has to be himself.
“They’ll be all right,” Lolli said. “I might make fun of them, too.”
Published August 27, 2014
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