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More than music or theater, standup comedy is a medium where your personal identity goes under the spotlight. And, unlike those other two art forms, it can also sometimes be the last gasp of homophobia in the entertainment industry.

So you could understand why Jordan Wieleba waited five years into his standup comedy career to publicly transform it into her standup comedy career. “I was petrified,” Wieleba remembers of coming out as a woman not only to her family, but to a community of fans and colleagues who’d spent half a decade getting to know Jordan-the-boy. “For some people, it’s still taboo. People have called me a pervert, or called it a fetish. But what I do with my act is try to educate people through humor, show them we’re not all Crying Game and Silence of the Lambs.”

Wieleba’s act is far from an after-school special about why you should be nice to transgender people. Her jokes are timely and universally relatable. Laughs are often sparse through the first minute of her set, many suburban straights writing her off initially, assuming there’s no common ground for a joke to take root. But in no time she’s won them over, succeeding in a double duty of cracking up an audience (a task in itself) and perhaps educating some patrons who’ve only heard about transgender people through Focus On The Family pamphlets.

Before Wieleba made the leap into comedy, he was a teenage boy living in the affluent Denver suburb of Greenwood Village. Moving into the city to perform in the locally renowned punk-band, Fourth Yeer Freshman, Wieleba was homeless for a time, living the rock-lifestyle of no-money, no-problem, before attending Westwood College – which she to as her “alma-doesn’t-matter.”

By this time the Denver comedy scene had picked up on the national alternative standup movement, which took the performances out of expensive comedy clubs and into rock venues, often the two mediums overlapping on the same bill. So it was a natural transition for both Wieleba and those who knew him when he stopped singing songs and began telling stories. The next transition would be a little less graceful.

“The first show I did after I came out was in Colorado Springs,” she said. “And the guy who booked the show didn’t know I now identified as a woman. I showed up in a wig and women’s clothes and he was like ‘what are you doing?’” Wieleba remembers the night fondly, though not without a hint of residual anxiety at the thought of introducing new material (always nerve-wracking for a comic) about a highly personal, highly recent sexual issue, all while inside the capitol of Evangelical homophobia.

“I’ve had some nights where the crowd just wasn’t into it. I’ve had some audible ‘ewws,’ or walkouts, which is no fun, but I do get good responses too … It’ll always be part of my act. I have to address it right away. It’s a goldmine for material, making jokes about people’s responses to it. One guy asked me how long it takes to transition, and I said a lifetime, and he misunderstood me and asked ‘so when you get your junk cut off you’re dead?’ And I was like ‘we’re not bees, man, when we lose our stingers we don’t die.’”

One large portion of Wieleba’s set is explaining the difficulty she’s had coming out to her parents, which occurred one year ago on Christmas morning. “My Dad’s a macho football fan and he had a hard time with it,” she said explained to a crowd one night at The Improv Comedy Club. “’Aren’t you going to miss your penis? That’s going to suck.’ And I said ‘Dad, look at it this way: Have you ever worn a really uncomfortable, really ugly, really small sweater – for 32 years?’”

In addition to her sketch comedy group, Fried Nothing, and a monthly showcase at The Bar, Jordan Wieleba has been filming a documentary on her transition, chronicling the successes and setbacks of coming out not only to friends and family, but to a public of strangers looking to laugh. Filming is scheduled conclude sometime this spring with her reassignment surgery, with a 2014 release date. “I struggled with this for so long. I was in the closet for 32 years. So I’m hoping this documentary will help others not be afraid to come out.”

Standup comedy has come a long way since the days of AIDS jokes in the early ’90s, allowing for cross-dresser Eddie Izzard and lesbian Tig Notaro to rise above the niche political support of their base and become the premier iconoclasts of their field. Yet while Wieleba and other struggling, mid-level LGBT comics have discovered within themselves a goldmine of authentic comedy material, they still, from time to time, must face the anachronistic machismo of sports bars and comedy clubs fans who aren’t always so welcome to what they have to say. And she continues to do it, night after night, slowly winning them over, not through guilt-trips, public service announcements or pamphlets, but through their shaking bellies. “It’s a long road,” Wieleba says, “and it requires baby steps. Which are a bitch in heals.”