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Michael Ian Black: 'I Don't Know What's Funny Most of the Time'

Comedian Michael Ian Black

If you love comedy, it’s a great weekend to be in Brew City, for this weekend marks the 12th anniversary of the Milwaukee Comedy Festival. And it gets even better, if you’re a fan of the Wet Hot American Summer film and Netflix series. For not only did the new season just start streaming, but one of its stars will be in town this Sunday, headlining the comedy festival: Michael Ian Black.

In addition to reprising his role in the Wet Hot series, Michael Ian Black is perhaps best known for his iconic work on MTV’s The State, Stella, and being a commentator on the popular I Love the 80’s, 90’s, etc. series. A multi-media talent, Black is also a prolific writer, director, producer, podcaster, and commentator. He’s authored 11 books, including the best seller, A Child’s First Book of Trump. In addition to Wet Hot, Black can currently be seen in TVLand’s The Gaffigan Show, and Comedy Central’s Another Period.

Despite having over 20 of years experience as a comedian, Black is relatively new to the world of stand-up.  He took it on as a challenge to himself more recently, and now has three comedy specials.

Black now brings his stand-up to Milwaukee. When asked why he chose to perform at the Milwaukee Comedy Festival, Black simply says, because he was invited. 

"One of the funny misnomers about a career in show business is people often say, 'why did you choose to do such and such?,' and the answer is because I was given the opportunity - so I did it."

What about his writing process? Well, for a professional comedian, he has a surprising answer:

How is the joke that I'm telling a joke that only I could tell? That, to me, is the critical question.

"I don't know what's funny most of the time. Everything strikes me as a little bit off-kilter, which makes me think I must be the one that's off-kilter. So I feel like I'm perpetually in a state of making observations to myself about things that just don't translate to the world. So it's a constant source of struggle and creativity to refine those things to a place...that people are understanding and recognizing."

That struggle is the very craft that he is perfecting as he hones his skills as a stand-up performer.

"I'm constantly trying to refine who I am as a stand up...I think it's a question that every stand up struggles with - what is my distinct point of view that makes me different? How is the joke that I'm telling a joke that only I could tell? That, to me, is the critical question."

Credit Simon & Schuster Books for Young Readers
Simon & Schuster Books for Young Readers

While writing for stand-up may be a relatively new endeavor, writing for children has been a natural progression. In fact, Black says writing a book for children is basically the same process:

"It's one to one - to me they're nearly identical. A good (funny) children's book...has a premise and you explore the concept...They're short-form, they have a kind of quick set-up and beginning, middle, and hopefully a satisfactory ending."

So, what kind of comedy is he a fan of? 

"I'm just a fan of the unexpected twist and going the place that I never expected to go. Any performer who can do that for me I just really admire."  Black cites Will Ferrell as a prime example - a performer who is just willing to commit to whatever character or premise he establishes, no matter how absurd. 

An an author of many books, including his memoirs You're Not Doing It Right, Navel Gazing, and his collection of personal essays, My Custom Van; Black is used to opening up his personal life to fans both on the page, as well as on-stage. However, that doesn't mean giving up his privacy. In fact, Black says it's entirely possible to remain open and honest with fans because in the end, the audience is there not to see a performer reveal themselves, but to see their own lives reflected back on themselves.

Ultimately...you're looking for a connection (with the audience), not a revelation about yourself.

"You can't appreciate the entirety of somebody, or you can't appreciate the entirety of even the moment that they're talking about without having a real kind of intimacy that you can't achieve through a book, or a film, or a stand up performance. All any artist can do...is edit those experiences to the best of their ability in hope that some part of it translates to a kind of shared experience that we all have. Because ultimately...you're looking for a connection, not a revelation about yourself."

One thing that certainly seems to connect us all these days is the news - no matter while side of the political aisle you fall on, it's hard to deny that current events are weighing heavily in our minds. With so much of our lives being affected by the current political climate, Black feels it would be disingenuous to not address it in his stand-up. However, he doesn't feel it's his job to try to change minds. "I think what I can do is make people feel like they're not crazy. To get on a stage and say, 'Hey this is all bananas. And if you feel like it's bananas, you're right. It's bananas.,' and try to do that with as much levity as I possibly can."

How will he do that this weekend? You'll just have to come and see, he says.

Michael Ian Black closes out the Milwaukee Comedy FestivalSunday night at Turner Hall Ballroom, Sunday night at 8.

Rachel is WUWM's Morning Edition host. <br/><br/>