The 12th annual Milwaukee Comedy Festival was the yearly event’s largest and largest-scale iteration to date. Not even including our semi-affiliated Roast Of Milwaukee, the Comedy Fest consisted of a whopping 12 shows taking place at five locations over the course of six days and nights. Before the weekend was through, frequent Bill Burr opener Nate Craig performed at 88Nine, a Lakefront Brewery showcase sold out, droves of comedy fans came to the basement of the Grand Avenue to take a number of shows at The Underground Collaborative, and longtime MadTV cast member Debra Wilson anchored an entertaining Shank Hall event.

The best and best-attended Milwaukee Comedy Festival ended in particularly strong and impressive fashion, as Michael Ian Black brought the festivities home Sunday night. In about 70 minutes, the actor, author, and comedian—just days removed from the release of Wet Hot American Summer: 10 Years Later, in which he played McKinley and a certain former U.S. president—delighted Turner Hall with a largely off-book set that found the humorist sampling cheese curds for the first time, debating the merits of fruit, taking the piss out of politicians, and sending festival-goers home smiling.

Before Black did his thing, Milwaukee’s own David Louis started the show off right with a short-but-sweet performance that was rife in tales of small town life, decorative pig thievery, and his inventive Yelp reviews. Louis gave way to John Egan, a Green Bay-based comic that bestowed about 20 minutes of self-effacing and side-splitting anecdotes of marriage, fatherhood, and the benefits of losing his virginity at age 21 upon the receptive crowd. Once Black was introduced, the headliner beckoned both Louis and Egan back to the stage to form a line of gray shirt and jeans-donning comedians. “Clearly, at least subconsciously, we’re all trying to convey something,” Black deadpanned. “And for me, it’s ‘lower your expectations.'”

After sending his openers backstage, the man of the hour took local pandering to new (and admittedly, quite inventive) levels by taking out a bag of cheese curds and allowing Milwaukee to watch him sample a regionally renowned nugget of dairy for the first time. On sight, he compared the hand-selected morsel of Henning’s Cajun Cheese Curd to a butt plug and reluctantly took a bite. “That’s not good,” he said, before calling an audience member (local comedian Jessie Kanter) to the stage for a futile attempt to coax a patented “squeak” from a piece of fresh cheese she picked. Meanwhile, Black placed his unfinished curd on a nearby monitor, saying “That’s how little I want it.”

While the curd-bashing and subsequent “morbid obesity” word association he’d derived from the Wisconsin dining staple risked forcing Black to work out of a hole before even starting his actual material, but the ballroom packed with tables of people seemed to appreciate the first set departure (of what turned out to be many) and ate up the state-specific insults as if they came with a side of ranch dressing. The lengthy unplanned opening bit eventually gave way to jokes about the sad state of the world and its association with the tiny house movement.

Partway through a Subway story that turned out to be an allegory to Trump’s ascension to the White House, Black stopped to remark about being distracted by an LCD screen at the back of the ballroom that was showing “comedians who are more successful than [him]” and then proceeded to let it cycle, commenting on each artist’s career in the process. After he explained why Martin Short, Trailer Park Boys, Demetri Martin, Mike Birbiglia, and John Cleese were superior to him, he seamlessly returned to his place in the Subway story, which elicited a massive applause. “Oh, you think I forgot where I was? I’m a successful comedian!” Black said. “I’m no Mike Birbiglia, but I’m successful nonetheless.”

The Subway sandwich story slowly crept on until Black received some unsolicited audience input as to why Black’s sandwich artist left jalapenos off his order when he’d clearly asked for every vegetable except cucumbers. A man yelling “jalapenos are a fruit!” stopped Black dead in his tracks. “Here’s the honest to God truth…I didn’t know that,” he said, which led to Black spending approximately 10 minutes asking for input on certain foods’ status as fruits, vegetables, gourds, and nuts. “So is a watermelon a gourd? Yes? FUCK! WHAT THE FUCK IS HAPPENING!”

Eventually, he finished the Subway story. “To be honest, I don’t have any material,” Black perhaps halfheartedly admitted, though he finished with a solid 20-minutes of anecdotes harvested from his latest special and one of his books. While much of his set was unscripted and, yes, minutes of contracted performance time were eaten through mid-material deviations about the venue, local dairy delicacies, and audience input, the vast majority of Black’s set was well-received and the informality seemed to perfectly tie into the week-long festival activities as a whole. Through this approach, Milwaukee Comedy Festival’s headliner wasn’t simply a nationally-noted comic doing his normal set verbatim. Whether or not it was intentional, Michael Ian Black mixed his decades of comedic credibility and his localized “had to be there” takes on Wisconsin and Turner Hall to put a brilliant bow on the latest and the best Milwaukee Comedy Festival yet.

About The Author

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Co-Founder and Editor

Before co-founding Milwaukee Record, Tyler Maas wrote for virtually every Milwaukee publication (except Wassup! Magazine). He lives in Bay View and enjoys both stuff and things.