Rod Blagojevich, Ryan Dempster and Triumph the Insult Comic Dog Walk Into a Bar: Reviewing a Strange Night in Chicago Comedy

Triumph the Insult Comic Dog hosted a “Jeopardy!”-style game show at the Den Theatre on June 3, 2024. (Marc Vitali / WTTW News)Triumph the Insult Comic Dog hosted a “Jeopardy!”-style game show at the Den Theatre on June 3, 2024. (Marc Vitali / WTTW News)

The former governor is a current glutton for punishment.

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What would inspire Rod Blagojevich to accept an invitation from a puppet dog with a penchant for profanity? Is it a need for attention? The desire to prove he can take it as well as give it? To show he’s a good sport?

None of these questions was answered Monday night at the Den Theatre in Wicker Park, where Triumph the Insult Comic Dog (aka comedian Robert Smigel) hosted a “Jeopardy!”-style game show with celebrity contestants, including ex-Cubs pitcher Ryan Dempster, actor Samm Levine and, of course, Blagojevich, who in 2010 was convicted on corruption charges after he attempted to sell the U.S. Senate seat vacated by then President-elect Barack Obama.

Light applause and loud boos welcomed Blagojevich to the sold-out theater. The former governor revealed that emcee Paul Konrad had warned him Triumph might play rough, and Blagojevich seemed guarded throughout the evening.

The puppet began by asking him about prison: “How long were you in there?” “Eight years,” Blagojevich said. Triumph poked his head toward the crowd and said, almost sympathetically, “He’s an ---hole, but come on!”

The host then needled Blagojevich about his support of former President Donald Trump, who last week became the first former U.S. president to be convicted of felony crimes.

“You get me out of prison, you’ve got my vote,” Blagojevich said proudly. Or shamelessly, depending on your point of view.

At the mention of Trump, the crowd jeered.

“Oh, come on,” said Triumph, reprimanding the crowd as if stating the obvious. “We know. We all know. Anybody with a brain knows that.”

Triumph told Blagojevich that Trump likes the ex-governor because “just like him, you show no remorse and no forehead.” And the rowdy Rottweiler gave Blagojevich a prison-related tip: “You should give Trump your recipe for toilet wine.”

“I’m a Trumpocrat,” Blagojevich said to groans and boos.

“Is that like a Transervative?” Triumph responded.

Triumph pushed the onetime public servant and advocate for reproductive rights on his support for Trump, who last year bragged “I was able to kill Roe v. Wade.”

Blagojevich, a former contestant on “Celebrity Apprentice,” said it again: “You get me out of prison, you’ve got my vote.”

“Public shmublic!” howled Triumph. “Abortion ashmortion!”

Oblivious to any appearance of conflict, Blagojevich boasted about his record of supporting women and children and everyone else. He even brought up “free bus rides for seniors.” He’s still proud of that one.

The game began. It was called “Let’s Make a Poop.”

Each contestant was given a buzzer with a specific sound effect: Dempster’s was Harry Caray saying,“Where am I?” Blagojevich had Trump saying “Hannibal Lecter!” Perhaps that was what made Blagojevich hesitant to hit the buzzer and play the game, but more likely it was an effort to stay out of Triumph’s crosshairs.

At times the former governor cussed like a salty sailor. He mentioned going through two boxes of crayons while working on his memoir, and that earned him his biggest laugh of the night. If you’re keeping track, he’s also dyeing his hair again.

There were special guests, including Poochie, the woman who had a famous confrontation with Triumph at Wiener’s Circle in 2012. A supervisor from the Department of Streets and Sanitation was introduced to big applause — until it was announced he was responsible for paving over the “rat hole” in Roscoe Village. Then he was booed like Blago.

There were jokes about Kanye West: “He’s such a Renaissance Man, so busy, and yet still he finds time to hate the Jews.” There were rim shots from a drum kit and cracks about prison sex, violent crime and the value of a degree from Triton.

One clue in the game was: “This loud and incessant noise is louder than cicadas.” The answer: “What is the press talking about cicadas?”

There was more Trump bashing to the partisan crowd — “He now slurs his slurs” — and a crude bit about Trump accusing Judge Juan Merchan of breaking wind in court and blaming Trump. “He ventrili-farts.”

The evening began with Smigel playing Carl of the Superfans (“da Bears”) along with some fill-in Superfans. These days the Superfans cling to the belief that Chicago sports teams are actually doing great in other parts of the multiverse. They sang “All About That Bass” as “All About the Bears,” and “Edelweiss” became “Eberflus.”

It was a silly, fun and inexplicable evening as the onetime governor looked like a fish in a barrel, eyeing the fisherman and wondering how he got into this predicament. He wasn’t alone.

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