3S. Illinois Gov. JB Pritzker Joins Jimmy Kimmel’s “ShowMeYourHellhole” Challenge — Bulletproof Vest and All
Illinois Governor JB Pritzker isn’t known for subtlety — in politics or in comedy. But his latest appearance on national television might be his most on-the-nose yet.
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On Thursday night’s Jimmy Kimmel Live!, the governor appeared in full mock-journalist mode, complete with a bulletproof vest and a faux-news tone, to join Kimmel’s new social media campaign, #ShowMeYourHellhole — a tongue-in-cheek response to President Donald Trump’s repeated claims that cities like Chicago and Portland are “hellholes.”
Standing on a downtown Chicago bridge with the skyline glowing behind him, Pritzker deadpanned into the camera:
“This is JB Pritzker, reporting from war-torn Chicago. As you can see, there’s utter mayhem and chaos on the ground. It’s quite disturbing. The Milwaukee Brewers have come in to attack our Chicago Cubs.”
What followed was a master class in self-aware satire — part sketch comedy, part political statement, and entirely Pritzker.
A “War-Torn” Chicago, as Imagined by Late Night
The bit, filmed earlier Thursday, continued with the governor cataloging Chicago’s “horrors”: hot dogs sullied with ketchup, deep-dish pizza gone shallow, and the ever-looming threat of losing to Milwaukee.
“I’m wearing body armor,” he added, gesturing toward his vest, “because you never know when a Cubs fan might throw a Vienna Beef.”
He closed with a grin:
“It’s a challenge to survive here in the city of Chicago, but there’s no hellscape that I’d rather be in.”
The sketch drew laughter from Kimmel’s studio audience and applause online, where the governor’s self-deprecating humor played well. Within hours, clips from the episode were circulating across X (formerly Twitter), Instagram, and YouTube, amassing millions of views.
Even the Wu-Tang Is for the Children fan account — a fixture of viral political memes — reposted the video, joking that “Pritzker just out-comedied half of late night.”
The Origins of the Challenge
Kimmel launched the #ShowMeYourHellhole challenge Wednesday night, inviting viewers in cities maligned by Trump to post videos showcasing how peaceful and vibrant their communities really are.
The campaign was a pointed response to the president’s second-term rhetoric, which has increasingly targeted Democratic-led urban centers as symbols of lawlessness. Since returning to office in January, Trump has deployed or proposed deploying federalized National Guard troops to 11 such cities — including Portland, Detroit, and Chicago.
“Apparently,” Kimmel said during his monologue, “we’re all living in post-apocalyptic war zones now. So if you happen to survive the chaos, maybe take a video — show us your local hellhole.”
Within 24 hours, hundreds of submissions had poured in. Viewers filmed kids playing soccer in Portland parks, tourists taking selfies in downtown Philadelphia, and restaurant patios buzzing in Minneapolis. Kimmel aired several of these clips Thursday night alongside Pritzker’s, dubbing the montage “America’s most adorable hellholes.”
Political Satire Meets Real-World Drama
Pritzker’s participation carried particular resonance, coming just hours after serious political developments in Chicago.
That same day, federal proceedings were underway at the Dirksen Federal Courthouse, where Illinois and the city of Chicago were suing to block Trump’s order to deploy the National Guard to the state.
By evening, U.S. District Judge April Perry had temporarily halted the order for two weeks — a short-term win for state officials, including Pritzker, who have argued that federal intervention in local law enforcement violates state sovereignty.
The governor, filming the sketch between court updates, seemed acutely aware of the tension. According to a Chicago Sun-Times report, several onlookers gathered during the shoot, including a former Illinois National Guard member.
“Well, I’m glad you’re not getting deployed now,” Pritzker quipped. The man responded dryly: “Yeah. Here or anywhere.”
The exchange perfectly captured the surreal blend of humor and gravity that defined both the day and the segment.
Kimmel’s Late-Night Provocation
For Kimmel, the challenge was vintage political satire — part catharsis, part defiance.
Since returning from suspension last month, the ABC host has doubled down on topical comedy, frequently mocking Trump’s second-term policies and the administration’s confrontations with blue-state governors.
Launching #ShowMeYourHellhole allowed Kimmel to enlist everyday Americans — and, apparently, governors — in pushing back against what he’s described as “fear-mongering dressed up as patriotism.”
“I love when politicians join in,” Kimmel said after airing Pritzker’s video. “It’s nice to see someone who can take a joke — and make one.”
The Humor Strategy
Pritzker’s appearance wasn’t his first foray into late-night comedy this year. He’s already logged two major cameos: a May interview on Jimmy Kimmel Live! following a speech in New Hampshire that sparked 2028 presidential chatter, and an August sit-down with Stephen Colbert.
But Thursday’s sketch marked a different tone — more Daily Show than Meet the Press.
It played directly into a recent trend of politicians using humor as soft power. In an era where social media blurs the line between politics and entertainment, viral comedy has become an increasingly valuable political tool.
“Humor allows politicians to appear approachable,” said media analyst Laurie Starke, “but it also lets them take control of the narrative. Pritzker wasn’t just joking about Trump’s language — he was reframing it.”
Indeed, while the #ShowMeYourHellhole clip mocked the president’s hyperbole, it also served as a visual rebuttal: Chicago, seen in all its late-summer beauty, looked calm, modern, and defiantly normal.
The Political Calculus
Pritzker, who has cultivated a national profile as one of the Democratic Party’s more media-savvy governors, seems to understand the optics.
His appearance Thursday wasn’t technically campaign-related — his team described it as “a friendly collaboration” with Kimmel’s staff — but it couldn’t have come at a more symbolic moment.
The lawsuit against Trump’s deployment order has elevated Pritzker’s standing among progressive voters while simultaneously making him a lightning rod for conservative critics.
“Going on late-night TV dressed in body armor to mock Trump might sound risky,” said University of Illinois political scientist Chris Mooney, “but for Pritzker’s audience, it plays as boldness. He’s owning the joke rather than being the punchline.”
Late-Night Governors: A Growing Trend
Pritzker’s appearance continues a pattern of governors — particularly from Democratic strongholds — embracing late-night as a platform to humanize their politics.
California’s Gavin Newsom has been a regular guest on The Late Show and The Daily Show, using humor to counter political attacks. Michigan’s Gretchen Whitmer went viral last year for parodying SNL’s “Weekend Update.”
The formula is simple: meet voters where they laugh.
“People don’t just watch debates anymore,” said Starke. “They watch monologues, podcasts, and sketches. That’s where opinions are formed.”
Chicago: The Real Hellhole?
Of course, not everyone was amused. Conservative pundits on social media called the segment “tone-deaf,” accusing Pritzker and Kimmel of trivializing real issues of crime and safety in Chicago.
Supporters countered that satire doesn’t deny problems — it punctures political exaggeration. As one viral reply put it, “If Chicago’s a hellhole, it’s the prettiest one I’ve ever seen.”
Meanwhile, Kimmel’s audience seemed to embrace the bit as both comedy and commentary. The clip has already surpassed five million views on YouTube, with thousands of comments praising the governor’s comedic timing.
The Broader Message
At its core, #ShowMeYourHellhole is a reminder of how late-night television still shapes national conversation — even in the age of streaming and short-form content.
By blending humor with political defiance, Kimmel has turned a soundbite (“hellhole”) into a rallying cry for civic pride. And by joining in, Pritzker turned himself into a symbol of that defiance — an elected official willing to poke fun at himself while standing up for his city.
“Comedy has always been part of Chicago’s DNA,” Pritzker said after the taping. “If we can’t laugh at ourselves, we’re in trouble.”
Closing Thoughts
In less than a minute of airtime, JB Pritzker managed to do what few politicians achieve: defend his city, lampoon his critics, and generate millions of laughs — all without breaking character.
For Jimmy Kimmel, it was proof that his brand of satire still has pull beyond Hollywood. For Pritzker, it was a masterclass in using humor to humanize politics.
And for viewers? It was a welcome reminder that sometimes, the best way to fight a “hellhole” narrative is with a hot dog, a smile, and a perfectly timed punchline.
Because if Chicago really is a war zone, it’s one where the jokes are still landing — and the governor’s wearing the body armor to prove it.
