Chicagoans Reveal Their Best (and Worst) Celebrity Encounters — And Wow, Some of These Are WILD

From Jerry Springer’s limo to R. Kelly’s Navy Pier meltdown, locals are spilling the tea on celebrity encounters.

Chicago isn’t LA or New York. No paparazzi at every Starbucks. No velvet ropes at the grocery store.

But we’ve got something better: real, unfiltered encounters between regular Chicagoans and famous people who thought they could just… blend in.

Spoiler: some can. Some really, really can’t.

A Reddit thread asked locals for their best and worst celebrity stories, and the responses are legendary. Comedy icons, athletes acting like jerks, total chaos.

Let’s count down the most memorable, from mildly interesting to absolutely insane.

#12: Michael Shannon — The Perpetual Old Town Ale House Patron

Here’s the thing about Michael Shannon:

The man is everywhere in Chicago, and he just wants to be left alone.

Multiple Redditors reported running into him at Old Town Ale House (his apparent second home), and the consensus is mixed. One person got snapped at in Trader Joe’s when they complimented his work on Boardwalk Empire. His response? Just “thanks” and a visible eye roll.

But hold up—

Others who approached him more casually had completely different experiences. One person met him multiple times, got photos, and found him “super cool.” Another caught him at the Empty Bottle and said he was friendly.

The pattern? If you treat Michael Shannon like a regular dude having a beer, he’ll be cool. If you fanboy at him while he’s buying groceries, you’re gonna get the death stare.

Fair enough, honestly.

#11: John Cusack — Jekyll and Hyde of the North Side

Oh boy, where do we even start with this one?

John Cusack might be the most polarizing celebrity in Chicago. The stories about him are all over the map.

One person had a pleasant chat with him at club seats during a Cubs game and didn’t even realize it was him until later. Another saw him vaping inside The Loyalist—where he’s apparently a partner—blowing “fat clouds” and doing whatever he wants.

But then there’s the dark side:

Multiple people report Cusack being an absolute dick. One server said their husband waited on him and “still talks about how awful he was.” Someone else watched him hit on a woman at a game, get rejected, and then leave in the 6th inning looking furious. Another person filming High Fidelity at Lane Tech said he “was a jackass.”

The most telling detail? His sister Joan gets universally praised as lovely and down-to-earth, while John gets roasted in nearly every story.

Time to address the elephant in the room:

#10: Jeremy Piven — Universally Hated

We need to talk about Jeremy Piven because the man has achieved something remarkable:

Literally not one single person had a positive Jeremy Piven story.

Not one.

A server at a high-end restaurant said he tipped his LA waitress with a DVD of Entourage after running up a huge bill. Someone who worked at a clothing store in LA said he “berated everyone” and “acted like an entitled douche.”

Another person who worked in the West Loop said he was a “grade A asshole.” Someone else got shoulder-checked by him at Taste of Chicago, and when they apologized, Piven snapped: “watch where you’re fuckin goin.”

The phrase “if you know, you know” kept appearing in the comments whenever his name came up.

Consider this your warning if you ever spot The Piv in the wild.

#9: Vince Vaughn — The Height King Who’s Actually Cool

Here’s a fun pattern:

Everyone mentions how tall Vince Vaughn is, and then they mention how surprisingly nice he was.

Multiple people ran into him at bars, Hawks games, and around town. One person met him on the lakefront path during his peak (“Old School,” “The Break-Up” era) and said he was “super nice” and stopped to chat.

Another met him at a Cubs game before it started, played paper finger football with Robbie Gould, and Vaughn was right there being hilarious.

But here’s the flip side—one restaurant worker said Vaughn was “one of the biggest assholes” they ever met, “complaining like a bitch about other customers recognizing him.”

So maybe the lesson is: catch Vince Vaughn when he’s out having fun, not when he’s trying to eat in peace?

#8: A Quick Break for the Good Guys

Let’s take a quick break for some feel-good moments because not everyone in this city is a disaster:

Walter Payton pulled over on I-90 and changed a tire for a young driver. Just stopped his car, got out, and helped a stranger. The same person also met Tom Hanks (genuine and funny) and said Sweetness was the most memorable—because of course he was.

Danny Pudi from “Community” showed up at an iO Theater improv show, sat at a table with a couple on a date, chatted like normal people, and then bought their drinks without them knowing until after he left. The couple is still together years later and credits that magical night.

Patrick Sharp handed out candy every Halloween in Lakeview. Theo Epstein stopped on the street the day after the Cubs won the World Series—exhausted, probably hungover—and took pictures with kids anyway.

Tom Skilling hugged a fan who said they missed him and talked for a while after he retired.

These are the stories that remind you why Chicago’s different.

But let’s get back to the chaos:

#7: Scottie Pippen — The Most Inconsistent Legend

Scottie Pippen stories are absolutely baffling because they’re completely contradictory.

One side: Someone saw him at a rec league basketball game supporting his son and said he was “one of the most down to earth people” and “very kind.” Another person got a polite interaction at Ikea in Schaumburg.

The other side: Multiple servers said he didn’t tip. One server was told “your tip is you get to tell people you waited on Scottie Pippen.” Another person said he used to walk his dogs in the alley and never picked up the shit. Someone else said he just ignored them when they said hello at an airline counter.

One person saw him cut them off illegally on I-90 in a massive Jeep Wrangler and flipped him off when they caught up to him.

So which is it, Scottie?

#6: Jerry Springer — The Limo Legend

This one’s amazing:

Jerry Springer dropped three random guys off at a bar in his limo.

That’s it. That’s the story. But multiple people confirmed similar experiences—apparently Jerry used to pick up law students around Loyola and take them for drinks at Pippins. One person said they got in his limo and went to his show, which was “fun and crazy.”

Another person saw him at Dixie Kitchen in Evanston but couldn’t get seated because they were about to close. Jerry and his wife understood and were gracious about it.

The man filmed his show in Chicago for years and apparently just vibed around the city being inexplicably generous and cool.

RIP to a real one.

#5: Chance the Rapper — Everywhere, All the Time, Always Nice

Before COVID, you couldn’t go anywhere in Chicago without running into Chance.

One person saw him literally everywhere during NBA All-Star weekend. Someone else hung out with him at a dive bar after realizing the “poor punk artist dude” they’d been giving free drinks to was actually making Chance’s music videos.

Multiple people mentioned he was consistently nice, humble, and willing to chat. One person met him at an event and he took time for everyone. Another saw him at a coffee shop with his daughter and said he was friendly with the staff.

One random detail: Someone saw him try to walk out on a bill at Soho House—but apparently he just thought someone else in his huge group had paid, and he settled it immediately when the server stopped him.

The man really is just out here living his Chicago life.

#4: Bill Murray — The Patron Saint of Chicago

We can’t have a celebrity encounter article without Bill Murray.

One person bummed a cigarette from Mark Grace at Gibson’s, but the real story is Bill Murray at Earwax—just eating lunch, giving the mutual head nod of respect, and going about his day.

Another person watched Bill at a theater and said he was “admirable in how he responded to fans.”

Here’s my favorite: In the ’90s, a radio deejay tested Chicago’s friendliness by having someone hail cabs, claim they lost their wallet, and ask for a free ride to the police station. Out of three cabs, only one refused. The city passed the test.

But the real test? Bill Murray exists in this city and we collectively leave him alone unless he engages first.

That’s the code.

#3: R. Kelly — The Navy Pier Nightmare (And Other Horror Stories)

Alright, buckle up because this is dark:

R. Kelly had a full meltdown at Navy Pier because he couldn’t fit his entire entourage on the Ferris wheel.

A manager working the photo area watched him “absolutely fucking lose it”—kicking stanchions, knocking over queue scenery, trampling landscaping—because someone told him “no” for the first time in years. This was around 20 years ago, and apparently it was “the first time he’d heard ‘no’ in a long time.”

Multiple studio engineers from that era said they were told to “lock the door and walk away if he showed up.”

Someone else went to a house party at his Olympia Fields mansion (they had to wear all black, park at a Holiday Inn, and take a limo to the house). The party included a private concert, sit-down dinner, and cardboard cutouts of R. Kelly everywhere. The kicker? “The whole reason behind this party? His good friend was going away for 4 years to jail. We all wore black for him.”

Years later during his trial, someone saw him working out at XSport in Old Town. “I assume he went there because it was cheap, he was now broke and the people there would likely not recognize him.”

Absolutely unhinged. All of it.

#2: Chris Farley — The Late-Night Legend Who Made Time for Fans

This one will make you emotional:

In 1995, someone went to Second City’s free late show with a friend. Chris Farley’s brother John was performing, and Chris showed up mid-show, jumped in, fell through a coffee table, and was “intense and wild.”

After the show, the brothers came outside and Chris said to two young fans: “Hey, I’m Chris. This is my brother John. Were you guys at the show? We’re going to the bar across the street. You wanna come hang out?”

The fans were underage and declined (kicking themselves later for not just going anyway), but Chris chatted with them for a few minutes before heading to the bar.

“Such a friendly guy,” they wrote.

This was probably less than two years before he died. He was still out here being genuinely kind to random people on the street.

Man.

#1: The Ultimate Chicago Celebrity Truth — It’s a Two-Way Street

Here’s what we learned from 700+ comments:

Chicago celebrities get treated the way they treat Chicago.

Michael Shannon gets left alone at Old Town Ale House because he’s been respectfully drinking there for years. Bill Murray gets the head nod because he’s never acted like he’s above anyone. Vince Vaughn can walk around because he’s generally cool to people (height mentions aside).

But Jeremy Piven? John Cusack? Scottie Pippen with his no-tip bullshit?

They get roasted in Reddit threads forever.

The beautiful thing about Chicago is we have that Midwest nice… until you give us a reason not to. We’ll hold the door for you. We’ll give you directions. We’ll pretend we didn’t recognize you at the grocery store.

But the second you act like an entitled prick? The whole city will remember.

That’s the code. That’s always been the code.

And honestly? That’s exactly how it should be.

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So what’s YOUR celebrity encounter story? See someone famous at the Jewel? Get snubbed by an athlete at a restaurant? Tell us in the comments — we want to hear it all.