Chicago Bob

Chicago’s skyline is so iconic they named their WNBA team the Sky… but the city takes the “skyscraper” obsession to a whole new level Meet the Metropolitan Correctional Center — Chicago’s 28-story federal prison that’s literally a brutalist skyscraper right downtown on Van Buren Street. 😆🏙️
Designed in the 1970s by famed architect Harry Weese as a “humane” modern jail, it featured slit windows (no bars!), rooftop recreation yards with skyline views, a gym, library, and even board games.
Yet it still housed some notorious inmates like El Chapo, Rod Blagojevich, and R. Kelly. And yes… people still tried to escape using dental floss ropes and tied-up bedsheets 😭
Only in Chicago would you find a prison with better views than most luxury condos.
This building is equal parts fascinating and wildly creepy.
Like 👍 if you find this skyscraper prison insane, and drop a comment below: Would you rather be in a regular prison or this one with a view? 👇
Follow for more wild Chicago history and architecture stories!

Metropolitan Correctional Center: Where El Chapo & R. Kelly Had Skyline Views (And Tried to Escape!) Chicago's skyline is iconic—so much so that even its women's basketball team is called the Sky. But the city takes "skyscraper everything" to extremes: from ...

My grandpa was a Wisconsin dairy farmer who thought it was hilarious to grab an electric fence and then shake his grandsons’ hands That was “tough” back then. No seatbelts. Falling out of moving cars and still going to school the next day. Snow days required three feet of snow and negative 100 degree temperatures. Folks were just built different. And in 1850 Chicago, they needed that kind of toughness bad. Crime was everywhere — so a 31-year-old Scottish barrel maker named Allan Pinkerton opened America’s very first private detective agency right here in the city. This is the wild true story of the Pinkerton National Detective Agency — the original hard-boiled private eyes. They protected Abraham Lincoln, hired the first female detective in the U.S., busted counterfeiting rings, and got pulled into some of the most violent labor wars in American history. All from a tiny office at Washington and Dearborn… which is now a Target If you love Chicago history with a side of “people used to be insane,” this one’s for you. Like if your grandpa was built different, and drop a comment:
What’s the most “old school tough” thing your family used to do? Follow for more Chicago stories!

The Real Story of Pinkerton: Chicago’s Original Hardass Private Detectives My grandpa was a Wisconsin dairy farmer who thought it was hilarious to grab an electric fence and then shake his grandsons’ hands 😆 ⚡️That was “tough” back...

When you’re just trying to get to work on the Red Line at 8am and Chicago does what Chicago does 😆💩
Monkey said: I ain’t seen nothin’
Real ones know the code.

“🚀 First Chicago Bob Comical History Tour of 2026 is in the books!
Ended at The Bean with my favorite crew — big smiles, zero boring facts, and the best distorted skyline in Chicago 😂
Comical history + real Chicago vibes = the perfect way to kick off the seasons.
Who’s joining the next tour? Drop a 🔥 below if you’re in!
ChicagoThingsToDo ChicagoBob VisitChicago”

Shrog spots the bust by the river and asks: “Who is this statue, Bob?” 🤔
Meet Jean Baptiste Point du Sable — recognized as Chicago’s first permanent non-Native settler and the true founder of the city.
A freed man of Haitian descent, he arrived in the late 1700s as a fur trader and built the original trading post right at the mouth of the Chicago River — the exact spot that’s now prime real estate on the Magnificent Mile. His legacy helped shape the Chicago we know today.
The bust at Pioneer Court is a quiet but powerful reminder of the city’s origins. Shrog has some thoughts on how dramatically that area has changed over the years… and Chicago history has a way of responding! 😆
Next time you’re crossing the DuSable Bridge, take a moment to check it out.
If you enjoy Chicago history, hidden gems, and Shrog’s hilarious takes, like this video and follow the page for more!

DuSable Statue: Chicago's Founder & the Apple Store Twist! Shrog spots the bust by the river: "Who is this statue, Bob?"It's Jean Baptiste Point du Sable—recognized as Chicago's first permanent non-Native settler and...

Peter Jackson’s new LOTR co-writer: Stephen Colbert
“The ultimate Tolkien superfan!”
GOOD DAY, SIR! 😆
The books fans are in shambles.
You team Colbert or team meltdown?

Chicagoans are “nice”… until you ask for directions and suddenly the whole block turns into a debate club 😆
Back before GPS saved (or ruined) everything, Chicago had the Chicago Motor Club — the 1907 crew of wealthy auto enthusiasts who literally fixed Illinois’ muddy roads, lobbied hard for Route 66, built that gorgeous Art Deco headquarters on Wacker Drive, handed out real paper maps, and actually came to help when you broke down.
In this 3:51 snarky video I dig into how the CMC started, boomed, survived the Depression with pure “See America First” energy… and where it all ended up.
Real Chicago history, zero gloss.
Drop your worst “Chicago directions” horror story in the comments 👇
(We’ve all been there.)
👍 Like if you miss (or dread) asking locals
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Chicago Motor Club: Before GPS Ruined Directions Chicagoans are "nice"... until you ask for directions and watch the debate club erupt. Back before GPS saved (or ruined) everything, there was the Chicago Mo...

😂 Same face, different nightmares.
Top: Cubs give up a grand slam
Bottom: Cubs hit a grand slam
Craig Counsell staying forever unimpressed. Classic. ⚾
Who else lives for these deadpan manager reactions? Drop your favorite below 👇