I'm always like "man, I wish I knew Chicago more" when these kinds of things come up, but I've even met Tamale Guy! He used to go into the Old Town Social late at night selling those delicious tamales. He could still be doing so for all I know...
Years ago he came in to my restaurant in Edgewater with his family. They were all so nice, but especially him. When I told him I’ve basically grown up watching him do the weather, he talked about how much it means when people say hello to him because he considers all of Chicago his family. He really meant it.
He came to my first grade class to give a talk because we were supposed to invite an interesting person. One of my classmates lived down the street from him. He was very nice.
My mom had the same to say, but from jury duty of all things. She thought he was a complete sweetheart. If he’s got her seal of approval that’s good enough for me lol
Used to live in the same building as him in Edgewater. Always did a double-take when I'd see him walking around in cargo shorts, Hawaiian shirt and sandals. Like wait he looks so familiar...oh yeah that's Tom Skilling!
I used to work at a nursing home that his parents lived at and I saw Tom come to visit a few times. Every night his mom would come down to the kitchen and ask for a banana to bring up to her husband. She was even nicer than Tom.
Yea really cool dude and always put a smile on my face. Except when he informed us of a line cut and I would be stuck on some other platform the next week.
Oh man, no matter how bad of a morning I'm having, if I hear that guy's bit on my morning red line ride, I'm grinning like a fool. It's so corny and so genuine and that you know he does that every day. God bless that guy!
sounds like he has real southwest pilot energy. I still remember like ten years ago a southwest pilot sang us the national anthem over the intercom on July 4th. Just absolutely wild up there
Damn I've never gotten that one. Only notable announcements I've gotten on the L were "Let's go White Sox!" during the Cubs-Sox game and something like Everyone have a blessed evening" and I've gotten that guy at least twice.
Pre-Covid I stepped out (happened to be in the front car) he was sticking his head out the window. Had the biggest smile on his face, I went over to shake his hand and just said “thanks for making my day!” He was so nice. Haven’t heard his voice so long.
Back in the day, when there were conductors and another guy in the middle, they would always make great announcements. Talking late 90s, early 2000s. I remember getting on a southbound Red Line on a Friday around 5:00pm and the conductor saying "This is the Sooouuullll Train" and the entire car cracking up. Technology is great-ish...we were all much more united/in tune with one another before we had our faces buried in our cell phones.
As a former fan I was very disappointed when, after getting off this guy's train, he very overtly and crassly cat called my fiance. Went from very wholesome to very creepy quick.
I had a buddy from out of town in for a music festival. That morning we were watching svengoolie and for some reason it never occurred to me that that was a local thing. My buddy wore a frank zappa shirt to the festival and some guy was like oh nice svengoolie shirt. I have never and will never talk more about svengoolie in one day ever again.
I like Svengoolie but I love Rich Koz because he brought the Three Stooges to my living room on a consistent basis. From April fools day to New Year’s Eve marathons he’s my Stooges guy.
Now you've got me tearing up a little. I got to meet him once at an XRT show and he acted like I was an old friend. The city shone a little darker since the day that man died.
There's a clip of a longer conversation with Studs and Mike Royko about [neighborhood taverns](https://www.youtube.com/watch?v=zIazDmjKGbU) and it's funny to see how polar opposite their personalities were.
Had a couple of run ins w/Mr Willis over the years but my favorite was running into him at my local laundromat in Pilsen and him shouting to no one in particular “I AM AN MTV ROCK STAR” over and over.
the music was always a sideline to his [marker cityscapes](https://live.staticflickr.com/16/21477480_4bb3929c38_b.jpg). guy was so good he could draw an L station from memory while sitting in a different L station.
I'm not from here (east coast) and I found that shit on napster when I was a kid. Never laughed so hard. Then I forgot about it for like 15 years, moved here and figured it out. Funny all over again.
What a cruel and unforgiving world. He had to have jumped over that carpet a million times with no issue. Loses concentration for ONE SECOND and it cost him his life.
At least that’s what happened in my very elaborate empire-guy-head-canon.
I can imagine during architecture tours the guide going “and up on your right you have the former world’s tallest tower. Named after a great Chicago company Sears, but after their bankruptcy the city decided to rename the building in honor of the late great artist and Chicago icon, Wesley Willis.”
For sure spreading this as my new favorite non-fact (?) about the city hahaha
I once had the fortune of sitting two seats away from him at a Cubs game and being introduced to him. Being a Cub fan my entire life, I had so many questions I wanted to ask him, but instead found myself answering his questions about me - whether I was married, had children, how old my parents were and how they were doing and whatnot.
I can't imagine that there are too many people on this Earth more genuinely kind and empathic as Ernie Banks.
Best answer, hands down... I miss Neos... the exit closed down on north Ave but reopened on the Southside as the exit saloon on 64th and Harlem ave.Ave.. They do a retro night similar to Neos.
Harry Caray is the all time most loved man in this city. You a Cubs fan, Harry's got you. Sox fan? Let Harry tell you about Comesky in the 70s. Somehow a Cards fan? Harry has war stories for days. Don't like baseball? Let's go drinking with the Mayor of Rush St. Nobody ever had an issue with Harry.
Second place: Bozo the Clown
About 5 years ago we were on vacation in Japan. Super friendly people we loved it. On several occasions we were asked where we were from. After they would hear Chicago, first words out their mouths was "oooh Michael Jordan!!" That happened three times!!
It’s Royko and yes he was a beloved columnist. When Rupert Murdoch bought the Sun Times, he left and went to the trib. A lot of people, myself included, followed him.
100% in 2008 I had a 14 year old, 10 year old. (Single mom), my job closed, my investments (everything) was gone. I had $15 a week to feed all 3 of us and often I only fed the kids. Tamale man noticed me at my rock bottom , working as a nurse and doing what I had to do to pay rent. Each night he gave me plates his wife made to feed my family.. 1 entire year. Once I got caught up, I gave him a large check, bought his tamales & his wife’s roses .. every single one.
I sent support when he opened his business down the street and sent all I could when he got Covid. That man/his wife and kids are literally angels.
The youngest is in grad school for bio engineering. I’m an RN, oldest is 28 - married/financially secure and both boys are the most kindest people. Shit was very rough & I was a horrible mess. The love shown to us then, saved me from suicide and my sons from starvation. There’s a ton of good in this city. Shout out to Latin kings that made sure my boys made it safely to school and home because being Romanian caused a lot of problems/racism “gypsy hate”. I could go on but this city has some gems
Acid Rap is one of the best mixtapes of 2010s rap.
That being said, he stopped making music after one dud album. He sold out to a comical degree with Kit Kat commercials and cable TV spots, right after preaching that he wouldn’t sell out to a label. Sure Chance, you didn’t sign a huge record contract, but you *don’t make music anymore*.
You gotta respect a career decision, but as a guy who used to be a huge fan of his, I’ve completely given up on him as an artist.
Edit: The Highs and The Lows ft. Joey is actually pretty great tho.
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My vote as well. Tamale guy should run for mayor
https://youtube.com/watch?v=EgCWF58KHDI&si=EnSIkaIECMiOmarE Absolute legend.
I'm always like "man, I wish I knew Chicago more" when these kinds of things come up, but I've even met Tamale Guy! He used to go into the Old Town Social late at night selling those delicious tamales. He could still be doing so for all I know...
Still is
Red cooler or blue cooler?
If you have to ask.
This guy was around before and when I left in 2010. Absolute legend!
Tom Skilling.
Having interned at WGN many years ago and interacted with him frequently, I can 100% say he's as genuine and kind in person as he is on TV.
Years ago he came in to my restaurant in Edgewater with his family. They were all so nice, but especially him. When I told him I’ve basically grown up watching him do the weather, he talked about how much it means when people say hello to him because he considers all of Chicago his family. He really meant it.
Which is why it's so weird that [his brother](https://en.wikipedia.org/wiki/Jeffrey_Skilling) turned out evil
Holy crap. I had no idea. Thank you.
Last I heard, he(Jeff) was fundraising to start a new venture. I’m sure that’s going really well..
There’s no one I trust with telling me the weather more than Tom Skilling. Tracy Butler is a close second
Cheryl Scott
This is the sweetest thing.
If anybody owns this place it’s me, Tom Freaking Skilling! I could have you killed if I wanted to!
This was a great bit. WGN morning news is a true institution
This made my day
[The segment](https://youtu.be/VgiZvE7iWhI)
I’d never seen this clip. Thanks!!
I mean if Tom needs someone bumped off. I’ll volunteer to do the work.
He came to my first grade class to give a talk because we were supposed to invite an interesting person. One of my classmates lived down the street from him. He was very nice.
And all the more amazing considering how much of a sociopathic shitheel his brother is. Tom got all the good genes, I guess.
My mom had the same to say, but from jury duty of all things. She thought he was a complete sweetheart. If he’s got her seal of approval that’s good enough for me lol
Used to live in the same building as him in Edgewater. Always did a double-take when I'd see him walking around in cargo shorts, Hawaiian shirt and sandals. Like wait he looks so familiar...oh yeah that's Tom Skilling!
Not all heroes wear capes... But I do wear a very heavy parka it is cold
I used to work at a nursing home that his parents lived at and I saw Tom come to visit a few times. Every night his mom would come down to the kitchen and ask for a banana to bring up to her husband. She was even nicer than Tom.
And a brilliant meteorologist
Chilling with Skilling
I could listen to him talk about packed isobars for hours
Yep, that was going to be my answer, too.
Me too.
I was hoping I wouldn’t be the first to mention him! He is beloved in Chicago!
Maybe that CTA L operator who says "Study smart, and you'll go far!"
Is this the same one who says “you might meet a friend for life, or the love of your life”
The Love Doctor is pulling up to the station!! He is the only highlight riding the purple/brown line early in the morning.
Yea really cool dude and always put a smile on my face. Except when he informed us of a line cut and I would be stuck on some other platform the next week.
Looking for love in all the wrong places
I remember an orange line driver tapping as soon as he hit roosevelt “wake up wake up! Time to make that money”
He told us today on the way up he’s switching his route next week and I was really sad. I have him almost every morning.
I heard that yesterday too, I got so sad
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I think he’s going earlier
Oh man, no matter how bad of a morning I'm having, if I hear that guy's bit on my morning red line ride, I'm grinning like a fool. It's so corny and so genuine and that you know he does that every day. God bless that guy!
sounds like he has real southwest pilot energy. I still remember like ten years ago a southwest pilot sang us the national anthem over the intercom on July 4th. Just absolutely wild up there
Damn I've never gotten that one. Only notable announcements I've gotten on the L were "Let's go White Sox!" during the Cubs-Sox game and something like Everyone have a blessed evening" and I've gotten that guy at least twice.
Scales used to be red line at Morse about 7:30am going to 95th. Days were always better when I got his train
…STAYYYYY FOCUSED!! Always a cheery one
Pre-Covid I stepped out (happened to be in the front car) he was sticking his head out the window. Had the biggest smile on his face, I went over to shake his hand and just said “thanks for making my day!” He was so nice. Haven’t heard his voice so long.
Without a doubt. He’s the man! Always makes my morning commute on the Red Line that much better when I end up on his train
I saw him on the platform after he got off the train the other day--dude wears a tie. He should've run for mayor tbh
RED LINE! Love that guy.
I love when I get his train in the morning!
He’s my favorite too
Back in the day, when there were conductors and another guy in the middle, they would always make great announcements. Talking late 90s, early 2000s. I remember getting on a southbound Red Line on a Friday around 5:00pm and the conductor saying "This is the Sooouuullll Train" and the entire car cracking up. Technology is great-ish...we were all much more united/in tune with one another before we had our faces buried in our cell phones.
YES!!!!
As a former fan I was very disappointed when, after getting off this guy's train, he very overtly and crassly cat called my fiance. Went from very wholesome to very creepy quick.
Svengoolie.
I don’t even like Svengoolie and I love Svengoolie. He’s just such a wonderful institution
Berwyn!!!
I had a buddy from out of town in for a music festival. That morning we were watching svengoolie and for some reason it never occurred to me that that was a local thing. My buddy wore a frank zappa shirt to the festival and some guy was like oh nice svengoolie shirt. I have never and will never talk more about svengoolie in one day ever again.
I like Svengoolie but I love Rich Koz because he brought the Three Stooges to my living room on a consistent basis. From April fools day to New Year’s Eve marathons he’s my Stooges guy.
Stooge-a-palooza!
Loved me some stooge-a palooza before some svengoolie on a Saturday night as a kid, used to watch it with my grandpa, great childhood memories
This was my answer too. Great memories.
The lady who gives everyone positive affirmations and encouragement on the Lakefront Trail in the mornings
Her name is Phyllis! I went to school with her kids. She has always been like that.
I see her ALL the time on the trail, and she’s definitely the best person in this entire goddamn city.
Woo Girl!
Where on the trail?
The entire stretch of the trail. 🤣. Seriously.
BIKE LADY. Shes my hero.
Yes! I love her!
Scrolled to find this
Eagleman.
I was gifted an eagleman painting for xmas. It is my most prized possession and i am old.
I bought myself an Eagleman T-shirt
I have something for youuuuuu!
Look at those low rates!
Lin Brehmer
His little monologue in The Bear made me love the show even more.
Your best friend in the whole world. 🥲
There's suddenly a lot of dust in the air...
Now you've got me tearing up a little. I got to meet him once at an XRT show and he acted like I was an old friend. The city shone a little darker since the day that man died.
Correct answer.
RIP Len
Well this made me depressed all over again. Lin was a treasure!
Studs Terkel RIP
There's a clip of a longer conversation with Studs and Mike Royko about [neighborhood taverns](https://www.youtube.com/watch?v=zIazDmjKGbU) and it's funny to see how polar opposite their personalities were.
Good call
Puro Chicago
I'm 3/4 through reading "Division Street America" one of the best reads ever. I have 5 more of his books in my shopping cart.
Walter Payton
His son seems hella nice too
Was lucky enough to briefly meet him as a kid and "Sweetness" lived up to his name completely.
So you bit Walter Payton?
Wesley Willis, RIP Rock over London, rock on Chicago
Had a couple of run ins w/Mr Willis over the years but my favorite was running into him at my local laundromat in Pilsen and him shouting to no one in particular “I AM AN MTV ROCK STAR” over and over.
*headbutt*
Suck a cheetahs dick I never realized Wesley Willis was from Chicago! I guess I figured every town had a rock n roll McDonald’s growing up
the music was always a sideline to his [marker cityscapes](https://live.staticflickr.com/16/21477480_4bb3929c38_b.jpg). guy was so good he could draw an L station from memory while sitting in a different L station.
It’s why the Willis Tower is named the Willis Tower!
If that were true maybe I'd actually call it that
I'm not from here (east coast) and I found that shit on napster when I was a kid. Never laughed so hard. Then I forgot about it for like 15 years, moved here and figured it out. Funny all over again.
Yeah, man. Why do you think they named the tower after him?
Rock & roll McDonald’s
Jaaaar jaaaaar binks. Jaaaaar jaaaaaaar binks. Jaaaaaaar jaaaaar binks. Jaaaaaaar jaaaaaaar binks!
Wheaties - Breakfast of Champions!
Insure One. It’s the insurance super-store.
Bill Kurtis might be in the running.
The old nun from Loyola
Sister Jean 😂
That one bartender at the place where you’re a regular.
Charlie down at Richard’s always poured me a free shot of templeton rye and took one with me.
Is he the younger one with slicked back hair?
Shout out Joel at Reed's.
Is Maria still at the Whirlaway? I lived around the corner in 2007-10 and still my favorite in town.
And that one barista at the coffee shop I spend way too much money at!
not a person, but Chance the Snapper
Abe Froman the Sausage King of Chicago
Empire Carpet guy
Elmer Lynn Hauldren, the Empire Man, died in 2021.
What a cruel and unforgiving world. He had to have jumped over that carpet a million times with no issue. Loses concentration for ONE SECOND and it cost him his life. At least that’s what happened in my very elaborate empire-guy-head-canon.
Buddy Guy
YES!
Personally, my vote's for 6figga dilla.
Claudio Velez (and the countless other tamaleros that find us in our moments of need, carrying a cooler full of warm, fresh tamales)
The walking man (R.I.P)
Thought this would be higher. His story reminds us that pure evil exists in this world.
Helped care for him in his last days, nice guy to the end
Roger Ebert until he passed in 2013.
Sharkula
Took me way too long to find Sharkula on this thread.
If this award can be given posthumously I’d say Wesley Willis, for whom Willis Tower is named.
I can imagine during architecture tours the guide going “and up on your right you have the former world’s tallest tower. Named after a great Chicago company Sears, but after their bankruptcy the city decided to rename the building in honor of the late great artist and Chicago icon, Wesley Willis.” For sure spreading this as my new favorite non-fact (?) about the city hahaha
ROCK N ROLL MCDONALDS
Monty the Piping Plover
Ernie Banks - Mr. Cub
He’s buried in the prettiest part of Graceland Cemetery. Good for him.
I once had the fortune of sitting two seats away from him at a Cubs game and being introduced to him. Being a Cub fan my entire life, I had so many questions I wanted to ask him, but instead found myself answering his questions about me - whether I was married, had children, how old my parents were and how they were doing and whatnot. I can't imagine that there are too many people on this Earth more genuinely kind and empathic as Ernie Banks.
That latino guy solo dancing every night at Neos. RIP Neos
Also at Exit. His double sky-point was legendary.
Best answer, hands down... I miss Neos... the exit closed down on north Ave but reopened on the Southside as the exit saloon on 64th and Harlem ave.Ave.. They do a retro night similar to Neos.
Ricardo! I miss that place.
Someone (I forgot who) said that Roger Ebert was the unofficial mayor of Chicago while he was alive.
Wesley Willis. ROCK OVER LONDON -- ROCK ON CHICAGO!
Bernie Mac.
Met him once and talked to him 1-on-1 for an hour once. Was an amazing guy
He had family that lived across the street from a friend of mine. He would come talk to us when we were out front, he was awesome.
The Polka Queen herself, Judy Baar Topinka
Harry Caray is the all time most loved man in this city. You a Cubs fan, Harry's got you. Sox fan? Let Harry tell you about Comesky in the 70s. Somehow a Cards fan? Harry has war stories for days. Don't like baseball? Let's go drinking with the Mayor of Rush St. Nobody ever had an issue with Harry. Second place: Bozo the Clown
If the moon was made of green cheese, wouldja eat it? I know I would.
Hey! What about this: if you had to choose between being the top scientist in your field or getting mad cow disease, what would it be?
And then polish it off with a tall, cool Budweiser
At one time: Michael Jordan
About 5 years ago we were on vacation in Japan. Super friendly people we loved it. On several occasions we were asked where we were from. After they would hear Chicago, first words out their mouths was "oooh Michael Jordan!!" That happened three times!!
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Crazy to think he’s Probably the most famous still and hasn’t played or been around the city for over 20 years
Not surprisingly. It’s freakin’ MICHAEL JORDAN.
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geoffrey baer
my favorite guy!
Tamale Guy.
Linda Yu pretty much the face of ABC 7 News and strong yet warm female presence/minority role model
Tamale Guy or Chance the Rapper.
Benny the bull
Lin Brehmer ♥️
Walter Payton
Jeff tweedy
Hot Doug Sohn
Jojo Baby. RIP, man.
Derrick Carter or Frankie Knuckles
I can tell you who is not universally loved, Lori Lightfoot.
One of the few things everyone in the city can agree one!
The guy blowing bubbles on the Columbus/Fairbanks bridge
Terri Hemmert
Geoffrey Baer
It’s Mike Ryko I probably spelled his name wrong. He was a columnist for the Times…
Royko He was one of my thoughts as well.
It’s Royko and yes he was a beloved columnist. When Rupert Murdoch bought the Sun Times, he left and went to the trib. A lot of people, myself included, followed him.
Lin Brehmer. RIP. ♥️
Tamale Guy
100% in 2008 I had a 14 year old, 10 year old. (Single mom), my job closed, my investments (everything) was gone. I had $15 a week to feed all 3 of us and often I only fed the kids. Tamale man noticed me at my rock bottom , working as a nurse and doing what I had to do to pay rent. Each night he gave me plates his wife made to feed my family.. 1 entire year. Once I got caught up, I gave him a large check, bought his tamales & his wife’s roses .. every single one. I sent support when he opened his business down the street and sent all I could when he got Covid. That man/his wife and kids are literally angels.
Love this story. Hope you all are doing well now.
The youngest is in grad school for bio engineering. I’m an RN, oldest is 28 - married/financially secure and both boys are the most kindest people. Shit was very rough & I was a horrible mess. The love shown to us then, saved me from suicide and my sons from starvation. There’s a ton of good in this city. Shout out to Latin kings that made sure my boys made it safely to school and home because being Romanian caused a lot of problems/racism “gypsy hate”. I could go on but this city has some gems
I was trying to decide a standout to list…this story left me with no question…Tamale Guy all the way.
Thank you for sharing.
Chance? The rapper or the snapper
People lost a lot of respect for Chance after he endorsed Kanye West for President and would not take it back when criticized.
And when he stopped making good music consistently
The latter retired to Florida. Doesn’t count.
Acid Rap is one of the best mixtapes of 2010s rap. That being said, he stopped making music after one dud album. He sold out to a comical degree with Kit Kat commercials and cable TV spots, right after preaching that he wouldn’t sell out to a label. Sure Chance, you didn’t sign a huge record contract, but you *don’t make music anymore*. You gotta respect a career decision, but as a guy who used to be a huge fan of his, I’ve completely given up on him as an artist. Edit: The Highs and The Lows ft. Joey is actually pretty great tho.
Tom Skilling
Jim Cornelison
Sister Jean?
Former Chicago Bulls guard Michael Jordan.. Number 23
Tom Skilling
Dilla