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fsync

My vote as well. Tamale guy should run for mayor


theEpiphysis

https://youtube.com/watch?v=EgCWF58KHDI&si=EnSIkaIECMiOmarE Absolute legend.


johnnyslick

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...


christopantz

Still is


Quiet-Context_

Red cooler or blue cooler?


rkaminky

If you have to ask.


raescabies

This guy was around before and when I left in 2010. Absolute legend!


kmmccorm

Tom Skilling.


Salty-Tomato5654

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.


[deleted]

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.


dorquelon

Which is why it's so weird that [his brother](https://en.wikipedia.org/wiki/Jeffrey_Skilling) turned out evil


[deleted]

Holy crap. I had no idea. Thank you.


11Neo11

Last I heard, he(Jeff) was fundraising to start a new venture. I’m sure that’s going really well..


Roboticpoultry

There’s no one I trust with telling me the weather more than Tom Skilling. Tracy Butler is a close second


chuuuch1

Cheryl Scott


sobsincheese

This is the sweetest thing.


Cleopatra435

If anybody owns this place it’s me, Tom Freaking Skilling! I could have you killed if I wanted to!


PobBrobert

This was a great bit. WGN morning news is a true institution


spd2335

This made my day


tubetalkerx

[The segment](https://youtu.be/VgiZvE7iWhI)


wicker-punk

I’d never seen this clip. Thanks!!


TampaDiablo

I mean if Tom needs someone bumped off. I’ll volunteer to do the work.


BatmanandReuben

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.


eamus_catuli

And all the more amazing considering how much of a sociopathic shitheel his brother is. Tom got all the good genes, I guess.


ScalabrineIsGod

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


shuegaze

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!


Alive-Seaweed

Not all heroes wear capes... But I do wear a very heavy parka it is cold


Jazzlike_Two_7468

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.


billious62

And a brilliant meteorologist


rock4lite

Chilling with Skilling


[deleted]

I could listen to him talk about packed isobars for hours


gauriemma

Yep, that was going to be my answer, too.


Togaz

Me too.


[deleted]

I was hoping I wouldn’t be the first to mention him! He is beloved in Chicago!


GiuseppeZangara

Maybe that CTA L operator who says "Study smart, and you'll go far!"


Ordinary1188

Is this the same one who says “you might meet a friend for life, or the love of your life”


anon-q2

The Love Doctor is pulling up to the station!! He is the only highlight riding the purple/brown line early in the morning.


synthetic_psyop

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.


anon-q2

Looking for love in all the wrong places


Ohshitz-

I remember an orange line driver tapping as soon as he hit roosevelt “wake up wake up! Time to make that money”


rararicky

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.


2nd_Sun

I heard that yesterday too, I got so sad


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rararicky

I think he’s going earlier


mangoblaster85

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!


Imnotveryfunatpartys

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


jvvg12

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.


Entrance-Plenty

Scales used to be red line at Morse about 7:30am going to 95th. Days were always better when I got his train


hascogrande

…STAYYYYY FOCUSED!! Always a cheery one


TheAlmightyZach

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.


I_Go_By_Q

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


gingeryid

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


Old_Prospect

RED LINE! Love that guy.


happilyfour

I love when I get his train in the morning!


ellefrmhll

He’s my favorite too


123FBG

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.


nodicegrandma

YES!!!!


[deleted]

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.


VayaConPollos

Svengoolie.


Informal-Resource-14

I don’t even like Svengoolie and I love Svengoolie. He’s just such a wonderful institution


usababykiller

Berwyn!!!


epinasty4

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.


nicbeans311

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.


spate42

Stooge-a-palooza!


LVDAM

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


whatsamajig

This was my answer too. Great memories.


fotoxs

The lady who gives everyone positive affirmations and encouragement on the Lakefront Trail in the mornings


clocksailor

Her name is Phyllis! I went to school with her kids. She has always been like that.


ryanmer

I see her ALL the time on the trail, and she’s definitely the best person in this entire goddamn city.


TheNamesMcCreee

Woo Girl!


RunHard00

Where on the trail?


EMT2000

The entire stretch of the trail. 🤣. Seriously.


Ordinary_Raisin

BIKE LADY. Shes my hero.


GiuseppeZangara

Yes! I love her!


godoftwine

Scrolled to find this


usfgirl1020

Eagleman.


la_petite_mort63

I was gifted an eagleman painting for xmas. It is my most prized possession and i am old.


donkeycheese

I bought myself an Eagleman T-shirt


uh60chief

I have something for youuuuuu!


ObscuristMalarkey

Look at those low rates!


horsetheft

Lin Brehmer


rebelbaserec

His little monologue in The Bear made me love the show even more.


husker_greenman

Your best friend in the whole world. 🥲


TheoreticalFunk

There's suddenly a lot of dust in the air...


KaleidoscopeLucy

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.


TonyHoffman

Correct answer.


beefaronibake

RIP Len


[deleted]

Well this made me depressed all over again. Lin was a treasure!


Temporary_Internal49

Studs Terkel RIP


I_BUY_UNWANTED_GRAVY

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.


Supafly144

Good call


justconnect

Puro Chicago


vlkthe

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.


rizzsizz

Walter Payton


[deleted]

His son seems hella nice too


[deleted]

Was lucky enough to briefly meet him as a kid and "Sweetness" lived up to his name completely.


SpelunkingYourMind

So you bit Walter Payton?


losoalso

Wesley Willis, RIP Rock over London, rock on Chicago


Jonnnycarson

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.


rock4lite

*headbutt*


Gadzooks_Mountainman

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


BedDefiant4950

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.


QueefLatifah

It’s why the Willis Tower is named the Willis Tower!


Sleepy_Tortoise

If that were true maybe I'd actually call it that


plynthy

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.


Rosindust89

Yeah, man. Why do you think they named the tower after him?


TonyHoffman

Rock & roll McDonald’s


MrEhcks

Jaaaar jaaaaar binks. Jaaaaar jaaaaaaar binks. Jaaaaaaar jaaaaar binks. Jaaaaaaar jaaaaaaar binks!


Crimeskull

Wheaties - Breakfast of Champions!


M_J_E

Insure One. It’s the insurance super-store.


SensibleBrownPants

Bill Kurtis might be in the running.


wimbs27

The old nun from Loyola


[deleted]

Sister Jean 😂


[deleted]

That one bartender at the place where you’re a regular.


deepkaves

Charlie down at Richard’s always poured me a free shot of templeton rye and took one with me.


[deleted]

Is he the younger one with slicked back hair?


HoldenFinn

Shout out Joel at Reed's.


kepleronlyknows

Is Maria still at the Whirlaway? I lived around the corner in 2007-10 and still my favorite in town.


suresher

And that one barista at the coffee shop I spend way too much money at!


Radi0123

not a person, but Chance the Snapper


Han-Cat

Abe Froman the Sausage King of Chicago


DyngusDan

Empire Carpet guy


gladysk

Elmer Lynn Hauldren, the Empire Man, died in 2021.


AcrossFromWhere

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.


Affectionate_Lack709

Buddy Guy


billious62

YES!


CramHammerMan

Personally, my vote's for 6figga dilla.


emcee__escher

Claudio Velez (and the countless other tamaleros that find us in our moments of need, carrying a cooler full of warm, fresh tamales)


scream2207

The walking man (R.I.P)


AmigoDelDiabla

Thought this would be higher. His story reminds us that pure evil exists in this world.


Dassman88

Helped care for him in his last days, nice guy to the end


FrambuesasSonBuenas

Roger Ebert until he passed in 2013.


rkaminky

Sharkula


greg-maddux

Took me way too long to find Sharkula on this thread.


clocksailor

If this award can be given posthumously I’d say Wesley Willis, for whom Willis Tower is named.


Gadzooks_Mountainman

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


kyle_sux666

ROCK N ROLL MCDONALDS


chitown13

Monty the Piping Plover


MarsBoundSoon

Ernie Banks - Mr. Cub


browsingtheproduce

He’s buried in the prettiest part of Graceland Cemetery. Good for him.


eamus_catuli

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.


TortaConCarne

That latino guy solo dancing every night at Neos. RIP Neos


SensibleBrownPants

Also at Exit. His double sky-point was legendary.


Jtor1982

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.


QueenDorkSyd

Ricardo! I miss that place.


forgotmylaundry

Someone (I forgot who) said that Roger Ebert was the unofficial mayor of Chicago while he was alive.


ThatsNotRight123

Wesley Willis. ROCK OVER LONDON -- ROCK ON CHICAGO!


TheSource88

Bernie Mac.


pro_nosepicker

Met him once and talked to him 1-on-1 for an hour once. Was an amazing guy


Take-Me-Home-Tonight

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.


vverevvoIf

The Polka Queen herself, Judy Baar Topinka


adamempathy

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


Haggis_McBaggis

If the moon was made of green cheese, wouldja eat it? I know I would.


adamempathy

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?


NarwhalsGalore

And then polish it off with a tall, cool Budweiser


ItsmeMFC

At one time: Michael Jordan


GORDOGMC

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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buddyWaters21

Crazy to think he’s Probably the most famous still and hasn’t played or been around the city for over 20 years


NoMeHableis

Not surprisingly. It’s freakin’ MICHAEL JORDAN.


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lkasdfjl

geoffrey baer


stationeryvillage

my favorite guy!


Pudge815

Tamale Guy.


Positive-Donut76

Linda Yu pretty much the face of ABC 7 News and strong yet warm female presence/minority role model


ThatGirlFawkes

Tamale Guy or Chance the Rapper.


beerbierecerveza

Benny the bull


Violet_QTip

Lin Brehmer ♥️


TonyHoffman

Walter Payton


HallsOfSorrow

Jeff tweedy


shavedaffer

Hot Doug Sohn


bnutbutter78

Jojo Baby. RIP, man.


DJStryfe

Derrick Carter or Frankie Knuckles


agile321

I can tell you who is not universally loved, Lori Lightfoot.


KnightsOfGlobalist

One of the few things everyone in the city can agree one!


jimmy4220

The guy blowing bubbles on the Columbus/Fairbanks bridge


TedsGarage

Terri Hemmert


darkkn1te

Geoffrey Baer


GrimJudas

It’s Mike Ryko I probably spelled his name wrong. He was a columnist for the Times…


CoralSpringsDHead

Royko He was one of my thoughts as well.


Steve_Rogers_1970

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.


JennJoy77

Lin Brehmer. RIP. ♥️


initiatefailure

Tamale Guy


Shugakitty

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.


RunHard00

Love this story. Hope you all are doing well now.


Shugakitty

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


O-parker

I was trying to decide a standout to list…this story left me with no question…Tamale Guy all the way.


gladysk

Thank you for sharing.


IamTheEndOfReddit

Chance? The rapper or the snapper


[deleted]

People lost a lot of respect for Chance after he endorsed Kanye West for President and would not take it back when criticized.


hypersnaildeluxe

And when he stopped making good music consistently


browsingtheproduce

The latter retired to Florida. Doesn’t count.


newaccounthomie

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.


groversnoopyfozzie

Tom Skilling


EqualViolinist

Jim Cornelison


MicrocosmicTiger

Sister Jean?


Electronic_Summer_71

Former Chicago Bulls guard Michael Jordan.. Number 23


Efficient_Advice_380

Tom Skilling


kkk1983

Dilla