Song Lyric Sunday: Two “Chicago” Songs

Given Jim’s bunch o’ prompt words for today, "City, Country. County, State, Town" (which I understand come from Lisa over at Our Eyes Open – thanks, Lisa!), two songs jumped immediately to mind, and of course you know what they are…

The first is "My Kind of Town (Chicago Is)," written by Jimmy Van Heusen with lyrics by Sammy Cahn for the 1964 Rat Pack movie "Robin and The Seven Hoods," starring Frank Sinatra, Dean Martin, Sammy Davis Jr., and Bing Crosby, as well as Peter Falk, Barbara Rush, and Edward G. Robinson (who didn’t get a credit). The song received an Academy Award nomination for Best Original Song, losing out to "Chi Chim Cher-ee," from the movie Mary Poppins. It only reached #110, but it’s still a classic. The Wrigley Building is still on Michigan Avenue on the north bank of the Chicago River, but the Union Stock Yards closed in 1971. Only the Union Stock Yards Gate remains, having been named a National Historic Landmark forty years ago yesterday. Mary’s family all worked in the Stock Yards at one time or another, and she grew up in the Back of the Yards neighborhood (I also lived there after we were married).

The Crazy Crooner, who posted the song, also posted the lyrics.

Now this could only happen to a guy like me
And only happen in a town like this
So may I say to each of you most gratef’lly
As I throw each one of you a kiss

This is my kind of town, Chicago is
My kind of town, Chicago is
My kind of people, too
People who smile at you

And each time I roam, Chicago is
Calling me home, Chicago is
Why I just grin like a clown
It’s my kind of town

My kind of town, Chicago is
My kind of town, Chicago is
My kind of razzmatazz
And it has all that jazz

And each time I leave, Chicago is
Tuggin’ my sleeve, Chicago is
The Wrigley Building, Chicago is
The Union Stockyard, Chicago is
One town that won’t let you down
It’s my kind of town

The second song is "Chicago (That Toddlin’ Town)," written by Fred Fisher in 1922. It’s been done many, many times, but the most famous is the one by Frank Sinatra, from 1957. I’m sure there are some of you want to know who Billy Sunday is, so click the link.

The lyrics, from

Chicago, Chicago, that toddling town
Chicago, Chicago, I will show you around,I love it
Bet your bottom dollar you’ll lose the blues in Chicago, Chicago
The town that Billy Sunday couldn’t shut down

On State Street, that great street, I just want to say
They do things they don’t do on Broadway
They have the time, the time of their life
I saw a man, he danced with his wife
In Chicago, Chicago, my home town

Chicago, Chicago, that toddlin’ town
Chicago, Chicago I’ll show you around, I love it
Bet your bottom dollar you lose the blues in Chicago, Chicago
The town that Billy Sunday could not shut down

On State Street, that great street, I just wanna say
They do things that they never do on Broadway, say
They have the time, the time of their life
I saw a man and he danced with his wife
In Chicago, Chicago, Chicago
That’s my home town

And that’s Song Lyric Sunday and Song of the Day for May 30, 2021.

36 thoughts on “Song Lyric Sunday: Two “Chicago” Songs

  1. oh my gosh, yes it is! MY KIND OF TOWN…. CHICAGO WAS…. Sorry not today…. may be it will one day again, but it isn’t now. This blogging is really getting me down… I’ve been so depressed about it that it has brought me to tears. I never thought it would actually get me this depressed. I thought I’d really could make it for today, but it’s not so good, and yes my blog is up for Monday…. but it’s so tiny… just not what I wish it could be. I guess I’ve lost my brains some place… people give me information and directions how to do things and it’s like following ABC, BUT I guess I’m in numerical mode. I donno… it’s really depressing! Oh hell, I was a damn paralegal at one time helping my boss win cases, but this THIS is bringing me down. BUMMER! Anyway, I need to fix it up (my blog), but it’s posted, but I’m sure if I am less tired I’ll be able to fix it better. Please stop by and maybe you can give me some pointers please?????? Thanks JOhn and Happy Memorial Day! Have fun and don’t eat too much! hehehehe hugs…. and come on over I got a dog or brat on the barbie for ya! hahahaha Bring your lovely wife also! Have fun today!


    1. Chicago sure has gone to hell in the time we’ve lived here. The good parts got better, the bad parts got much worse.

      I know, they threw the block editor at you and it’s driving you crazy, right? I’ve finally made peace with it by using as little of it as I can. Supposedly you can use a “Classic” block and it’ll work just like the old one did. I should try it out…

      Liked by 1 person

  2. It is interesting you bring up that Mom didn’t seem to have a Sinatra album. Perry Como? Yep. Andy Willams? Of course. Johnny Mathis? You betcha. No Sinatra or any Rat Pack member. You’d be in a better position to say why. I remember Mom loved the Cats! album and the Sleepless in Seattle soundtrack later on. And of course always Moon River from Breakfast at Tiffany’s. My dad? He loved Mack the Knife.


    1. Your guess is as good as mine. She liked the crooners, which was Sinatra for certain and Dean and Sammy might fit into that category, but she didn’t like them. Ulysses S. Grant once said that he liked two songs, one was “Yankee Doodle” and the other wasn’t, and it was kind of like that with your dad. One of the priests at St. Ignatius had a big collection of Longines Symphonette Society albums, and when he died your dad laid claim to them. I remember Mom really liked “Beautiful Music.” Back when I was in high school, there was WAIT on AM and WFMF/WLOO, WCLR, and WLAK on FM, and the radio on the living room was usually on one of those. Oh, another one your dad liked was “Bad, Bad, Leroy Brown”…


      1. Great memories, thanks for sharing. I think Mom would have loved if we were talking about this in that living room with her and our other brothers. Manhattans for all! Appreciate that steel trap memory of yours, John….


  3. Two very good Sinatra songs. I don’t go out of my way to listen to Sinatra, but it’s nice when I do hear something from him. Never been to Chicago, though. What a history that city has had. 🙂


  4. I find it funny that the first song lost to Chim Chim Cher-ee because My Kind of Town is better, I think and I am not a huge fan of Sinatra. So many great building faced the wrecking ball which is a shame. I know the second song well but prefer Judy Garland’s version.


  5. I can’t listen to Frank all of the time but I do like him. These two sound really good.


  6. Chicago and Frank Sinatra! You no how to touch my heart on this Memorial Day weekend, John. Have a good weekend. Our best to Mary.


  7. I saw Chicago once, from a distance. I was in a semi-truck (big rig) and apparently, such vehicles, if not banned, had a hard time in Chicago because of the low train overpasses (the El?) and the layout of the roads overall. I was happy not to get all the way in there, it was smoggy. Looked cold. But great shares John!! Anything by Frank Sinatra is a classic!


    1. Some of them are the “L,” others are freight and commuter trains. There are viaducts all over Chicago (“Why a duck? Why not a chicken?”). There might be a few that really do nothing, but they leave them up because someone might start using them again. For example, the train from Midway Airport to downtown used all old tracks from the Chicago Belt Line Railroad. (That’s a railroad that exists to move things between rail yards. Remember, Chicago was a huge railroad hub.) Glad you liked the songs!


  8. Ahhh, another two great songs and perfect choices for today. I don’t think my parents were Sinatra fans because we did not have any of his records at all. Odd considering how many others of that genre they enjoyed.


    1. I don’t recall my parents having any Frank Sinatra albums, either. They liked him well enough, but realy didn’t prioritize record buying. They had a couple by Andy Williams and a couple by Jack Jones….

      Liked by 1 person

  9. I’m not familiar with either of those songs, but they are smooth, easy listening – I played both all the way through when I fully intended to just listen to a snippet because I have to rescue dinner from the oven (I called out for The Hub to get it out instead). Nice choice!


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