“Cleveland Rocks” and “Dirty Water” (Boston) are two of the greatest ever rock songs commemorating cities.
I would respectfully submit “New York Groove” (especially this version) as the quintessential NYC song (used to great effect in the movie “American Animals”).
Kentucky cities have just one realistic entrant as far as I know - “Bowling Green” by the Everly Brothers.
I’m pretty far from Detroit, but still in the outskirts of the greater Detroit Metro area, so I guess it’s ‘my’ city.
Sammy Davis Jr. did ‘Hello Detroit’, a ‘Sinatra sings New York New, York’ style anthem.
If you want something that rocks out more, there’s ‘Detroit Rock City’ by KISS.
Mitch Ryder did a cover of this song, substituting Detroit for Boston, that used to get a lot of airplay on the Detroit rock stations. So for years I thought it was originally written about Detroit.
Chicago, Chicago that toddling town
Chicago, Chicago I will show you around
I bet your bottom dollar you’ll have some fin in Chicago, Chicago
The town that Billy Sunday couldn’t shut down
On State Street, that great street, I just like to say
They do things they don’t do on Broadway
You’ll have the time, the time of your life
I saw a man who danced with his wife
In Chicago, Chicago my home town
Chicago, Chicago that toddlin’ town
Chicago, Chicago
Bet your bottom dollar you’ll have some fun Chicago, Chicago
The town that Billy Sunday could not shut down
On State Street, that great street, I just want to say
You’ll see things won’t see on Broadway
I have the time, the time of my life
I saw a man who danced with his wife
In Chicago, Chicago, Chicago, my home town
Agreed, though these days, I think there’s a correlation between people who listen to Chicago’s classic rock stations, and those who know the song (though it did appear in the second Guardians of the Galaxy film).
I only just recently learned (I believe via a Curious City segment on Chicago Public Radio) that the “toddlin’” in “toddlin’ town” refers to a dance craze called “the Toddle.” I just imagined it was a made-up word referring to the frenetic energy of a toddler, or something.