You know that “Down on Main St.” song by Bob Seger?
Allegedly it’s about Main St. in Ann Arbor, MI – my adopted hometown, where I attend college.
It’s kind of sad, the song doesn’t really paint a good picture of the Ann Arbor I know… it makes it sound kind of slummy. Oh well. We hear that song from time to time.
Bad Company also had a (different) song called "Oh Atlanta. "Alison Kraus does a cover which is really nice.
Atlanta also gets brief mentions in “Love Shack” by the B52s and “200 More Miles” by The Cowboy Junkies, and then there’s “Doraville” (which is in metro Atlanta) by Atlanta Rhythm Section.
“Rainy Night in Georgia” by Brook Benton is obviously set in Atlanta, though he doesn’t mention the city’s name.
Going back eight decades, Jimmie Rodgers had some unfavorable commentary on my fair city in “T for Texas (Blue Yodel No. 1”
The only one of those songs I got really sick of hearing was “Doraville” (though it seldom gets played any more).
"I never sleep, cause sleep is the cousin of death"
The late John Denver used to sing a song called Saturday Night in Toledo, Ohio but nobody in Toledo took it too kindly. 
Mass Ave. by Wille Alexander is a great Boston song.
Source: Philadelphia Freedom (song) - Wikipedia
I’ve heard this and similar comments for years about the song, just as I heard that it is not about the city of Philadelphia, per se.
The only one that comes to mind for Regina is by the Arrogant Worms’ song The Last Saskatchewan Pirate. A verse of the total lyrics which can be found here :
Cause it’s a Heave! Ho! Hay! Ho! Comin’ down the plains
Stealin’ wheat and barley and all the other grains
It’s a Ho! Hay! Hi! Hay! Farmers bar your doors
When you see the Jolly Roger on Regina’s mighty shores
It is not overplayed on the radio here. I hear it infrequently, at best, though I enjoy it when I do.
I have lived my early years in a city called “Finland’s Chicago”, so my city song is naturally Sweet Home Chicago (especially the Blues Brothers version).
And The Reader was located in…?