Tobacco Road
Bob Dylan (“Oxford Town”) and Phil Ochs (“You Should Have Been Down In Mississippi”) are not exactly raves about the state.
Nina Simone was not especially fond of the American South, while Mississippi was apparently at the bottom of her list.
Alabama’s gotten me so upset
Tennessee made me lose my rest
And everybody knows about Mississippi Goddam
Doesn’t paint a very good picture of NYC in that song either…
You make a good point.
Ry Cooder wrote a funny and accurate song about Hollywood. A clip of the chorus from Down In Hollywood pretty much sums up his opinion of the place:
“Down in Hollywood
You better hope that you don’t run out of gas
Down in Hollywood
They’ll drag you right out of your car and kick your ass
In Hollywood
They’re standing on the corner just waiting for a sucker like you
Down in Hollywood
Now if you want to stay healthy just keep 'em moving right on through”
Since the latter were from Jacksonville, Florida, I always wondered if the erm ‘inhalation’ for “That Smell” (mostly about drug addiction) was partially thanks to the northside paper mill, which I would often smell whenever we drove up I-95 as a kid (usually to the airport)
The local food does suck-a
The children run a-muck-a
(which has the poor song writing form of rhyming mucca with muck-a)
The Monkees’ Pleasant Valley Sunday makes a case that 1960s life in suburbia is staid and boring. Well, we can’t all be aspiring rock stars living in a Malibu beach house, driving a custom car, living the bohemian life, having adventures with monsters, spies, aliens, and the devil himself, without apparently any money, now can we? 
Though even today, 60 years later, I despise “rows of houses that are all the same”, which are every new development in Mesa, as well as probably everywhere.
Manfred Mann’s Hollywood Town is another song that doesn’t have a lot of good to say about the town.
No shortage of Texas songwriters detailing how much Dallas sucks, most classically Jimmie Dale Gilmore
“Well, Dallas is a woman who will walk on you when you’re down
But when you are up, she’s the kind you want to take around
But Dallas ain’t a woman to help you get your feet on the ground
And Dallas is a woman who will walk on you when you’re down”
And of course James McMurtry singing about Levelland which makes Lubbock look positively bumpy
“Flatter than a tabletop
Makes you wonder why they stopped here
Wagon must have lost a wheel or they lacked ambition one”
“Tillsonburg”: Stompin’ Tom remembers backbreaking work in the tobacco fields around Tillsonburg, Ontario.
“Leaving Las Vegas” doesn’t seem very Vegas-friendly.
“Downtown L. A.” by J. J. Cale – Describes life in the skid row part of downtown.
Johnny Cash has two songs with some choice shit-talking about Folsom Prison and San Quentin.
Pete Townshend’s White City is an entire album about the quiet despair of the people living in council estates in the eponymous, then-run-down London district. Pretty much any single song from the album qualifies, but the title track (with music and lead guitar by David Gilmour), narrated by an aging WWII veteran who now lives alone in a single-room flat and longs for the days when he was one of the youths fighting in the streets, is particularly bittersweet.
When British neo-mod / punk band The Jam moved from Woking to London they didn’t find it welcoming. As chronicled in the song Strange Town
TCMF-2L
TOKÉBAKICITTE – an extremely catchy song about some of the white trash, phonies and racist cops who live in Quebec.
