picadilly palare?
thats a good one.
waterloo sunset.

although its not strictly about the town, cathedral by CSNY, is amazing, as its about david crosby having a bad acid trip in winchester cathedral and imagining that the paintings of jesus are oppressing him. ACE.

You're going to have to yousend me some of this Taxi Girl stuff...

London - William Blake (being covered by Sparklehorse)

"I wandered through each chartered street, near where the chartered Thames does flow, and marking every face I meet, marks of weakness, marks of woe..."

is about British cities (Coventry in particular) in the early 80s after the heavy industries were closed down and the social unrest that followed.

I think that's the best song about a town ever. Also the best number one ever, as it was one of those times when a hit single captured the mood of the nation. Or zeitgeist, if you're feeling intelligent.

"Once upon a time, not too long ago, we took a day out in Manchester
We all fall down, there's not enough hours in our day"

whippin' picadilly by gomez

but i havent listened to it for ages

"I left my heart
In San Francisco
High up on a hill
It calls to meeeeeeeeeeeeeee

To be where little cable carsssssss
Fly halfway to the staaaaaaaars...."

- Petula Clark

is the only one that springs to mind.

i guess its not town-specific, but it nicely sums up what living in a cultural backwater is like

'Let's hear that string part again, because I don’t think they heard it all the way out in Bushnell', what a classic.

The Beach Boys

'they got the sun in the summer, and in winter time the skiing is great'

The Times

by Defiance, Ohio.
S'about urban sprawl destroying all the things that made their childhood homes unique, creeks behind their houses, lots of open space, paving over an old graveyard to build a stripmall (And I wonder: what did they do with the bodies?}; basically putting housing into a grid system until everything is boring and cookie cutter.

I hang my head down on Hollywood
'Cause either way you look down it's just stars
And I'm making my way down the Cherokee
To get drunk in a bar
And I know my friends, they worry about me
I can see it written on their face
Despite anything that I said before
The bar is a beautiful place. . . . sha na na na, sha la la la la.

I got a cold in my heart that the doctor can't feel
He said "go get you a beer"
But they don't let the sunshine come in here.
Sha la. Sha la la la

Where the hookers and thieves and the junkies play
It's a circus round here for sure
And I worry about how I'm fitting in
If I only had her
And I know my friends they worry about me
I can see it written on their face
But despite anything I might have said before,
The bar is a beautiful place. . . . sha na na na, sha la la la la.

Ain't it strange, I see your face in the window of a store
Holding me back from throwing my bottles out at the cars
Sha la. Sha la la la

So hey there, Mrs. Samuels
Hey Laura, I'm thinking of you
Would you take an old drunk as-is
If he was sweet to you
And tomorrow, you'll probably give up on me
I won't blame you, hell I'll celebrate
'Cause despite anything you may have said to me
The bar is a beautiful place.

The Go-Betweens

'This Town Ain't Big Enough for the One of Me' by the Frank Turners (tis about winchester don't you know).

Also, 'Moving to Blackwater' by Reuben (only because I lived in the famous Blackwater at the time)