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This was PROBABLY from the 90s, or 00s, although I couldn't swear to it. I used to confuse it with Meatloaf's 'Objects in the Rearview Mirror', but there are only some overlapping elements.

The singer was young (probably too young to drink) and shows up at some kind of part that is shortly afterwards broken up (by the police, I think.) While everyone scatters, a (rather misunderstood, I think) young lady with a dubious reputation offers him a ride (I want to say somewhat teasingly/sarcastically - 'C'mon; get in.'), and I believe his perception of her changes/deepens as a result of the ride.

I want to say it's Pearl Jam, or someone similar, but I can't seem to find it. As I recall, it's kind of melancholy and reminiscent, but that could just be how I'm remembering it.. Any thoughts?

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I managed to recall it while trying to think of how to describe the tone, and I'll leave it, just in case someone else has the same question...

It's Johnathan Coulton's 'Town Crotch' from his Thing a Week. Like many of his silly songs/parodies, it actually not a bad song, if you ignore the slightly ridiculous title / premise.

http://youtu.be/K8Bh6ezlG8Q

Lyrics:

The seniors threw a party down the end of Dutton Road
It was almost cold enough to snow
None of us could drive then so we had to get a ride
In the back of someone's GTO

She was in the keg line with a yellow plastic cup
It was like I'd never seen a girl before
Puffy leather jacket and a healthy head of hair
With the hair she was six foot four
I recognized her face right away

She was the town crotch
She was good to go anytime
She was the town crotch
But I loved her like she was mine
There's a lot of things I don't remember now
But I remember the town crotch
And I remember the town crotch

I had a pint of So Co in the pocket of my coat
You can hardly taste the alcohol
Watched her from a distance but I never said a word
I was young and I felt so small
I was no-one then, who was I?

She was the town crotch
She was good to go anytime
She was the town crotch
And I loved her like she was mine
There's a lot of things I don't remember now
But I remember the town crotch (I remember the town crotch)

We stood around and drank a lot and leaned against the cars (I remember the town crotch)
Tried to beat the winter, made it just under the wire (I remember the town crotch)
Got drunk and loud under a thousand million stars (I remember the town crotch)
Someone played Steve Miller, someone set some stuff on fire

The cops came by to bust us so we left the beer and ran
My head hurt and I couldn't find my ride
She pulled up in a Gremlin and she rolled the window down
She said "Hey kid, get inside."
Then she asked my name and drove me home

She was the town crotch
She was good to go anytime
She was the town crotch
But I loved her like she was mine
There's a lot of things I don't remember now
But I remember the town crotch
Yeah I remember the town crotch
Yeah I remember the town crotch

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