what is Steely Dan's "My old school" about?

[Freejooky]

Link to lyrics - http://www.guntheranderson.com/v/data/myoldsch.htm

Is it that the girl is rich and snooty? Too demanding? Uppity?

[I_can_t_believe_that_s_butter]

This may or may not help—

Becker and Fagen purposefully (according to the Taxicab Confessions episode, moreso Fagen) obscure the meaning behind the lyrics of their songs.

That said, there seems to be a good deal of on-track speculation here.

[Antonius_Block]

It might be worth noting (although you may already be aware of this) that Becker and Fagen met when both were attending Bard College in Annandale-on-Hudson (up the Hudson River from NYC). In those days there was a train called the “Wolverine” that went from NYC to Chicago via Detroit (hence the Michigan reference in the train’s name) and stopped at a station near Bard College, hence:

I remember the thirty five sweet goodbyes
When you put me on the Wolverine up to Annandale

.

[Antonius_Block]

More analysis [here](http://www.feverdreams.net/countdo.htm#My Old School):

There was an unpleasant drug bust at Bard in May of 1969, according to Brian Sweet, and both Mr. Becker and Mr. Fagen were apprehended (RITY, p. 15)–thus, presumably, the reference to ending up “with the working girls in the county jail.” Historical note: G. Gordon Liddy was the assistant D.A.

Yes, that G. Gordon Liddy.

It was also at Bard that Becker & Fagen hooked up with a fellow student who was their drummer for a while: Cornelius Crane Chase (scion of the Crane plumbing-fixture family), aka Chevy Chase, later of SNL fame.