A 2006 Entertainment Weekly article, “Back to Annandale” explains the backstory of “My Old School.”
But just outside of Adolph’s, he sees it. The house. ‘'Right there is the house that I was busted in,’‘ [Donald Fagen] says, gesturing toward a two-story structure nearby. Here, finally, lies the sto...
[Verse 1]
I remember the thirty-five sweet goodbyes
When you put me on the Wolverine
Up to Annandale
It was still September
When your daddy was quite surprised
To find you with the working girls
In the county jail
[Pre-Chorus]
I was smoking with the boys upstairs
When I heard about the whole affair
[Chorus]
I said oh no
William and Mary won't do, now
Well I did not think the girl
Could be so cruel
And I'm never going back
To my old school
[Verse 2]
Oleanders growing outside her door
Soon they're gonna be in bloom
Up in Annandale
I can't stand her
Doing what she did before
Living like a gypsy queen
In a fairy tale
[Pre-Chorus]
Well I hear the whistle but I can't go
I'm gonna take her down to Mexico
[Chorus]
She said whoa no
Guadalajara won't do, now
Well I did not think the girl
Could be so cruel
And I'm never going back
To my old school
[Instrumental Break]
[Verse 3]
California tumbles into the sea
That'll be the day I go
Back to Annandale
Tried to warn you
About Chino and Daddy Gee
But I can't seem to get to you
Through the U.S. Mail
[Pre-Chorus]
Well I hear the whistle but I can't go
I'm gonna take her down to Mexico
[Chorus]
She said oh no
Guadalajara won't do, now
Well I did not think the girl
Could be so cruel
And I'm never going back
To my old school
[Instrumental Outro]
My Old School was written by Donald Fagen & Walter Becker.
My Old School was produced by Gary Katz.