My Old School
Steely Dan Lyrics


Jump to: Overall Meaning ↴  Line by Line Meaning ↴

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
I was smoking with the boys upstairs when I
Heard about the whole affair, I said oh no
William and Mary won't do

Well, I did not think the girl
Could be so cruel
And I'm never going back
To my old school

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
Well, I hear the whistle but I can't go, I'm gonna
Take her down to Mexico, she said oh no
Guadalajara won't do

Well, I did not think the girl
Could be so cruel
And I'm never going back
To my old school

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
Well I hear the whistle but I can't go, I'm gonna
Take her down to Mexico, she said oh no
Guadalajara won't do

Well, I did not think the girl
Could be so cruel




And I'm never going back
To my old school

Overall Meaning

The lyrics of Steely Dan's "My Old School" are filled with a sense of nostalgia and bitterness. The song tells the story of a narrator who has left school and is reminiscing about a past relationship. The opening lines describe a time when the singer was leaving school, and the people he knew said goodbye to him. The song then takes a darker turn as it reveals that the singer's girlfriend has been arrested for prostitution, and the singer feels betrayed.


The lyrics convey a sense of regret and resentment towards the past. The song is filled with imagery that paints a picture of a faded youth that is now lost. The chorus is a powerful statement of this feeling: "Well, I did not think the girl could be so cruel, and I'm never going back to my old school."


The use of the names "William and Mary" and "Annandale" suggest that the song is set in the East Coast and possibly in the 1960s or 1970s. The singer's sense of disillusionment is heightened by the sense that the world that he once knew has changed, as suggested by the line "California tumbles into the sea."


In conclusion, Steely Dan's "My Old School" is a hauntingly beautiful song that captures the angst and disillusionment of a generation disillusioned with the past. The song is filled with imagery and is a masterclass in songwriting and performance.


Line by Line Meaning

I remember the thirty-five sweet goodbyes
I recall the thirty-five fond farewells we exchanged.


When you put me on the Wolverine up to Annandale
You ushered me onto the Wolverine en route to Annandale.


It was still September
The month was September at the time.


When your daddy was quite surprised
Your father was utterly taken aback.


To find you with the working girls in the county jail
He found you associating with laboring women in a jail situated in the county.


I was smoking with the boys upstairs when I
While I was puffing a cigarette with the chaps up above, I


Heard about the whole affair, I said oh no
Caught wind of the entire ordeal, and exclaimed oh no


William and Mary won't do
William and Mary isn't an option anymore.


Well, I did not think the girl
Frankly, I never assumed the lass


Could be so cruel
Would act in such an unkind manner.


And I'm never going back
Furthermore, I have no intention of revisiting


To my old school
My previous educational institution.


Oleanders growing outside her door
Oleanders are sprouting by her doorway


Soon they're gonna be in bloom up in Annandale
They'll blossom in no time up in Annandale.


I can't stand her
I cannot tolerate her


Doing what she did before
Engaging in past behaviors


Living like a gypsy queen in a fairy tale
Living luxuriously akin a fairy tale's gypsy queen.


Well, I hear the whistle but I can't go, I'm gonna
Although I heard the whistle, I can't go as I fully intend to


Take her down to Mexico, she said oh no
Transport her southward to Mexico, which she promptly denied.


Guadalajara won't do
Guadalajara isn't suitable, either.


California tumbles into the sea
California plunges into the ocean


That'll be the day I go back to Annandale
That's when I'll revisit Annandale.


Tried to warn you
I endeavored to alert you


About Chino and Daddy Gee
About Chino and Daddy Gee


But I can't seem to get to you through the U.S. Mail
Yet, you seem unreachable via U.S. Mail.


Well I hear the whistle but I can't go, I'm gonna
While I heard the whistle, I'm still going to


Take her down to Mexico, she said oh no
Carry her off to Mexico, to which she retorted with a no.


Guadalajara won't do
Guadalajara also won't suffice.


Well, I did not think the girl
Truly, I never believed the female


Could be so cruel
As capable of such malevolence.


And I'm never going back
As a result, I have no desire to return


To my old school
To my old learning institution.




Lyrics © Universal Music Publishing Group
Written by: DONALD JAY FAGEN, WALTER CARL BECKER

Lyrics Licensed & Provided by LyricFind
To comment on or correct specific content, highlight it

Genre not found
Artist not found
Album not found
Song not found

More Versions