About the song
Steely Dan’s “My Old School” is more than just a catchy rock tune. It’s a sardonic look back at a tumultuous time for the band’s core members, Donald Fagen and Walter Becker. Released in 1973 as the second single from their album “Countdown to Ecstasy,” the song delves into a real-life incident that forever marked their college experience.
The lyrics paint a vivid picture of a drug raid that swept through Bard College in May 1969. Referred to only by its location, “Annandale,” the song recounts the betrayal of a female acquaintance who tipped off the authorities, leading to the arrest of approximately 10% of the student body. News reports of the time placed the number at around 44 students, a significant disruption for the small college. The song hints that Fagen himself was among those arrested, with a wry reference to his long hair being shorn off in jail.
Despite the seriousness of the event, “My Old School” takes a surprisingly upbeat musical approach. This stylistic contrast is what caught the attention of critics, who described it as a “departure” for the band. The song’s jaunty melody and playful vocals belie the anger and disillusionment simmering beneath the surface.
“My Old School” holds a unique place in Steely Dan’s history. It’s a personal story, offering a rare glimpse into the lives of the band’s masterminds before they achieved musical fame. The song’s lasting legacy extends beyond the music itself. In a later twist, Fagen would break his vow of never returning, accepting an honorary degree from Bard College in 1985. “My Old School” serves as a reminder of Steely Dan’s ability to weave personal experiences into captivating music, leaving listeners both entertained and intrigued.
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Lyrics
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