Meaning and Lyrics of My Old School by Steely Dan

Song Lyrics meaning of My Old School by Steely Dan

About Steely Dan

Steely Dan is an American rock band founded by Walter Becker and Donald Fagen in 1972. Known for their sophisticated jazz-influenced rock sound and cryptic lyrics, the band achieved critical and commercial success throughout the 1970s. Their music often features complex harmonies, intricate arrangements, and witty wordplay. One of their notable songs is My Old School, which was released on their 1973 album “Countdown to Ecstasy.” The track reflects the band’s characteristic blend of jazz, rock, and pop elements, combined with Fagen’s distinctive vocals and the duo’s meticulous production style.

Meaning of My Old School by Steely Dan

“My Old School” by Steely Dan recounts a personal narrative filled with vivid imagery and emotional depth. The song seems to be about a series of events in the past involving betrayal, heartbreak, and a sense of defiance.

In the first verse, the singer reminisces about a past departure marked by farewells and a train journey to Annandale. The mention of the daddy’s surprise at finding a loved one in a troubling situation adds a hint of scandal. The pre-chorus reveals that the singer was at a party when news of the betrayal reached him, enforcing the sense of detachment and disbelief.

The chorus expresses a deep rejection and disillusionment with the past. The line “William and Mary won’t do” suggests a refusal to return to a place or a state of mind associated with pain and deception. The singer feels deceived by someone they thought highly of, hinting at a painful lesson learned.

In the second verse, the imagery of flowers blooming and the mention of a ‘gypsy queen’ living a fantastical life juxtapose with the harsh reality of betrayal and hurt. The pre-chorus again hints at a desire to escape the pain by going somewhere far away.

The third verse introduces a reference to California sinking into the sea, a metaphor for a catastrophic event. The singer seems to express a feeling of inevitability and a distancing from the past, despite warnings that seem to fall on deaf ears.

Overall, “My Old School” reflects themes of betrayal, growth, and resilience. The song captures a moment of reckoning with past experiences, bitterness, and ultimately, a determination to move forward and not let the past define one’s future. The instrumental sections provide a space for reflection and contemplation, enhancing the emotional impact of the lyrics.

Lyrics of My Old School by Steely Dan

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

Discography Steely Dan

Everlasting Summer (Live)

Release: 2023-10-19
Label: Vision
1. Bodhisattva – Live 1974
2. The Boston Rag – Live 1974
3. Do It Again – Live 1974
4. Any Major Dude Will Tell You – Live 1974
5. King Of The World – Live 1974
6. Rikki Don’t Lose That Number – Live 1974
7. Pretzel Logic – Live 1974
8. Your Gold Teeth ll – Live 1974
9. Reelin’ In The Years – Live 1974
10. This All Too Mobile Home – Live 1974
Tracklist Collapse

University of California, Irvine, Ca March 10th 1974

Release: 2022-05-06
Label: Vision
1. Do It Again – Live
2. Rikki Don’t Lose That Number – Live
3. Any Major Dude – Live
4. King Of The World – Live
5. Barrytown – Live
6. My Old School – Live
7. Pretzel Logic – Live
8. Reelin’ In The Years – Live
9. This Is All Too Mobile Home – Live
Tracklist Collapse

NORTHEAST CORRIDOR: STEELY DAN LIVE (Live)

Release: 2021-09-24
Label: Geffen
l
1. Black Cow – Live From Mohegan Sun Arena
2. Kid Charlemagne – Live From The Orpheum Theatre
3. Rikki Don’t Lose That Number – Live From Mohegan Sun Arena
4. Hey Nineteen – Live From The Met Philadelphia
5. Any Major Dude Will Tell You – Live From Mohegan Sun Arena
6. Glamour Profession – Live From The Met Philadelphia
7. Things I Miss The Most – Live From The Beacon Theatre
8. Aja – Live From The Orpheum Theatre
9. Peg – Live From The Orpheum Theatre
10. Bodhisattva – Live From The Beacon Theatre
11. Reelin’ In The Years – Live From Mohegan Sun Arena
12. A Man Ain’t Supposed To Cry – Live From The Orpheum Theatre
Tracklist Collapse

Upcoming Events for Steely Dan

Nearly Dan Perform Steely Dan - 2025-03-09

Price Range: $Price not available
Location: Jazz Cafe, London

Steemy Dan - the Steely Dan Show - 2024-09-15

Price Range: $Price not available
Location: St Gregory’s Church, Suffolk

Steemy Dan - the Steely Dan Show - 2024-09-15

Price Range: $Price not available
Location: Jazz Cafe, London
0 0 votes
Article Rating
Subscribe
Notify of

0 Comments
Inline Feedbacks
View all comments

Stream My Old School on your favorite platform

Identify any song playing in your browser. Free.

Share My Old School Song Meaning with your friends

or discover new music

0
Would love your thoughts, please comment.x
()
x