In the past several weeks I’ve gone down a rabbit hole trying to figure out the meaning of “My Old School.” Even though songwriters Donald Fagen and Walter Becker have never revealed much about their semi-autobiographical lyrics, many of the facts about the song have been nailed down. Still, some of the lyrics remain notoriously obscure, and we may never know their original intended meanings. I’ll try to lay out the known facts and offer my best theories about the parts that have remained unclear.
My comments are based on various Wikipedia articles, the Entertainment Weekly article mentioned in another post, contemporary newspaper accounts, and numerous other articles online. The EW article includes a particularly helpful interview with Fagen in which he talks about the events in the 1st verse of the song.
“My Old School” tells the story of Donald Fagen and his girlfriend getting into trouble with the law in 1969 when she visited him during his senior year at Bard College. At least that’s the main storyline. Fagen and Becker had met at Bard in 1967 when Fagen was a junior and Becker was a freshman. They quickly developed a close relationship and began collaborating musically. In a 1985 interview in The Bard Observer, Fagen was asked about “My Old School.” He described the song as “a personal story combining different experiences we both had at Bard. Also there were some fantasy sequences in there as well.” I believe this answer is the key to interpreting the lyrics.
Perhaps the biggest mystery about this song is why the lyrics alternate between addressing the girlfriend directly in the second person (“you/your”) and referring to her indirectly in the third person (“she/her/the girl”). Some have speculated that the third person references are about a female administrator at Bard or even about the college itself. But I couldn’t find any solid evidence for these interpretations...and they don’t actually fit the lyrics.
It’s a little complicated, but figuring out what’s going on with the pronouns is essential to understanding the lyrics. It turns out that the alternating pronouns divide the song into two distinct sections. All of the second person references (“you/your”) are in the 1st and 3rd verses, which I’ll call section A. And all but two of the third person references (“she/her/the girl”) are in the chorus and the 2nd verse, which I’ll call section B.
We know from interviews with Fagen and from newspaper accounts that the lyrics in section A are very likely about his long-term girlfriend, Dorothy White. So it would be reasonable to assume that section B is where the “fantasy sequences” and Becker’s experiences are located. The lyrics in section B suggest that Becker had some kind of girlfriend problem while he was at Bard. The third person references in this section may have been a way to differentiate Becker’s angry feelings of betrayal from the romantic feelings Fagen expresses about his girlfriend in section A. But the bottom line is that, as Fagen implied in his interview, the song is probably a mashup of two separate storylines.
My line-by-line comments are in square brackets below. My personal theories are designated with ^.
SECTION A: VERSE 1
This verse is about a drug raid that happened when Fagen and Becker were students at Bard. Fagen is the narrator, and he directly addresses his girlfriend using “you” or “your.”
I remember the thirty-five sweet goodbyes [despite all the speculation about 35 being half of 69 if you round up, a simpler explanation is that “goodbyes” refers to kisses^]
When you [Dorothy White, Fagen’s girlfriend from no later than 1969 until at least 1975, two years after the song was released; some sources say she was his high school sweetheart; she painted the cover for the “Countdown to Ecstasy” album and took the cover photograph for the “Katy Lied” album] put me on the Wolverine [a passenger train that in the 1960s ran from New York City to Chicago via Detroit; since Fagen’s family lived in South Brunswick, New Jersey, he likely would have boarded the train at Grand Central Station in Manhattan] up to Annandale [Annandale-on-the-Hudson, a hamlet in southeast New York state, where Bard College is located; one of the Wolverine stops was near Annandale]
It was still September
When your daddy was quite surprised
To find you with the working girls [prostitutes]
In the county jail [in May 1969 — here changed to September — Dorothy White visited Fagen at Bard a few weeks before his graduation; while she was there, she, Fagen, Walter Becker, and other students were arrested during a drug raid, according to local newspaper accounts; the raid was organized by the local district attorney’s office with the rumored cooperation of the college administration; Bard officials bailed out all of the 44 students who were arrested, including Fagen and Becker, but not White, who wasn’t a student; the charges against Fagen and Becker were eventually dropped]
I was smoking [pot] with the boys upstairs [around 4-5 AM in his off-campus residence]
When I heard about the whole affair [the drug raid; sheriff’s deputies had descended on the Bard dorms and off-campus student residences and were making arrests]
I said oh no
William and Mary won’t do [maybe he was worried he might get kicked out of Bard, but transferring to William and Mary in Virginia, wasn’t an option^; some have argued that Bard was known as “the William and Mary of the north,” but I couldn’t find any solid evidence to support that idea; also consider that Bard is a small, private, liberal arts college in contrast to William and Mary, which is a public university and one of the eight public Ivy League schools]
SECTION B: CHORUS AND VERSE 2
Apart from the iconic refrain,“I’m never going back to my old school,” section B likely contains a mix of “fantasy sequences” (fictional storylines) and Walter Becker’s account of his bad experiences with an old girlfriend.^ In this section the girlfriend is consistently referred to as “she,” “her,” or “the girl.”
Well, I did not think the girl
Could be so cruel [it’s likely that this line is about one of Becker’s ex-girlfriends rather than Dorothy White — after all, songwriters don’t typically write revenge songs about their current girlfriends^; some have speculated that White cooperated with the police and gave them information about Fagen’s marijuana use, but available interviews and contemporary newspaper accounts don’t support this argument]
And I’m never going back
To my old school [the narrator is so angry at Bard officials for their supposed complicity in the drug raid that after leaving Bard, he vows to never go back]
Oleanders growing outside her door [probably a metaphor for marijuana growing in Becker’s ex-girlfriend’s backyard^; songwriters in the 1970s had to make veiled references to marijuana; otherwise their songs wouldn’t have gotten much radio play; “oleanders” might not be the perfect metaphor; but it does fit the rhythm and the melody; it’s also one of the most memorable and most singable words in the song, similar to “I remember” and “California”]
Soon they’re gonna be in bloom
Up in Annandale [Becker is also growing marijuana at his off-campus residence; “up in Annandale” suggests that his ex-girlfriend wasn’t enrolled at Bard^; she may have lived in New York City where he went to high school^]
I [Becker^] can’t stand her [his ex-girlfriend^]
Doing what she did before
Living like a gypsy queen
In a fairy tale [this phrase paints a picture of someone living a nomadic, nonconformist, perhaps reckless lifestyle^]
Well, I hear the [Wolverine train^] whistle but I can’t go
I’m gonna take her down to Mexico
She said oh no
Guadalajara won’t do [this may be a “fantasy sequence”^; the narrator had initially hoped to take his girlfriend by train to Mexico, possibly to avoid prosecution, but she refused to go with him^]
SECTION A: VERSE 3
This verse circles back to the drug raid from verse 1. We are back to Fagen as the narrator, and again he uses “you” to refer to his girlfriend.
California tumbles into the sea
That’ll be the day I go
Back to Annandale [Fagen did eventually go back to Bard in 1985 to receive an honorary doctorate]
Tried to warn you
About Chino [this one is tough to pin down; “Chino” is the Spanish-language term for people of Chinese ancestry, so this might have been a Chinese-American law enforcement officer with that nickname^; or it might have been a detective who liked to wear chinos slacks^] and Daddy Gee [before the drug raid Fagen had tried to warn Dorothy White about Chino and local assistant district attorney, G. Gordon Liddy, in his pre-Watergate days; Liddy had a reputation for being strict on drugs]
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 [these are the only occurrences of “her” and “she” in section A, which might seem odd at first; but Fagen and Becker are just repeating a refrain from section B]
In the past several weeks I’ve gone down a rabbit hole trying to figure out the meaning of “My Old School.” Even though songwriters Donald Fagen and Walter Becker have never revealed much about their semi-autobiographical lyrics, many of the facts about the song have been nailed down. Still, some of the lyrics remain notoriously obscure, and we may never know their original intended meanings. I’ll try to lay out the known facts and offer my best theories about the parts that have remained unclear.
My comments are based on various Wikipedia articles, the Entertainment Weekly article mentioned in another post, contemporary newspaper accounts, and numerous other articles online. The EW article includes a particularly helpful interview with Fagen in which he talks about the events in the 1st verse of the song.
“My Old School” tells the story of Donald Fagen and his girlfriend getting into trouble with the law in 1969 when she visited him during his senior year at Bard College. At least that’s the main storyline. Fagen and Becker had met at Bard in 1967 when Fagen was a junior and Becker was a freshman. They quickly developed a close relationship and began collaborating musically. In a 1985 interview in The Bard Observer, Fagen was asked about “My Old School.” He described the song as “a personal story combining different experiences we both had at Bard. Also there were some fantasy sequences in there as well.” I believe this answer is the key to interpreting the lyrics.
Perhaps the biggest mystery about this song is why the lyrics alternate between addressing the girlfriend directly in the second person (“you/your”) and referring to her indirectly in the third person (“she/her/the girl”). Some have speculated that the third person references are about a female administrator at Bard or even about the college itself. But I couldn’t find any solid evidence for these interpretations...and they don’t actually fit the lyrics.
It’s a little complicated, but figuring out what’s going on with the pronouns is essential to understanding the lyrics. It turns out that the alternating pronouns divide the song into two distinct sections. All of the second person references (“you/your”) are in the 1st and 3rd verses, which I’ll call section A. And all but two of the third person references (“she/her/the girl”) are in the chorus and the 2nd verse, which I’ll call section B.
We know from interviews with Fagen and from newspaper accounts that the lyrics in section A are very likely about his long-term girlfriend, Dorothy White. So it would be reasonable to assume that section B is where the “fantasy sequences” and Becker’s experiences are located. The lyrics in section B suggest that Becker had some kind of girlfriend problem while he was at Bard. The third person references in this section may have been a way to differentiate Becker’s angry feelings of betrayal from the romantic feelings Fagen expresses about his girlfriend in section A. But the bottom line is that, as Fagen implied in his interview, the song is probably a mashup of two separate storylines.
My line-by-line comments are in square brackets below. My personal theories are designated with ^.
^My theories
[Edit: Minor edits]