A nostalgic reflection on youthful rebellion and the complexities of college life.
Released in 1973 on their second album, Countdown to Ecstasy, “My Old School” peaked at number 63 on the Billboard Hot 100. While not a chart-topper in the traditional sense, its impact and enduring appeal far surpass its chart performance. It has become a staple of classic rock radio and a fan favorite, showcasing Steely Dan’s signature blend of intricate musicianship, sophisticated lyrics, and a touch of cynical wit.
The song’s genesis lies in Donald Fagen’s own experiences at Bard College in Annandale-on-Hudson, New York. In 1969, Fagen and his songwriting partner Walter Becker were caught up in a drug bust on campus. This incident, involving a large number of students and local law enforcement, left a lasting impression on Fagen. “My Old School” serves as a thinly veiled account of this event, with the lyrics painting a vivid picture of the anxieties and paranoia that permeated the atmosphere.
The opening lines, “I remember the thirty-five sweet goodbyes / When you put me on the Wolverine up to Annandale,” immediately establish a sense of departure and nostalgia. The Wolverine refers to the passenger train that ran from New York City to Annandale-on-Hudson, symbolizing Fagen’s journey to and from college. The “thirty-five sweet goodbyes” hint at the emotional weight of leaving home and venturing into the unknown.
The song’s narrative unfolds with a blend of specific details and veiled references. The line “It was still September when your daddy was quite surprised” suggests the disruption caused by the drug bust and the shock it sent through the community. The mention of “Kid Charlemagne,” a term often interpreted as a reference to a specific individual involved in the incident, adds a layer of intrigue and speculation.
Musically, “My Old School” is a masterclass in Steely Dan’s signature style. The song features a driving rhythm section, intricate guitar work (including contributions from Jeff “Skunk” Baxter), and Fagen’s distinctive vocals. The complex harmonies and sophisticated chord progressions create a sense of tension and unease, mirroring the lyrical themes.
Beyond the specific events that inspired it, “My Old School” resonates with a broader audience due to its exploration of universal themes. The song captures the anxieties of youth, the complexities of relationships, and the disillusionment that can come with confronting authority. It’s a poignant reflection on a specific time and place, but also a timeless commentary on the human experience. As we grow older, we often look back on our youth with a mix of fondness and regret. “My Old School” taps into this sentiment, reminding us of the formative experiences that shape who we become. It’s a song that invites us to reflect on our own “old schools,” the places and experiences that have left an indelible mark on our lives. It’s a song that with each listen, unfolds a new layer of meaning, a testament to the genius of Steely Dan. The track remains a quintessential example of their unique blend of rock, jazz, and pop, a testament to their enduring influence on music. It’s a nostalgic journey back to a time of youthful rebellion and the complexities of navigating the world as a young adult. The song’s legacy continues to resonate with listeners of all ages, proving its timeless quality and its place in the pantheon of classic rock.