A Joyous and Poignant Time Capsule, a Sophisticated Homage to the Innocent Romance of the Golden Age of Rock and Roll.
By 1982, the dramatic and brilliant reign of Steely Dan had come to an end, leaving a gaping void in the landscape of intelligent rock music. From the silence emerged Donald Fagen, who immediately answered the doubts of the critical world with his debut solo album, The Nightfly. It was a cinematic triumph, a meticulously crafted, semi-autobiographical journey that became a critical and commercial success, peaking at number 11 on the Billboard 200. While the album was filled with new, highly sophisticated compositions, Fagen anchored his nostalgic trip with one poignant act of homage: a stunning reinterpretation of the classic “Ruby Baby.” Originally a hit for The Drifters in 1956 and penned by the legendary Jerry Leiber and Mike Stoller, Fagen’s version was released as a single, reaching number 58 on the Billboard Hot 100, its success a testament not just to the power of the original, but to the genius of its new arrangement.
The story behind “Ruby Baby” is a dramatic confrontation between the past and the present. The Nightfly is set firmly in the era of Fagen’s youth—the late 1950s and early 1960s—a world of atomic-age optimism, late-night jazz radio, and the birth of rock and roll. The inclusion of this song, a classic doo-wop track, is a deliberate, theatrical move. It serves as a musical time machine, representing the very music that would have poured out of the transistor radios of his suburban youth, fueling his early dreams of romance and rebellion. The drama lies in the tension between the original’s raw, four-piece simplicity and Fagen’s lush, high-tech re-envisioning. It’s an artistic statement: Fagen isn’t just covering a song; he’s taking a piece of his innocent past and examining it through the complex, cynical, yet still romantic, lens of his adult self.
Lyrically, “Ruby Baby” is a straightforward tale of teenage frustration: the narrator is utterly captivated by a beautiful, charismatic, and ultimately capricious girl who keeps him waiting and guessing. But in the context of The Nightfly, this tale of an irresistible woman becomes a powerful metaphor for the pure, uncritical romanticism of the era. It’s the sound of teenage desire, set to a score that is anything but juvenile. The music is where the real dramatic transformation occurs. Fagen replaces the raw doo-wop groove with a sophisticated, jazzy arrangement—the smooth, layered horn section, the intricate keyboard lines, and the precise, polished drumming are all signature Steely Dan production techniques. The backing vocals, paying direct tribute to the original vocal group sound, feel like a chorus of ghosts from the past, beautifully integrated into the adult Fagen’s sonic universe.
For those of us who grew up with the sounds of both the original rock and roll era and the subsequent sophistication of Steely Dan, “Ruby Baby” is a double dose of nostalgia. It’s a nostalgic echo of a time when the world seemed full of possibility, delivered with the kind of musical perfection only Donald Fagen could achieve. The song stands as a timeless and deeply emotional piece of music, a triumphant, yet melancholic, act of remembrance that perfectly fuses the innocence of the past with the genius of the present.