Ruby Baby: Doo-Wop Through the Jazz Lens
The only cover on The Nightfly transforms a Leiber & Stoller classic into something stranger—the past reimagined by someone who lived through it differently.
The Drifters took “Ruby Baby” to number 10 in 1956. Dion brought it to number 2 in 1963. Donald Fagen’s 1982 version didn’t chart at all. This isn’t a failure of execution—it’s a difference in intent. Fagen wasn’t covering “Ruby Baby” to have a hit. He was examining it, the way an archaeologist examines a potsherd: carefully, with respect, trying to understand what it meant to the people who made it.
“Ruby Baby” is the only cover on The Nightfly, and its inclusion is deliberate. Leiber and Stoller’s song represented the exact era Fagen was trying to capture—the late 1950s and early 1960s, when doo-wop and R&B dominated AM radio and a Jewish kid in New Jersey could fall in love with Black American music through the barrier of his parents’ hi-fi.
The Arrangement as Commentary
The original versions of “Ruby Baby” were straightforward—verse-chorus structures with period-appropriate production, the vocal group harmonies stacked behind the lead. Fagen’s version retains the basic architecture but rebuilds everything inside it. The tempo is slightly slower. The groove is looser. The harmonies are jazzier.
This isn’t jazz-fusion showing off; it’s jazz as interpretive lens. When the horn section enters, they’re not playing the original chart. They’re playing something that could have been written by Thad Jones—tight voicings with chromatic movement, sophistication where the original had simplicity. The horns comment on the song rather than merely supporting it.
The effect is like watching a film colorized and then re-lit. The subject is the same, but the perspective has shifted. Fagen is showing us how “Ruby Baby” sounded in his head—filtered through years of jazz education and studio experience, transformed into something that remembers being simpler than it now is.
The Vocal Performance
Fagen’s voice was never suited for doo-wop. Where Dion brought operatic drama to the song and Bobby Day brought rhythmic precision, Fagen brings something closer to wry affection. He’s not trying to outperform the original vocalists. He’s trying to inhabit a younger version of himself who loved those vocalists.
The phrasing is more conversational than the originals. Fagen takes liberties with the rhythm, pushing and pulling against the beat in ways that would have been inappropriate on a 1956 single. This isn’t disrespect—it’s intimacy. He’s singing the song the way you sing a song alone in your room, not the way you sing it on American Bandstand.
The background vocals are handled by a professional session group, but they’re mixed further back than the originals would have placed them. The call-and-response that defined doo-wop becomes more like a conversation between past and present. Fagen’s lead is firmly in 1982; the backing vocals float somewhere in memory.
Production Values as Nostalgia
Roger Nichols’ digital recording captures “Ruby Baby” with a clarity that the original could never have achieved. Every nuance of the horn arrangement is audible. The bass guitar separates cleanly from the kick drum. The reverb on the snare is precise and controllable.
This production style creates an interesting tension with the material. The song is about teenage longing, the simplest and most universal of pop music themes. But the recording is sophisticated, expensive, deliberately adult. Fagen wasn’t making a nostalgia record in the sense of recreating the past. He was making a record about nostalgia—about the way memory transforms experience.
The drums deserve particular attention. Jeff Porcaro brings a different feel than Steve Jordan’s work elsewhere on the album. His playing acknowledges the song’s doo-wop origins while refusing to be constrained by them. The groove swings, but it swings in a way that Bobby Bland would have recognized rather than the stiff backbeat of early rock and roll.
The Cover as Self-Portrait
By including “Ruby Baby” on The Nightfly, Fagen was declaring his allegiances. This was the music that made him. Leiber and Stoller, working with Black artists to create songs that would cross over to white audiences, had essentially invented his musical vocabulary. The clever wordplay, the sexual subtext, the R&B foundation—these elements would resurface throughout Steely Dan’s catalog.
“Ruby Baby” in 1982 is Fagen’s way of showing his work. Here’s where I came from. Here’s what I heard on the radio when I was fourteen. Here’s the song I practiced in my bedroom, learning the moves that would eventually become something else.
The track doesn’t try to be definitive. It’s one interpretation among many, a snapshot of how one listener internalized a piece of pop culture. That’s all any of us ever have: our version of the music that shaped us, played back through everything we’ve learned since.