Bob Dylan’s foray into recording standards from the Great American Songbook, beginning in 2015, marked a surprising turn for an artist once known for a vocal style famously likened to a distressed animal. This shift placed him in unexpected proximity to the crooning elegance of Frank Sinatra, a titan of the Great American Songbook. While Sinatra’s sound was polished and orchestrated, Dylan’s was raw, characterized by gritty guitar work, a piercing harmonica, and an embrace of imperfection. Sinatra helped formalize the Great American Songbook, a cornerstone of American popular music that shaped public taste before the rise of rock and pop. In contrast, Dylan, a champion songwriter of the rock era, primarily performed his own compositions, diverging from the lyrical traditions of Gershwin and Porter.
Their artistic sensibilities also represented different eras and values. Sinatra embodied style, swagger, and vulnerability, appealing to a generation of young adults returning from war, seeking music that evolved with their adult experiences of love and loss. Dylan, on the other hand, resonated with the earnest folk music enthusiasts of the early Baby Boom generation, embodying prophecy, autonomy, and mystery. He was seen as a visionary and incorruptible figure, a perception rooted in his unwavering dedication to his musical craft rather than political stances.
It’s a curious evolution that Dylan, whose music was once seen as a rejection of the pre-rock era’s popular songs, now performs these very standards, including their “corny words.” This immersion in the music of his parents’ generation coincided with his Nobel Prize in Literature win, a landmark event that highlighted his profound gift for bringing words to life not through vocal power, but through masterful inflection. As one singer noted, “He conveys so much, and I’m not sure how.”
Dylan’s albums Shadows in the Night (2015), Fallen Angels (2016), and the three-disc Triplicate (2017) offer insights into this “how.” His voice, in remarkable form, delivers vibrant reinterpretations rather than mere nostalgic tributes, breathing new life into songs from a bygone era.
Sinatra was renowned for his meticulous attention to lyrics, often reading them aloud before recording to find his emotional connection. His 1957 recording of “I’m a Fool to Want You,” widely seen as a lament for his ex-wife Ava Gardner, showcases this. Sinatra’s tormented delivery, particularly his drawn-out “said” in the bridge, emphasizes his powerlessness. Gordon Jenkins’s cinematic arrangement amplifies the song’s emotional weight, creating a powerhouse performance.
In contrast, Dylan’s rendition of the same song begins with a near growl. While a direct vocal comparison might seem uneven, Dylan demonstrates his unique interpretative skills. Like Sinatra, he imbues the bridge with intensity, but he employs a broader range of inflections, emphasizing certain words like “time” and “need” with subtle variations in each performance.
While Sinatra’s recordings span decades with varying arrangements and orchestras, Dylan’s were recorded over a shorter period with a consistent band. This consistency often makes his interpretations more cohesive, especially when compared to some of Sinatra’s earlier, less-defined recordings. Furthermore, Dylan’s “lived-in” voice, marked by time and experience, conveys a depth of emotion that Sinatra’s smoother instrument doesn’t always capture.
Dylan’s personal investment in certain songs is also evident. Sinatra’s rendition of “Why Try to Change Me Now” can feel detached, but Dylan imbues it with a personal stamp, relishing lyrics like “I’ve got some habits even I can’t explain.” His subtle pause before the key phrase “Why can’t I be more conventional?” adds a winking self-awareness to his lifelong defiance of convention.
Sinatra’s technical precision, while impressive, can sometimes feel dated. In “What’ll I Do,” his clear enunciation, particularly of “photograph,” distances the listener. Dylan’s more informal delivery, however, creates intimacy. His tender rendition of the song expands its emotional scope, allowing for a wider interpretation of loss.
Paradoxically, Dylan sometimes inverts lyrical meanings, as heard in “The Night We Called It a Day.” While Sinatra and others contrast the owl’s mournful song with the narrator’s own sadness, Dylan’s altered phrasing, “No bluer than he was I,” obscures this contrast, leading to interpretations of confusion or deliberate artistic ambiguity.
On Triplicate, Dylan’s interpretations of Sinatra classics like “The September of My Years” and “Stormy Weather” are particularly compelling when juxtaposed with the originals. “Once Upon a Time,” a standout from Sinatra’s September of My Years album, features Sinatra’s rich voice and elegiac string arrangements. In 1965, as Sinatra turned 50, these lyrics likely evoked a generation’s reflections on youth, war, and changing times. Dylan, in his mid-seventies, delivers the song’s melancholic payoff, “Once upon a time never comes again,” with a ragged voice striving for gentleness, the effort itself becoming a key element of his emotional impact.
Dylan has become a custodian of American folk, blues, and country music, favoring what he calls archaic forms. However, in his recordings of Sinatra standards, he is not a revivalist but a modernizer. Eschewing the orchestral arrangements of Sinatra’s era, Dylan opts for a small-group combo, with acoustic guitar, bass, and drums forming the core. His arrangements achieve an extraordinary intimacy, enhanced by close-miked vocals that capture his every breath. While Sinatra’s accompaniments by masters like Nelson Riddle and Gordon Jenkins were superb, they could sometimes overshadow the singer’s emotional delivery.
The stylistic divergence between Sinatra’s lush orchestrations and Dylan’s sparser arrangements reflects a broader cultural shift over the past half-century, favoring roughness over polish, vernacular over formality, and suggestion over directness. Dylan’s versions of early Sinatra tunes like “Melancholy Mood” and “On a Little Street in Singapore,” originally recorded with dominant big bands, are striking in their reinterpretation. Dylan’s band delves into the songs’ melodies, using the rhythm section to great effect, savoring each vocal line. Dylan’s rendition of “Melancholy Mood,” beginning with a bluesy guitar intro, builds narrative tension before he delivers the lyrics with compressed emotional power.
Dylan’s band deserves significant credit for the success of this ambitious project, particularly in their ability to match Sinatra’s swinging style, a more challenging feat than interpreting ballads. While “The Best Is Yet to Come” might not win over non-Dylan fans due to his gravelly tones, his performances of lighter songs like “I Guess I’ll Have to Change My Plans” and “Braggin'” are guilty pleasures, showcasing his ability to inject personality and humor into unexpected material.
For some, Dylan’s voice remains an acquired taste. However, his compelling vocalizations breathe new life into these standards, and his arrangements offer a contemporary sound. He isn’t merely “covering” these songs; as he puts it, he is “uncovering them,” bringing them “out of the grave and bringing them into the light of day.” Ultimately, whether one prefers Dylan’s or Sinatra’s interpretation may simply come down to personal preference. As Dylan himself stated, “It’s all music, no more, no less,” a sentiment beautifully realized in these recordings.
Paul Beston is managing editor of City Journal and author of The Boxing Kings.