The most surprising thing about Bob Dylan choosing to release a song made famous by Frank Sinatra – Full Moon and Empty Arms – as the first track from his new album, is that anyone might be surprised. After all, it's not like his Theme Time Radio Hour showed a man with rigid tastes (and the very first episode, broadcast on 3 May 2006, featured Sinatra's 1966 recording of Summer Wind). His 2009 album Christmas in the Heart saw him addressing seasonal standards, among them – unavoidably, given they were standards – songs previously performed by Sinatra. And, most saliently, in 1995 Dylan performed at Sinatra's 80th birthday gala, singing – apparently at the great man's request – Restless Farewell, from his 1962 debut album The Times They Are a-Changin'.
On the face of it, Dylan and Sinatra might appear united by little more than nationality, longevity and profession. And the faultlines between them – generational, political, stylistic – would seem to be insuperable. But really, they hold many things in common, not least the fact that Sinatra – more than Elvis, even – defined the role of the modern pop singer. And then – as much as Dylan, perhaps, and certainly before Dylan – set the template for the pop star who reinvents himself.
Sinatra's reinventions were not the movement from character to character, à la Bowie, but the redefining of himself in relation to his audience, to the music business, and to changing times – a trait very much shared by Dylan. Full Moon and Empty Arms comes towards the end of Sinatra's first flush of stardom. Through the second world war he had become a huge star at home, the hero of the bobbysoxers, but generating commensurate enmity among an adult male audience. While the "greatest generation" was overseas, fighting, Sinatra – who was exempted from military service for health reasons – was at home being screamed at, making money.
As the 40s faded into the 50s, his career ebbed, to be revived in 1953 by two things: the Oscar he won for his role in From Here to Eternity, and his signing to Capitol Records. At Capitol he reinvented himself as an adult singer of adult songs, no longer a teen idol. More to the point, he was one of the pioneers of the very thing that made possible the great rock boom of the 60s: the fully realised, thematically united album.
Before 12in vinyl, the album had been what its name suggests – an album of separate 78rpm discs, a mini box-set of sorts. Columbia introduced the 12in, 33rpm vinyl album in 1948, and when he signed to Capitol, Sinatra saw its possibilities and exploited to them to the full, notably on his second and third records for the label – 1955's In the Wee Small Hours (the classic of heartbreak balladry) and the following year's Songs for Swingin' Lovers (the disc that best encapsulates the public perception of Sinatra, musically). These were not the discs of two singles plus 10 pieces of filler that were the norm in rock music, something that did not change until the early- and mid-60s, when the Beatles and Dylan began to think of albums as artworks in their own right.
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The second great Sinatra reinvention was one that would be crucial to rock's status, by treating musicians as artists rather than fodder for the labels. In 1960, he established his own label, Reprise, with the specific aim of gaining more artistic control not just for himself, but for the musicians who joined the label. He sold the label to Warner Bros by 1963, but had taken the first steps to establishing the artist as the driver of the relationship with the label, albeit that could only happen if the artist was commercially powerful in their own right.
What also unites Sinatra and Dylan is artistry: especially a fierce desire to do what they wanted, even if that has sometimes (often, in Sinatra's case) resulted in missteps. Dylan recorded Christian albums; Sinatra embraced bossa nova. Dylan took a left turn away from the "wild, thin mercury sound" and turned to roots; Sinatra, in the same year he released My Way (1969), the Sinatra cliche of Sinatra cliches, he also put out Watertown, a rock-influenced song cycle about a middle-aged man left alone with his kids after his wife has walked out, composed by Bob Gaudio – who worked on hits for the Four Seasons – and lyricist Jake Holmes, best known for Dazed and Confused, which would be lifted by Led Zeppelin. Just as Dylan was not just a folk singer, so Sinatra was not just a crooner. His best recordings combine an irresistible arrogance with a distinct vulnerability – for all that his public persona was fairly revolting, the voice on the records communicates a startling humanity and appreciation for people's foibles. He speaks to people, just like Dylan. He is not just a sharp suit and a glass of whiskey.
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But, perhaps, what unites the pair most strongly is their position they share as totems of American popular music in the 20th century. Between them they created templates that are still seen as definitive. Not for nothing do TV talent shows have Rat Pack weeks, or young rock singers try to capture Dylan's adenoidal mid-60s cool – even if their talents are impossible to replicate. American music is unimaginable without either of them. Looked at that way, Dylan covering Sinatra is as natural as breathing.
Of course, perhaps he just liked the song.