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Frank Sinatra is an undoubted musical icon. He once offered the Fab Four a giant compliment when he spoke of George Harrison’s Abbey Road contribution, ‘Something’, calling it the “one of the best love songs written in 50 or 100 years.”

In fact, when Paul McCartney was growing up on the streets of 1950s Liverpool and just beginning his songwriting journey, he would dream of writing music for legendary crooners like Frank Sinatra: “Back then I wasn’t necessarily looking to be a rock ‘n’ roller,” Macca shared via The Beatles’ Anthology.

Looking back at the recording of one of the band’s masterpieces, and Paul McCartney’s personal favourite album, Sgt. Pepper’s Lonely Hearts Club Band, he said in Anthology: “There is a huge spectrum, from pop to serious blues players,” citing the wide range of influences and themes running not only throughout the band’s work but Paul’s own. “There were records other than rock ‘n’ roll that were important to me. And that would come out in the Beatles doing songs like ‘Till There Was You.’”

However, there was one song that Paul had written specifically with Sinatra in mind, and it was another of his previously constructed music hall ditties. “When I wrote ‘When I’m Sixty Four’ I thought I was writing a song for Sinatra,” he said. “I wrote [that] when I was sixteen — it was rather tongue-in-cheek — and I never forgot it.” Eight years later, McCartney picked the song back out of the pile and recorded it for the upcoming Beatles album.

The version heard on the record is almost exactly as McCartney had originally intended: “I wrote ‘When I’m Sixty Four’ vaguely thinking it would come in handy in a musical comedy or something,” he said. When you add in the conceptual notions of Sgt. Pepper, including the laugh track, it’s easy to see the connection. Prior to recording, Macca’s own father had just turned sixty-four, leaving many people to suggest that it instigated the song being selected for the album.

Sinatra would never sing ‘When I’m Sixty Four’ but would take on another of McCartney’s tunes, ‘Yesterday’, a cover which Paul counts among his favourites.

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