
Paul McCartney’s favourite Frank Sinatra song: “I thought it was quite a good one”
It’s not always easy to see the influence of Frank Sinatra on Paul McCartney, but when you look deep enough, you can hear a semblance of his starry swing.
While Sinatra might not have been the biggest fan of The Beatles, calling them “kid swingers with mops of hair” and boldly predicting that they would never crack America in the early 1960s – don’t ask him to pick your lottery numbers – McCartney, on the other hand, always reflected in a rather complimentary manner when it came to the ‘Cycles’ singer.
In 2004, the bassist admitted to Uncut that his favourite song of Sinatra’s was ‘A Lovely Way To Spend An Evening’. It formed a selection of compositions the bassist pencilled as his “favourites”, a list that included Donovan, Fred Astaire and, strangely enough, George Harrison.
McCartney had rarely been known to praise Harrison’s writing during the guitarist’s lifetime, but the song, which features as part of his list, ‘Marwa Blues’, formed part of Brainwashed, Harrison’s swansong, and best-received album in a long time at that point. Interestingly, the song is instrumental, which might show that McCartney favoured Harrison’s melodies over his lyrics, but the song remained one of the guitarist’s most impressive works as a musician and a man.
Astaire’s ‘Cheek to Cheek’ is also interesting, because it explains McCartney’s fascination with whimsy, and the 1930s, particularly ballads ‘Honey Pie’ and ‘You Gave Me The Answer’. Indeed, McCartney namechecked Astaire during a live performance of ‘You Gave Me The Answer’, feeling that the tune was in keeping with his repertoire as a person and an artist.
But the inclusion of Sinatra’s tune is interesting because it’s hard to pinpoint the man’s influence on McCartney’s work in either The Beatles or in Wings, except to say that it fits somewhere between the aforementioned duo – capturing swinging melodies and a wink to go with it. But for a while, Macca seemed happy to rail against the type of music Sinatra signalled in the 1960s, instead creating more turbo-charged energy that was fuelled by the passion of stage rock.
McCartney rarely called Sinatra in his thousands of interviews, although he seemed miffed when the vocalist singled ‘Something’ out as his “favourite Lennon-McCartney song”. But McCartney was enamoured with Sinatra’s singing style and longed to write a song for him as a teenager. “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.”

As it happens, the ditty suited the more whimsical quality of Sgt. Peppers Lonely Hearts Club Band turned the band’s attention away from the rock riffs of the era to the more melodic factions of the 1920s and 1930s. The song, rich with character and piano noodles, was perfect for the album, and suited the more ambient textures better than the out-and-out rock of Revolver.
It’s hard to imagine Sinatra singing it as well as McCartney, as he wouldn’t have understood the references to English music hall or recognised the more cartoonish elements of the song. The bassist affects a helium-style vocal that likely stemmed from his interest in The Goons, although his younger brother Mike was the one who wore Peter Sellers’ influences more openly.
If anything, the song is more of a parody of Sinatra, as opposed to an out and out homage, so it’s interesting to hear that McCartney greatly admired “Old Blue Eyes”, and longed for him to sing his work.
Back to ‘A Lovely Way To Spend An Evening’: The song is rich in vocal harmonies and finds the vocalist singing almost entirely shorn of instrumentation. Sure, Sinatra’s backed by a collection of backing vocalists, but there’s nary a guitar nor a cello to carry him through the proceedings. Instead, his voice nests between a mosaic of soaring, shimmering voices, decorating the garden and lagoons that decorate the world in question. It’s a song entirely dedicated to the process of world-building, layering up into a snippet of joyful escapism.
Listening to the tune now, it sounds like the tender beginning of ‘Because’, a tune The Beatles recorded almost entirely without instrumentation. Harrison added some flourishes of synthesiser, but the intricate passages were performed by the vocalists, as Ringo Starr counted them in. Sinatra’s influence emerged in other ways over the years, and the former Beatle McCartney released ‘Frank Sinatra’s Party’ as part of the extras that formed part of Egypt Station.
Considering that the album had virtually no classics to speak of, the excellent ‘Frank Sinatra’s Party’ was a very curious omission, invoking the giddy invention of both his bands, especially the sophisticated sound paintings issued by Wings. But nobody has ever persuaded McCartney how to proceed with his career, and his work, rightly or wrongly, has always depended on how he feels at that moment in question. Somewhere within the realms of his musical fantasy came the sound of a songwriter saluting the presence of a master performer who had entered into his heart and soul in more ways than one.
Indeed, the bassist sent Sinatra a recording of his own to consider. “I once sent Frank Sinatra a song called ‘Suicide’,” McCartney recalled. “I thought it was quite a good one – but apparently he thought I was taking the mickey out of him and he rejected it.” Perhaps he should’ve looked up Sinatra’s prior critiques of The Beatles before even bothering.