‘Scuse Me While I Disappear – Frank Sinatra sings “Angel Eyes”

I’d find it impossible to pick a single favourite Frank Sinatra performance, but this is one of them. It’s from 1958’s Only The Lonely, the beautiful black hole in Sinatra’s output. He made a fantastic group of “losers” records while inventing the concept album in the 1950s – In The Wee Small Hours, Where Are You?, No One Cares – but none evoke night, loneliness and lost love with such sustained focus, or such a balance of power and restraint.

The album was arranged by Sinatra’s greatest collaborator, Nelson Riddle, who was in a deep blue place while he worked: he’d suffered the deaths of his baby daughter and mother in rapid succession. Pain sometimes enters this music, along with sad beauty. By the time “Ebb Tide” begins, nine tracks in, the mood is so intense it resembles Bernard Herrmann’s music for Taxi Driver, except Herrmann wouldn’t write that for another two decades.

Sinatra, meanwhile, was going through his own grief, still failing to get over Ava Gardner, the lover who, the story goes, drove him to attempt suicide. What’s astonishing is, this was one of two albums Sinatra made in 1958, and the other was the swinging Come Fly With Me, the polar opposite – it’s hard to think of another artist bouncing between extremes like that, although Hitchcock did something similar that same year by somehow making Vertigo and North By Northwest back-to-back.

As “Angel Eyes” begins, there’s a glimpse of that other, top-of-the-world Sinatra, the guy at the party. But then it’s like he removes the mask and slips away into the night: the city is dark, he’s alone, he’s haunted, and he sounds like a large part of him doesn’t want it any other way. Riddle’s arrangement touches jazz, blues and pop, but it has a strange tempo, doesn’t so much swing, swagger or toddle as sweep, creep and prowl. Sinatra’s singing is incredible, hitting the real blue note. It gets more mysterious as it goes: the final five words are as good as any singing he ever did. It’s one of the greatest endings to any song ever recorded.

Written 2015 for a “pick your favourite Sinatra song” feature compiled by Glasgow City Music Tours to mark Sinatra’s centenary