It’s a Lonesome Old Town – Frank Sinatra

When Frank Sinatra signed to Capitol Records in 1953, he launched an artistic hot streak to which the only serious comparison in popular music since has been the Beatles’ career between 1963 and their dissolution in 1970. For the rest of the 1950s and into the 1960s, Sinatra alternately released collections of uptempo swing numbers and increasingly punishing albums of ballads, never mixing the two on the same LP. In so doing Sinatra, along with his producer Voyle Gilmore, arguably invented the concept album.

Frank Sinatra Sings for Only the Lonely may be the pick of these records, but it is also the bleakest. Sinatra had gone through a divorce from Ava Gardner, and arranger Nelson Riddle (a late substitute for the singer’s preferred choice of Gordon Jenkins) had just lost his mother and his daughter. The album Sinatra and Riddle made together in these unhappy times goes far beyond melancholy, achieving instead an eerie, exhilarating desolation.

The album was, as was Capitol custom at the time, recorded using two separate set-ups running simultaneously: eight orchestra mics for the mono recording and a three-mic ‘Decca Tree’ configuration for the stereo. There are audiophiles who claim the mono sounds better. To my ears, the stereo mix is musically superior because the lack of competition for aural real estate in the centre of the stereo picture gives Sinatra and his voice a bigger area to wander around disconsolately in, so to speak. As gorgeous as the orchestration is, nothing pulls you away from Sinatra’s performances. And what magnificent performances they are. Sinatra inhabits every line of the song, he explores every nuance of the lyrics, pulling the beat this way and that as he goes.

Riddle’s arrangements, meanwhile, with the dimensionality and wider soundstage afforded by stereo, range from enveloping warmth to disconcerting coldness (witness the uneasy-sounding ‘suicide’ strings that open the track, and their insinuating, spiralling recurrence at 2.08: they could have come straight from a Scott Walker record, or from a horror-movie score).

Sinatra’s phrasing was always at its most inimitable and deeply felt on ballads, particularly in the fifties, and he’s at the very top of his game on It’s a Lonesome Old Town. Notice how frequently he’s slightly in front of the beat, as if these painful admissions are coming out in little spurts he can’t quite control. This is not the ‘Fly me to… the moon’ Sinatra of a thousand tin-eared parodies. This is an artist of supreme technical facility letting go of all his little tricks and just singing the songs as he feels them.

Too unrelentingly dark to win the mass acceptance afforded to his swing albums, these records remain comparatively under-appreciated. Cuts such It’s a Lonesome Old Town are seldom played on the radio and often go unrepresented on compilations and retrospectives; the comparatively cutesy One for My Baby (cutesy being of course a relative term in this context) is the only song from Only the Lonely I’ve ever heard on daytime radio. But perhaps this is appropriate – no other records are as suited to late-night solo listening as Sinatra’s ballads albums. Small doses, though. They’re strong stuff


He’s Frank Sinatra and you’re not.

4 thoughts on “It’s a Lonesome Old Town – Frank Sinatra

  1. Ben Williams

    Hi Ross,
    Thanks for the brilliantly written, intelligent piece on Sinatra’s “It’s a Lonesome Old Town” – I have so enjoyed reading it. “Only The Lonely” is one of my two favourite Sinatra albums (the other one being “No One Cares”) – I keep on returning time and again to Sinatra in his melancholic mood – these songs touch me on a deep level, much more so than the “swinging” Frank – and these two albums are the cream of a really great Capitol crop for my money. The sound of “It’s a Lonesome Old Town” is bleak but beautiful. This is Sinatra’s “noir” sound (the film critic David Thomson wrote that Sinatra’s is a noir voice – I love that) – it seems to conjure up images of deserted city streets at night and cigarette smoke in the lamplight. I thank you again for writing such an insightful blog.
    With appreciation and best regards,

    1. rossjpalmer Post author

      Thanks for your very kind words! I’m so glad you enjoyed it, and I’m with you entirely – there’s performances and songs and arrangements all over Sinatra’s swing records that I love, but it’s the ballad albums that I always come back to.
      I just looked up that quote of David Thomson’s that you mentioned and found it in an obituary – do you know whether it was an extract from a longer piece or just a quote he gave in response to Sinatra’s death? I’d love to read more of his thoughts if possible.
      Thanks again Ben.


      1. Ben Williams

        Hey Ross,
        That quote is from David Thomson’s excellent & essential “New Biographical Dictionary of Film.” It’s in the 2003 edition – but I expect it is also in later editions. The exact quote is as follows: “He glamorised the fatalistic outsider; he made his own anger intriguing; and in the late fifties, especially, he was one of our darkest male icons. It helps illustrate the interaction of singing and acting. Sinatra is a noir sound, like saxophones, foghorns, gunfire, and the quiet weeping of women in the background.”
        Isn’t that a great sentence? Thomson manages to put into words exactly how I feel when I hear these wonderful Sinatra ballads. The synergy created by Sinatra and Nelson Riddle on the “Only The Lonely” album is sublime.
        Best to you,

      2. rossjpalmer Post author


        It’s great! Thanks for digging it out for me. I’ll be looking for a copy of that book now!

        Thanks again for your very kind comments. Take care,


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