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Frank Sinatra’s “Softly, As I Leave You” Reviewed

Frank Sinatra’s genius wasn’t solely in his ability to make the greatest songs of the Great American songbook even greater, but also, though somewhat forgotten, in making the unbearably average and mundane, song after song, of syrup strings, and his very own movie soundtrack songs, second and third tier middle of the road songs from the scrap heap of life, sound like songs, something “Here’s To The Losers” isn’t. By the mid-1960s, by album # 33, Softly,  As I Leave You,  Frank was 50 years old and his voice was as strong as ever, but he was hopelessly out of step with modern pop, and as jazz was replaced by r&b and rock music, as the British Invasion wiped everything out of its path, Frank couldn’t quite nail down a great album when he needed it most. Softly, As I Leave You, was an outtake album plus three attempts to do something like what Bastille and Imagine Dragons did in the latter half of the 2010s: add beats to an established sounds. The songs aren’t good enough, it doesn’t work: it doesn’t go far enough, it isn’t daringly new, it is a slab of paint. After being caught by surprise by 50s rock, he was caught by surprise by the mob tops.

So why excavate a 55 year old album, just to say it isn’t very good? Because a man is the sum of his parts, and you can’t have 1965’s September Of My Years if you don’t go through the bad like Softly, As I Leave You and the ugly, America, I Hear You Singing. What is a pleasure, is noting how much work it took for Frank to build his catalog and how his pure skill of instilling soul into songs that to all intents and purposes has zero, remained for archaeologists to admire without enjoying. At the end of the album, he reaches a zenith of skill over song on no, not that one but Sammy Cahn and Jimmy Van Heusen’s “The Look Of Love,” reappropriating the end of “Witchcraft” and it sounds good but it is rotten. That’s Sinatra skill set. But even when Frank gets it, the back up singers, try “Emily,” destroy it. The best thing about the entire album is Sinatra’s sweet flow coda “I’ll tell you chum, it’s time to come come, blow your horn”.

He does this all album long with songs recorded over a two year period but warehoused, featuring six arrangers and conductors, including Nelson Riddle on five songs. All professional tinkle, tankle, barely swing orchestras who are simply session men doing what they can to add life to moribund orchestrations, constantly saved by Sinatra’s  bravado performances of songs that must have put him to sleep. Nothing stands out enough, certainly not the title track, and while the Neil Simon play (his first -two years on Broadway) made for a sparkling piece of Sinatra magic in the movie, “Come Blow Your Horn” deserves to be a great song, and it is the best attempt here, Sinatra decided not release it as a song (the movie was a huge hit in 1963), he chose “Soft, While I Leave You,” and watched it sink without a trace while in 1964 the Beatles released (in the US), Introducing… The Beatles, Meet The Beatles!, Twist And Shout, The Beatles’ Long Tall Sally, A Hard Day’s Night, Something New , and  Beatles for Sale. Sinatra may well have been (is) the greatest pop singer of all time, up there with Aretha Franklin and George Jones, but he got caught flat footed for the second time in his career. The Beatles, were half his age (Lennon was twenty-three during most of 1964), and they rolled him over just as they did the entire American songbook. Just as they did the entire country. It was The Beatles, I Hear You SInging, as the country recovered from extended mourning over the assassination of JFK.

Yet, as poorly conceived and executed in the modern age of Sinatra as possible, it plays as a holding action, and the songs where the drums come more to the forefront might not have worked but using r&b poopster Ernie Freeman certainly suggest Frank’s eyes were on the charts with “Softly, as I Leave You”, “Then Suddenly Love” and “Available”. But they don’t have the power of their convictions, it doesn’t go nearly far enough, and the album sunk on the incipient weakness of the material and Frank’s unwillingness to go get into bed with rock music. Presley figured out how to add pop to rock, but Sinatra couldn’t add rock to jazz. What you end up with is “Pass Me By” -a martial beat as cheerleader bop and a thing of stupendous horror, followed by the dramatic formation of the title track which sounds nothing like rock, actually it sounds nothing like anything

So why flog a dead album? Because in 2019, the Sinatra catalog is one big piece of  stupendous artistry and  with complete ease and a power almost arrogant in its completeness, wasn’t easy at all. Sometimes, Sinatra  couldn’t pull it off.

Grade: C






  1. Paul Quist on February 26, 2021 at 3:17 am

    Frankly, i do like the album. Very much, even. Of course, that is in retrospect. It may have been rather old fashioned when it came out, but it does sound great. And – yes, I know what some of you may think – I do even like the parts with the backing vocals. It’s sixties galore. An album I think deserves more credit. Some outstanding performances to enjoy.

  2. Alan Sanderson on November 6, 2021 at 10:15 am

    Sinatra at his worst was better than anyone else at their best. Case closed.

    • admin on November 6, 2021 at 10:54 am

      really? I guess you never heard his Bing Crosby album “America, I Sing Of Thee”…

  3. Charlie Mastro on November 21, 2021 at 8:43 pm

    Seriously though , your arguing with perfection . You lose !

  4. Paul Schrader on December 17, 2021 at 8:17 pm

    Sinatra did not sell out to rock. I like the album and the lead song. I play it often.

  5. paul graham on January 4, 2022 at 12:42 pm

    Francis Albert Sinatra was cool before rock n roll music was invented. He tried to modernised his
    music in 2000 with a disco version of “all but nothing at al” He did not do himself any favours by recording
    this mess. The original Jazz version is far superior than this. Frank Sinatra and his generation of musicians were among the best of any generation.

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