My regular readers may have heard me talk of the life transition that lead to me discovering the Great American Songbook and the music of Frank Sinatra. I knew so little about this music that I had no idea what to buy. I owned Harry Connick’s music and Frank’s The Reprise Years compilation on cassette but that’s about it.

I must confess; I wasn’t always as law-abiding as I am now. I wasn’t always the respecter of libraries that I am now. Back around this time, I borrowed from my public library a Frank Sinatra cassette. I may take it back one day. Again, I had no understanding of this tape or the music on it. Some time later I discovered that what I had was one tape of a 1986 multi-tape box set called The Voice: The Columbia Years 1943-1952. One side of my tape – pictured below, left – was Sinatra Standards and one was Sinatra Swings.

I guess, then, what I’m “suggesting” on this inaugural segment of this new series is this box set or one like it. There’s also a newer version with almost the exact same title – minus “The Voice” – and I’ve also seen this one on the right which is the complete Columbia recordings.

This for me is a fascinating and unique part of Sinatra’s recording career. For collectors who want to own something from each era of Frank, I feel it’s essential to own at least some of his work with Tommy Dorsey. This is chronologically a good place to start and also Dorsey and his outfit provide – along with Glenn Miller? – perhaps the finest example of big band music. Add Francis to the mix and the music is even better. But then, famously, historically, Frank left Tommy and struck out on his own which, believe it or not, was a daring move at the time as the music industry was being lead by the big bands; performing solo was the risky exception. As many of you know, Frank recorded as a solo for Columbia from 1942 until he went to Capitol Records in 1953 and basically changed the music industry. Many will also know that this Columbia period was his least successful and it was also during this era that Sinatra hit rock bottom.

So, Frank’s big band work with Dorsey is delightful and his Capitol work is nothing less than historic but in between are these Columbia sides. That alone for me makes them interesting for many reasons not the least of which is that they are lesser known. My suggestion for this opening episode of Suggesting Sinatra is basically a playlist; the Standards/Swings cassette I’ve owned for years. The tape eventually crapped out on me so I found the songs among my Frank collection and built the playlist. I was missing several tracks and had to buy the mP3s; that above-mentioned Complete Columbia set used to be on iTunes. That set didn’t have the master take of “Mean to Me” so I had to dig and found it on one of iTunes’ own Sinatra playlists, an “album” they call 101 Hits.

There is some intangible quality to these songs. I often talk about something that is “unencumbered by greatness”. You may love Citizen Kane but perhaps it has been analyzed and praised so much that you may find it hard to sit and enjoy it as cinema, as if you didn’t know anything about it and as if you were watching it for the first time. Sometimes when I listen to Frank’s landmark 1955 recording of “I’ve Got You Under My Skin” – my second favourite Frank song – I will get lost in what I’ve read about Nelson Riddle’s arrangement or Milt Bernhart’s trombone solo or the song’s place in the pantheon and I forget to just sit back and enjoy it. Well, most of Frank’s Columbia work is wonderful, yes, but – aside from a few tracks – they are not considered his best songs. It can be nice, then, to sit back and listen to Sinatra songs you’re maybe not too familiar with or haven’t heard before. It’s nice to just sit back and hear him sing – before he had control of the whole world. These songs transport me right back to some long-forgotten sitting room. The travails of the day have been put aside. You finally sink back into your favourite chair and carefully stuff tobacco into your pipe (totally harmless in this scenario). You light it and sit back with a sigh. You take comfort from the presence of your significant other sitting in her favourite chair, perhaps reading a recently-delivered letter or the remains of the newspaper. You work the dials on your Philco and – after it warms up – out flows The Voice.

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Make no mistake; each song on this playlist is a delight, making these songs a great place to start sampling Sinatra’s solo output for Columbia. I always thought it strange that the Standards side of the tape starts off with the blasting brass of “Saturday Night” and then settles down and mellows out the rest of the way. “Poinciana” is my fourth favourite Sinatra song. It has a wonderful exotic charm featuring gorgeous strings. “Close to You” was introduced by Frank in ’43 and is presented here a cappella. He would record the song again for Capitol when it served as the title track for his 1957 album. Many fans know “I’m a Fool to Want You”. An early Sinatra masterpiece, Frank is credited as co-writer as he changed certain lyrics to reflect his torment over Ava Gardner. It is an emotional torrent and legend has it that Frank recorded it in one take and then bolted from the studio. He revisited “I’m a Fool to Want You” for 1957’s Where Are You? but the original – recorded with the Ray Conniff Singers – is an open wound. Great way to end Side One of my cassette.

“Should I?” is a buoyant song that appeared on an early album from FS released in 1950, Sing and Dance with Frank Sinatra. “Mean to Me” was the tune I had trouble finding but it is certainly worth searching for. Frank employs some scatting on “It All Depends on You” and “Deep Night” and “Castle Rock” are two standouts. In 1951, Columbia’s much-maligned A&R man, Mitch Miller, re-teamed Frank with his old boss, Harry James. James is often considered the greatest trumpeter of the big band era and he makes stunning contributions to these two tracks. “Deep Night” is cushioned in a dramatic tone and Harry’s riffs are fiery blasts. James later said that “Castle Rock” was “the worst thing that either of us ever recorded” but I beg to differ. It bristles with energy and Ray Conniff’s arrangement is delightfully brisk. An interesting, somewhat personal side note to this track is Frank’s spoken exhortation to Harry before one of James’ solos; “Go get ’em, Harry – for old times sake!” When I first listened to this cassette, I had no idea who Harry James was or that Frank and he were working together again after 12 years apart. The first person I thought of was Harry Connick, Jr., who had a rep at the time of being a throwback and a Sinatra-type crooner. So when I heard Frank encouraging “Harry”, I got chills; is Frank somehow speaking to Connick from out of the mists of time?! 

1947’s “Sweet Lorraine” showcases Sinatra in pure jazz form and teams him with a stellar backing group of jazz players; staggering to consider that, at this early juncture, Nat Cole is supporting Frank Sinatra on piano. “You Can Take My Word For It, Baby” is my fifth favourite Frank Sinatra song. He recorded this in 1947 with the Page Cavanaugh Trio, a jazz group that appeared in two Doris Day films. By the way, is “Page Cavanaugh” not the coolest name ever? This tune and others from this time that Frank recorded with small groups were and are today considered second tier to the songs he was crafting with arranger Axel Stordahl and full orchestra. I have read that Frank cared little for these throwaways but the result may be that this frees him to loosen up and have fun and what remains are relaxed, carefree and charming performances. For me, “You Can Take My Word For It, Baby” is an absolute delight and its rarity makes it all the more appealing. Searching the internet for info on this song is futile and this seems to add to its appeal. As I said earlier, this is not Frank Sinatra, The Chairman of the Board. This is just Francis cutting loose with a small group.

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Do yourself a favour and check out this lovely era of Frank Sinatra. I present these songs as a playlist and they are a wonderful place to start. But don’t take my word for it, baby, seek out the solo Columbia sides for yourself and discover what you like. I think you’ll be glad you did. See ya next time for another installment of Suggesting Sinatra.

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• Saturday Night (Is the Loneliest Night in the Week)
• Poinciana
• Try a Little Tenderness
• Autumn in New York
• April in Paris
• Dream
• Nancy (With the Laughing Face)
• Put Your Dreams Away
• I’m Glad There Is You
• Day by Day
• Close to You
• I’m a Fool to Want You
• Should I?
• Birth of the Blues
• Mean to Me
• It All Depends on You
• Deep Night
• Sweet Lorraine
• Castle Rock
• Why Can’t You Behave?
• My Blue Heaven
• S’posin’
• You Can Take My Word for It, Baby
• Blue Skies