There was only ever going to be one path for Frank Sinatra. While he enjoyed tremendous success with the Tommy Dorsey Orchestra, Frank was single-minded enough to feel the need to go it alone. Trouble was, singers simply didn’t do that in 1942. As I’ve said before, the comfortable place for a singer to be in this era was as part of a big band. Solo singers, while not unheard of (Al Jolson), were certainly not the norm. Sinatra informed Dorsey he was leaving. Dorsey reportedly said “I hope you fall on your ass”. There is lots of interesting ‘story’ to their parting which you should look up and read. Sinatra took his Dorsey arranger, Axel Stordahl, with him and began making his own records for Columbia.

The years 1943-1952 warrant their own story as these years are a unique mini-era in Sinatra’s career. The Columbia sides are an origin story of sorts for me. In the early ’90’s, as I was just beginning to discover jazz and traditional pop, I really had no clue what artists to look for. I wasn’t even really sure what it was I was after: jazz, pop vocals, funk, lounge. All I knew was that something else was going on in the ’50’s besides Elvis Presley and Little Richard. And I knew who Sinatra was. The first music I owned as I began to ‘look elsewhere’ was Harry Connick, Jr.’s Star Turtle album (New Orleans funk), the soundtrack to the Clint Eastwood film on Thelonious Monk, Straight, No Chaser (jazz) and a cassette that made up half of a box set devoted to Frank’s Columbia-era recordings. Subsequently, I knew and loved some of these lesser known recordings before I knew the more popular Capitol songs of the 1950’s.

The reason this era is often overlooked is because, almost from the moment he went out on his own, Frank Sinatra’s career went into a general decline. The material and Frank’s ability to deliver were both at their lowest point. It’s hard to believe but, for myriad reasons that you should look up and explore, for a time in the early ’50’s it looked as if Frank was just a flash in the pan. A singer who flamed brightly with a popular big band but one that couldn’t sustain his momentum as a single. Also, in this era of high moral standards, Sinatra’s personal life was in turmoil. He had left his wife, Nancy, and was in a tumultuous relationship with one of the most beautiful and popular actresses of the time, Ava Gardner. At this time in history, such a lifestyle could be very damaging to a career as the public demanded a certain decorum from its stars. Frank’s stormy relationship with Ava had its effect on his talent and his judgement. This was also the time of the ‘novelty’ song; screwy songs with hokey lyrics about inane subjects. While Frank did descend into madness with the recording of the infamous “Mama Will Bark”, he was generally incapable of ‘dumbing down’ his aspirations to be the best and he found there was little room and a lesser acceptance of high quality vocalizing. Also though, the sound emanating from his throat was certainly not what it used to be. Amidst all this tumult, Frank persisted but, after some strong years in the mid-1940’s, he found his popularity – and his craft – was waning.

If you explore the recordings he made in this era, however, you will find another segment of Sinatra’s career that brings immense pleasure and warm feelings. Similar to his big band recordings, the Columbia sides make for wonderful living room/rocking chair listening. It’s an era often overlooked due to Sinatra’s general decline but, while the recordings may not stand up under critical scrutiny, they are really fun to listen to as a fan. And that’s the essence of this era: still great from a fan’s perspective but lackluster from a critical standpoint. I can highly recommend The Complete Recordings: The Columbia Years 1943-1952. It’s on iTunes for $100 and I see one on eBay for $130. It’s close to 300 tracks. For a sampler, there is The Best of the Columbia Years. 4 CDs. I see it, used, on Amazon for about $90. Here are your top ten Frank Sinatra recordings from the time between leaving Dorsey in 1943 and joining Capitol Records ten years later.

10. “Dream” (1945) — If you read part one, you know that a lot of Frank’s early material has tremendous nostalgic appeal. If you’re a fan of the ’40’s and ’50’s, this music takes you right there. “Dream” is the perfect example of this. It seems to shimmer as it descends from the heavens. Written by the great Johnny Mercer, it was a #5 song for Frank. He would revisit it – as he would many of this era’s songs – on 1960’s Nice ‘n’ Easy.

9. “April in Paris” (1950) — Everything I said for “Dream” I could say here. Another standard that young Frank sings wonderfully: “…no one could ever repriiiiise”. Absolutely gorgeous. Frank recorded it again seven years later for his Come Fly With Me album for Capitol. Also a signature song for the Count Basie Orchestra.

8. “Castle Rock” (1951 – with Harry James) — Here we have a real barn-burner. Columbia had the idea to re-team Sinatra with his old boss, Harry James, for three songs – two of which appear on this list. “Castle Rock” was an explosion of energy arranged by Ray Conniff. Sinatra and James both tear into this number, both sounding tremendous. Personal note: as I said, at this point in my life I owned very little of this music, Sinatra and Harry Connick among early purchases. Connick was known for singing standards in what could be called a ‘Sinatra vein’. Just before a James solo on “Castle Rock”, Frank exhorts the trumpeter to “go get ’em, Harry, for ol’ times sake!”. When I first heard this – not knowing Harry James was playing on it – I thought it was eerie that Sinatra seemed to be giving Harry Connick his blessing! Historical note: Harry James didn’t think much of this number. He called it “the worse thing that either one of us ever recorded”. I beg to differ, Harry.

7. “Sweet Lorraine” (1946) — You can’t really call Frank Sinatra a ‘jazz singer’. Except on numbers like this. Sinatra’s vocal ‘swings like a mother’ in this early example of his using his voice like an instrument; his phrasing and timing are perfect. Also perfect? The Metronome All-Stars jazz ensemble that backed him on this track. There are many great solos here and some great piano playing by a pre-superstar Nat ‘King’ Cole. “Sweet Lorraine” would also become a signature tune of his.

6. “Deep Night”  (1951 – with Harry James) — Another of the three numbers cut by the reunited Sinatra and James. This one – like the title suggests – is perfect late-night listening. Wonderful cadence and flow to Sinatra’s vocal and James summons up all the noir nuances possible in three minutes. Like he’s standing on the fire escape blowing over the alley. At one point, all the brass players join him in a few blasting notes before Frank comes sauntering back in: “Coooome to my arms, my darling…”.

5. “Saturday Night (is the Loneliest Night of the Week)”  (1944) — If you’re making a playlist of this era of Sinatra – and you’re not going chronologically – this is the song you start with. Not only for it’s blast-out-of-the-gates opening but for it’s lively horn arrangement and Frank’s swinging performance. This was one of his most notable uptempo numbers from this era. Great fun.

4. “Autumn in New York” (1949) — Much like “April in Paris”, here is a gorgeous song that Frank puts his quality stamp on. He would also revisit this on Come Fly With Me. Lovely string arrangement takes you right to a sidewalk in post-war Manhattan, golden leaves falling to the ground. Another standard, Frank’s is the only version to have charted in the States; number 27 in 1949.

3. “You Can Take My Word for It, Baby” (1946) — Sinatraphiles will look askance at this one ranking so high. On this little known track, Frank is backed by the Page Cavanaugh Trio, a group who borrowed heavily from the style of the Nat ‘King’ Cole Trio. Critics would lump this one among the lighter tripe that Sinatra recorded at this time in an effort to recapture the spark of his fading presence at the fore of pop music. I just think this tune drips with charm and is indicative of what is so good about this era of cozy, pleasant little ditties. It’s a wonderful light jazz performance.

2. “I’m a Fool to Want You” (1951) — Again, this tune not being #1 would cause me to suffer at the hands of music critics. Admittedly, if you had to pick 4 or 5 songs throughout Sinatra’s career that serve as signposts of where his craft was at a given time, this would be the brightest light of the pre-Capitol era. Some context is necessary to fully appreciate this recording. At this point in his life, Frank was smack in the middle of his tumultuous relationship with Ava Gardner. With similar personalities, the two stars would battle constantly. Frank felt everything in life deeply and when things were bad with Ava it greatly affected him. One of the few songs for which he has a songwriting credit, the Sinatra legend tells of him tweaking the lyrics to better reflect his situation with Ava. Another legend goes that, nearing desolation, Frank went into the studio late at night, laid down his gut-wrenching, emotional vocal in one take and walked out the same door, off into the dark night. Whether or not the one-take thing is true, what is true is that this is one of the most heartfelt performances of his illustrious career. He did revisit this for his “Where Are You?” album of 1957 but I don’t know why. His original ‘sounds’ like an open wound. Historical note: most Sinatra people will know of the absolute low point of Sinatra’s recording career, the novelty song “Mama Will Bark”. This abomination, recorded with non-singing actress Dagmar and actual dogs, was released as a single in 1951 – with “I’m a Fool to Want You” on the B side. Inexplicable.

1. “Poinciana” (1946) — Here, again, Sinatra people are going ‘what??!!‘. And here, again, I say it’s all about the charm. Frank’s only recording of this Cuban melody drifts into your consciousness subtly, seemingly from out of the ether. If you’re on a classic episode of The Twilight Zone and there’s an old radio in your grandmother’s attic that can transport you back in time, this recording is coming out of the speaker. There is a certain quality in this recording. Sometimes, yes, it’s a positive to say that a song is ‘timeless’ but, sometimes, what you really want is a song that is stuck in it’s time, is so very of it’s time. “Poinciana” is that song for me. It is just delightful. Frank’s plaintive “poiiiinciana…” is complimented by a lilting flute and sweeping strings. It’s dreamy.

Up Next: Frank Takes Over the World