I’ll always remember being asked by a friend who wanted to start a Frank Sinatra CD collection what he should buy first. As this was also early days for me collecting Frank I had to pause; what do you buy first? Also, around the same time, a family member bought the two volumes of Frank’s ‘greatest hits’ released in 1968 and 1972 and was sure to play them when I visited. Those two early compilations are anything but a collection of Frank’s best recordings but basically they compiled recent singles of his, not many of which are remembered by neophytes today. I remember thinking ‘poor guy. He bought these CDs and now he’s wondering why he’s never heard of these songs’. So, I’ve known from early on that Frank Sinatra is no regular artist, particularly where his catalog is concerned. Frank was a pioneer of the ‘concept album’, a term (like ‘supergroup’) that has been misused many times over the years. With the advent of the 33 1/3 RPM LP, Frank found he was able to tell a story over the course of 12-16 tracks that couldn’t be told on single 45s or any other format, really. He would plan his albums carefully, picking the songs, the arrangers/conductors/orchestrators and he would also choose the overall theme for the album: ballads and torch songs or swinging, uptempo numbers. One of the many things that sets him apart is the fact that he would go into the studio to make these albums and then, on separate dates, go in to record singles for the juke boxes. Therefore, Frank Sinatra became the first true ‘album artist’ and the public looked forward to each subsequent release. The singles kept the kids interested and kept him on the radio and in the diners. What does all this mean? It means that Frank became a pioneer in another way: the ‘compilation’ did not and does not function properly as a means by which you get the full impact of Sinatra’s artistry. To really understand Sinatra you almost have to buy ALL of his albums – the singles are good fun and some are outstanding but they do not represent his best work. The people early on who asked me what to buy? My answer really should’ve been “all of it”. This also illuminates a severe problem with my intention to highlight the best recordings of Frank’s career. I may give you three or four great lists but you will have to collect the albums that all these individual cuts are on to obtain all these songs – unless you have a subscription to a music service that would allow you to build a playlist. Along with his greatest recordings, we’ll also look at the albums that house these great tracks and present a case for buying each of them.

Frank Sinatra’s career is so unwieldy that I’ve broken it up into chronological sections. Sections broken up not only by years but by stages in Sinatra’s recording career. Again, the purpose of these posts is to inform you of what he was doing and when and what is the best of each era. We start, of course, at the beginning.

PART ONE: Boy Singer — Hard to believe, but the ‘singer’ wasn’t always the biggest attraction. That distinction went to the bandleader and the big band itself. A big band would have many parts or sections: brass, reeds, rhythm and singers. Quite often a band would have a boy singer, a girl singer and/or a group or chorus. The man widely considered to be the greatest interpreter of popular song in history, Frank Sinatra, got his start as a boy singer. Some of you will know that he was working as a singing waiter at the Rustic Cabin in New Jersey when trumpeter and bandleader Harry James came in, heard our boy and hired him. Frank’s first major professional work came with the James band and lasted little over a year but is a notable time, nevertheless. Firstly, while James’ outfit was not number one in the land they did enjoy success and put out some fine material. James himself has been called one of the greatest trumpeters of this era. In terms of recordings, Sinatra’s time with James is very notable thanks to a number they released in 1939: “All or Nothing At All”. This sublime record represents the first peak of Sinatra’s career but only gained traction on the charts three years later in 1943, by which time, FS had moved on.

Unlike the Harry James organization, Tommy Dorsey’s band was one of the biggest in the land, second only, perhaps, to the Glenn Miller Orchestra. When Dorsey had a boy singer vacancy, he approached James and Sinatra about hiring Frank. To his credit, James did not stand in Frank’s way and FS joined the big time. One thing certainly that would have been a challenge for the ultra-confident Sinatra was his middling status as simply the ‘boy singer’ in Dorsey’s group. Dorsey was a notoriously difficult taskmaster who didn’t brook any displays of ego. It was the BAND (and a little Dorsey himself) that came first. Sinatra had to keep himself in check but still applied himself to being a part of some of the finest recordings of the big band era. Years later, Frank had only good things to say about Dorsey. Frank would stand behind Tommy when Tommy would take a solo on his trombone. FS paid particular attention to Dorsey’s breath control; Frank would watch for the rise and fall of Tommy’s torso, indicating when the master was sneaking a breath to better play the long, languid passages he achieved on his instrument. Frank, though, was not content to stay in the background and would lobby for more prominent vocal work on the records and in live performances and also for having his and the other singers’ names listed on the 78s Dorsey was putting out.

Frank’s time with Dorsey was his first taste of stardom. His ‘bobby-soxer’ audience embraced him as a surrogate for the many men who were overseas fighting in World War 2. He was the most popular singer in the land and he enjoyed the type of worship seen only once before in the case of matinee idol, Rudolph Valentino. Frank’s recordings with Dorsey are definitive of the era. Do they match up with some of his spellbinding performances of the Fifties and Sixties? Well, no, but it’s different. ANY big band music has immense charm attached to it. ‘Nostalgia’ only begins to describe how wonderful this music is. It truly does transport you back to the ’30s and ’40s and along with that comes such cozy, wistful feelings. If you are a completist, like me, you need to own some Dorsey-era Frank. It’s part of what makes him unique. His 50+ year recording career checks off most of the boxes in music’s history, starting with the big band era.

As I’ve said, ALL Frank’s recordings with James and Dorsey are basically delightful. If you like big band music you will obviously love this era of Frank’s career. I’ve gone ahead and ranked these 10 tracks anyways but, really, it’s more like 5 or 6 are tied for 1st and the rest are tied for 2nd. I can highly recommend The Popular Frank Sinatra. It’s three discs that collects most of Dorsey’s recordings with Frank singing. There’s also an import I’ve seen on Amazon called The Complete Studio Recordings. It’s four discs for (currently) $14! I may get it myself. Here’s your Top 10 Frank Sinatra recordings, 1939-1942. All were recorded by Frank when he was with Dorsey unless otherwise noted.

10. “Whispering”  (June 30, 1940) — My comments on each of these tunes could all be the same: delightful, charming, make you feel like you’re sitting by the radio in a cozy, well-lit living room in the early ’40’s. “Whispering” is no exception. Wonderful, mid-tempo tune with great and fun vocals from all of TD’s vocalists.

9. “Without a Song” (January 20, 1941) — Recorded by Bing in 1929, Frank’s vocal here is an early example of him in strong voice. The lyric contains the unfortunate term ‘darkie’ which FS sings here but doesn’t in two subsequent versions in the 1960’s.

8. “The Sky Fell Down” (February 1, 1940) — Not much needs to be said about this track. Gorgeous muted brass, particularly Tommy’s smooth trombone playing. Frank drifts in on a cloud and it’s like Dreamland.

7. “I’ll Be Seeing You” (February 26, 1940) — A gentle, nostalgic song that has been a standard almost since the beginning. Bing had a hit with this one, as well. Dame Vera Lynn perhaps wrung the most emotion out of it but Frank’s wistful version with Dorsey is another perfect tune for rocking-chair listening. Lovely clarinet solo by Johnny Mince. Frank revisited it twice, once as a ballad and once with a bit more jump, both early ’60’s.

6. “East of the Sun (and West of the Moon)” (April 23, 1940) — This beauty is an early example of Dorsey going with a smaller group as opposed to a full orchestra. He achieved a jazzier sound with the Sentimentalists and this tune starts off with some wonderful muted trombone phrasing from the leader. Frank ambles in aided and abetted by the boys in the band singing hep lines behind him (“you can really lay it on me”). This tune is normally sung as a straight ballad but Frank really swings it.

5. “I’ll Never Smile Again” (May 23, 1940) — Little Canadian content here. Toronto songwriter Ruth Lowe wrote this sad lament after her husband of one year died during surgery. Fellow Torontonian Percy Faith debuted the song on the CBC. Lowe got the song to Tommy Dorsey who loved it and had it arranged for Frank. Another Sentimentalist setting featuring a celesta. This version was number one on Billboard’s first official national music chart. A gorgeous recording. Frank would revisit the song later in his career.

4. “The One I Love Belongs to Somebody Else” (June 27, 1940) — A lot of the best Dorsey/Sinatra sides are mid-tempo numbers that swing and have great interplay between FS and the other singers in the group. Here, the Pied Pipers echo Frank nicely with some more hep lines (“papa, you know”).

3. “Oh, Look at Me Now” (January 6, 1941) — Frank Sinatra continues to invent “swingin'”. In this finger-popper, FS shares the vocal duties with Connie Haines and the Pied Pipers. This is a good track for those who think this music is outdated. This is ‘cool’ before cool was a thing. Listen to FS in reply to the Pipers; “I’m a lover”. Swank!

2. “All or Nothing at All” (with the Harry James Orchestra, 1939) — One of Frank’s earliest recordings (he was 24 in 1939) became his earliest hit. But not right away. The song was released in 1939 and went nowhere. Then, in the midst of the musician’s strike in 1943 (look it up), this – and many other old recordings – was reissued and sped up the charts. It became the first of Sinatra’s 116 Top 40 recordings. The song itself, though? Fantastic. Frank is in strong, full voice and James has such a clear, ringing sound. This is another song Frank would record again throughout his career, most notably on the Strangers in the Night album in 1966.

1. “Let’s Get Away from it All” (February 17, 1941) — This extravaganza is ranked number 1 for many reasons. Dorsey shot the works here making this extra long (for it’s time) track two sides of a 78RPM and utilizing all seven of his singers; Frank and Connie Haines trading playful lyrics and Jo Stafford and the Pied Pipers providing breezy support taking verses themselves. Throw in some outstanding solos from TD and others and you’ve got a really fun travelogue. Listen close for some of the hippest vocalizing of the big band era (“off to Niagara – solid!”).

NEXT: Sinatra Goes Solo