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Top 10 Sinatra Songs

sinatraI fell in love with jazz in high school and became something of an obnoxious purist, convinced that violins belonged only in classical music. At some point, though, I heard Frank Sinatra’s trailblazing concept album In the Wee Small Hours, arranged by Nelson Riddle, and realized I would need to modify my point of view. OK, I thought, I can handle strings in artfully arranged ballads, but that’s it. No up-tempo tune can possibly swing if there’s a violin on the premises. Then I heard Songs for Swingin’ Lovers and was forced to admit that Nelson and Frank had me again.

In James Kaplan’s Sinatra: The Chairman, Kaplan quotes Riddle talking about his work with Sinatra: “Most of our best numbers were in what I call the tempo of the heartbeat. . . . Music to me is sex—it’s all tied up somehow, and the rhythm of sex is the heartbeat.” That goes a long way toward explaining the enduring appeal of Sinatra and, especially, the Sinatra-Riddle collaboration. When the two met, it was clear to both that something unique was about to happen. Kaplan reports that as soon as Sinatra heard the playback of his first recording with Riddle, “Frank knew his life had been altered as irrevocably as it had been the first time he laid eyes of Ava Gardner. This was the thunderbolt, musically speaking.”

So it should come as no surprise that my list of favorite Sinatra songs, no doubt like those of every other fan, is dominated by Riddle-arranged tunes recorded from 1953 to 1961, when both were at Capitol Records. All of my top 10 come from those era-defining Capitol years, and all but two were arranged by Riddle. Want to listen while you read? Open my YouTube playlist in another tab and click play.

nice easy1. “Nice ‘n’ Easy” (from Nice ‘n’ Easy, 1960; arranged by Nelson Riddle)

Some Sinatra devotees might find this an odd choice for the top spot. The Nice ‘n’ Easy album was one of Sinatra’s last for Capitol, and in fact, it was recorded only to fulfill a contractual obligation before Frank left to launch his own Reprise label. And yet, to my ears, everything—from lyrics to arrangement to, yes, the “rhythm of sex”—that defines the Sinatra sense of cool is on display in this song.  At his best, except perhaps in the wee hours of morning, Frank always did it nice and easy.

wee small2. “In the Wee Small Hours of the Morning” (from In the Wee Small Hours, 1955; arranged by Nelson Riddle)

The first thing one needs to know about “In the Wee Small Hours,”—both song and album—is that Sinatra usually referred to it as “my Ava record.” It was recorded while the singer was still in the grip of the deep melancholy that engulfed him after his breakup with Ava Gardner, and he brings all of that to this first “concept album”—16 songs all capturing the mood of heartrending loss: “In the wee small hours of the morning, I miss her most of all.”

swingin lovers3. “I’ve Got You under My Skin” (from Songs for Swingin’ Lovers, 1956; Arranged by Nelson Riddle)

The jewel in the sparkling crown of this classic album, which captures Riddle’s heartbeat rhythm at its swinging, sensual best, was a late addition to the record. Sinatra was usually a one or two take singer (remember, the Capitol albums were recorded live with the band, without overdubbing), but this time he knew Riddle had delivered a very special arrangement and kept tinkering through 22 takes. Kaplan provides fascinating backstory on what went on in the studio, including the recording of trombonist Milt Bernhart’s stunning solo.

Frank Sinatra Sings for Only the Lonely4. “One for My Baby (And One More for the Road)” (from Frank Sinatra Sings for Only the Lonely, 1958; arranged by Nelson Riddle)

Three years after In the Wee Small Hours, Sinatra recorded another album of what he called “suicide songs,” and if anything, it’s even darker than its predecessor. For me, Only the Lonely isn’t quite as consistently excellent as Wee Small Hours (I’d argue Riddle actually overdid the strings in places), but when it’s good, it’s unbeatable. “One for My Baby” is, of course, Sinatra’s quintessential saloon song, and it finds him at his storytelling best, showing why singer after singer extolls his remarkable diction and careful reading of lyrics. Sinatra recorded this song many, many times, but this one is the gold standard, featuring his longtime accompanist and friend Bill Miller’s exquisite piano.

5. “I’ve Got a Crush on You” (from Nice ‘n’ Easy, 1960; arranged by Nelson Riddle)

Sinatra sang this song hundreds of times, too, and it’s on multiple albums, but, please, stay away from the live versions recorded late in his career. This is the one to play. Yes, “the many millions of Annabells and Lillians” would have been glad to capture Sinatra (and plenty of them did, albeit briefly), but it seems pretty clear when you listen to him sing the song that, even in 1960, he was still crooning about Ava.

Frank Sinatra Come Dance with Me6. “Just in Time” (from Come Dance with Me, 1959; arranged by Billy May)

If there are still jazz fans out there who haven’t made their peace with strings, even Riddle-arranged strings, then this swinger from arranger Billy May, who loved him some brass, is the song for them. Sinatra liked to think of himself as a jazz singer, and the hippest of jazzmen—Lester Young and Miles Davis, to name two—had nothing but admiration for Frank. You can see why here, in one his jazziest songs.

7. “Mood Indigo” (from In the Wee Small Hours, 1955; arranged by Nelson Riddle)

Later in his career, Sinatra recorded a fine album with the Duke Ellington orchestra, but his voice wasn’t quite as spot-on as it was during the Capitol years. This rendition of one of Ellington’s most haunting ballads obviously fits the Wee Small Hours concept perfectly, and Frank gives it a terrific reading, supported by Riddle’s luscious mix of reeds and strings.

8. “You Make Me Feel So Young” (from Songs for Swingin’ Lovers, 1956; arranged by Nelson Riddle)

This irresistibly jaunty arrangement opens the album, and, with Frank in great voice and Riddle teaching a postgrad seminar on how to use strings as accents, even on a swinger, it gets the record off on the perfect note (a full 180 degrees away from the suicide songs). The lyric promises to make you feel young even “when you’re old and gray,” and in the face of so much contrary evidence, I can testify that it still works for me, at least for a few minutes.

come fly9. “Come Fly with Me” (from Come Fly with Me, 1958; arranged by Billy May)

I pity anyone not old enough to remember when flying was an adventure—”Say the words and we’ll beat the birds to Acapulco Bay”—rather than a grueling and oddly pedestrian slog. At least the deprived young have this song to help them imagine what it was like. Of course, on another level, “Come Fly with Me” is an elaborate sexual metaphor—”We’ll just glide starry eyed . . .”—and listeners young and old will have no problem relating to that.

10. “Angel Eyes” (from Frank Sinatra Sings for Only the Lonely, 1958; arranged by Nelson Riddle)

Frankly, I have no idea why this song isn’t higher on my list. The minor key and the bent notes are transfixing, and the lyric could be the most pure noir statement in Sinatra’s repertoire. “My old heart ain’t gainin’ any ground cause my angel eyes ain’t here.” Obviously about Ava again, but this time he’s bidding farewell: “Scuse me while I disappear.” Sinatra ended his original retirement concert with that line; sadly, he didn’t disappear but unretired and went on for more than a decade, his voice failing along with his memory for lyrics. Still, in some ways, that’s an even more perfect noir finale. In the end, we all wind up being the doomed guy in a Jim Thompson novel, struggling to hang on.

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About the Author:

After more than 30 years at Booklist, editor and publisher Bill Ott continues to edit the crime fiction section of the magazine and still delights in discovering new hard-boiled writers. Follow him on Twitter at @Booklist_Bill.

1 Comment on "Top 10 Sinatra Songs"

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  1. I can’t believe you rated “Come Fly With Me” at #9.

    But, truth be told, they are all so great it is almost impossible to rank any of them.

    Thanks for the list. Love it.

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