Twelve Great Songs For The Frank Sinatra Centennial

This year marks the 100^th anniversary of the birth of the man that the veteran music critic Robert Christgau once called “the greatest singer of the 20^th century.” Frank Sinatra’s life and career are full of controversy, but Christgau’s assessment of him turns out to be a helluva lot less provocative than you might think.

It’s also hard to argue with the Academy Award-winning filmmaker Alex Gibney, who, in our Soundcheck interview about his new HBO documentary, Sinatra: All Or Nothing At All, said that Sinatra “dominated American culture.” 

Of course, it’s also possible for anyone born after, say, the mid-1950s to think of Sinatra as the guy who sang “New York New York” and “My Way,” and maybe “Strangers In The Night,” and wonder what all the fuss is about. I know that was my thinking as a kid who grew up on rock. Sinatra was my parents’ music. But then I got my first professional radio gig, at WFAS, a station in White Plains, New York. This station played a fair amount of Frank Sinatra and Tony Bennett – in fact, it was commonly thought that the call letters stood for Francis Albert Sinatra (they didn’t). Once there, I ended up getting a real education in why those two singers stood head and shoulders above all the other “easy listening” and “adult” records in the library.

So to celebrate the Sinatra centennial, I’ve put together a dozen of my favorite Sinatra songs. Most of his biggest hits are not on it. I’m not trying to be contrarian; but a lot of what I consider his finest moments came in ballads – the lovelorn, twilit songs that suited his slightly dusky voice so well, but maybe didn’t top the charts. Especially during the years in the '50s when his troubled marriage to actress Ava Gardner was falling apart, you can hear him living in those songs in a way that hurts so bad you can’t help feeling good. Also, you don’t need to listen to Sinatra sing “Someone To Watch Over Me” to know that it’s a classic song. On the other hand, some of my favorite Sinatra recordings are of songs that I’m not so sure would be classics in anyone else’s hands. 

So, here, in no particular order, is my "Sinatra Dozen." I hope you find one or two that knock your socks off. Because Sinatra can still do that.

“Only The Lonely” (1958)

From the album officially called Frank Sinatra Sings For Only The Lonely; you know, that famous Edward Hopper painting, Nighthawks, the one with a few scattered people in a late-night diner? This album could be the soundtrack to Hopper’s picture of loneliness, and if I didn’t rein myself in, at least half of this list would come from this record. The ache here in Sinatra’s voice is audible. The orchestrations were by the great Nelson Riddle, to my ears the best arranger Sinatra worked with by far; but since Riddle wasn’t available to conduct, that job fell to the renowned Felix Slatkin. 

“Witchcraft” (1957)

Released as a single, and sporting one of Nelson Riddle’s brassiest arrangements, Sinatra got to this Cy Coleman song first. Others have recorded it since, but this is one of those songs that Sinatra is most closely associated with. He recorded it at least two more times, but this 1957 original is notable for the apparent effortlessness of the singing. Make no mistake, the end of a line like “proceed with what you’re leading me to…” requires pinpoint control.

“Moonlight In Vermont” (1958)

Rock fans take note: The Beatles did not invent the “concept album.” In the mid-to-late-'50s, Sinatra did three brilliant ones: Only The Lonely (1959), its predecessor In The Wee Small Hours (1955), and Come Fly With Me (1958) -- which was essentially a musical tour of the world. Here you’ll find Sinatra doing “April In Paris” and “Autumn In New York,” both standards, as well as the somewhat less standard “Moonlight In Vermont.” This is where Sinatra’s breath control, learned from watching Tommy Dorsey play the trombone in the late 1930s, comes into play. Listen to a line like “Travel each bend in the road” and watch how his ability to shape a melody almost makes the strange leaps in the music (perhaps following the unusual, non-rhyming lyrics) seem natural.

“All I Need Is The Girl” (1968)

I can’t believe how many people don’t know that Frank Sinatra and Duke Ellington did a record together. A great record called Francis A. And Edward K., their respective given names. Yes, by 1968 both artists may have been past their primes, but there are no fewer than five absolute gems here, and my favorite is this uptempo number. Listen to that phrasing, the way he lags behind the beat when the line “If she’ll just appear we’ll take this great, big town for a whirl” comes back for the second time. Also, the Ellington orchestra takes an instrumental break, at the end of which Sinatra, whose idea of scatting seems to have been the “dooby dooby doo” in “Strangers In The Night” or an unfortunate “Jack!” inserted into random songs, makes the genuinely musical decision to come back in with a short wordless vocalise that fits the band perfectly.

“In The Wee Small Hours Of The Morning” (1955)

From what is often considered one of the first “concept albums” anywhere, In The Wee Small Hours, this is another Nelson Riddle collaboration. But frankly, it’s hard to get past Sinatra’s voice here: desolate, inconsolable, yet still tender and beautiful. Sinatra and Ava Gardner both had extramarital affairs, but he doesn’t seem to have been a big believer in what’s good for the goose also being good for the gander. Maybe that’s a good thing for us, since he was by all accounts devastated at losing her, and it shows in these songs.

“Old Devil Moon” (1956)

After the gloom and darkness of In The Wee Small Hours, Sinatra aimed for the pop charts again in his next album, Songs For Swingin’ Lovers. As I mentioned above, the jazzy "hepcat" side of Sinatra has, for me at least, not aged as well as the ballads and torch songs. But Riddle’s arrangements and Sinatra’s song choices on this record are first rate. And “Old Devil Moon” is the cream of the crop.  Well, maybe… but more on that later.

“It Was A Very Good Year” (1965)

The more I look at my list of Sinatra favorites, the more I realize I really am a Nelson Riddle fan. And when Sinatra is paired instead with Gordon Jenkins, who tended to slather on the strings, I begin to lose interest.  But here I have to say, Jenkins did a masterful job. You can have “My Way” (ruined for me by the R-rated version sung by my friends in school – “I did it sideways.”). If I’m going to listen to a bittersweet look back at a life well-lived, or at least claiming to be well-lived, then I’ll take this song. Each verse is another stage in the singer’s life, and while the music repeats, the orchestration changes each time – pizzicato here, a tremulous muted quality there.

“One For My Baby” (1958)

Another track from Only The Lonely, and possibly its signature tune. Written by Harold Arlen and Johnny Mercer, it is less a song than a four-and-a-half-minute film noir, as Sinatra’s character – really, Sinatra himself, you feel – tries to drink away his pain.

“Nice Work If You Can Get It” (1957)

If Sinatra and Riddle were going to tackle a song that had already become a standard, they were going to have to do it right. Sinatra swings, gently and without the exaggerated mannerisms of so much of his later “swingin’” music, and even sits out half a chorus so the orchestra can do some heavy lifting. I’m afraid I’m not as impressed with the 1962 version that Sinatra did with the Count Basie band, despite the big-name collaboration.

“What’s New” (1958)

This song is also from Only The Lonely, and a song that had already been sung by the jazz singer Helen Merrill a few years earlier -- although I didn’t discover her version until after this one. (It is wonderful.) Portraying a guy who's just barely keeping it together after running into his ex, this was never going to be a radio favorite, but man, is it worth spending five minutes with.

“I’ve Got You Under My Skin” (1956)

Another track from Songs For Swingin’ Lovers, and a total masterpiece arrangement by that Riddle guy again. I know, I’m contradicting what I wrote above about “Someone To Watch Over Me,” but in this case, Sinatra’s recording has become the definitive version of this Cole Porter classic.

“Willow Weep For Me” (1958)

Okay, a final track from Only The Lonely. (Sorry, “Angel Eyes” and “Ebb Tide.”) Not just another torch song, this one was written by Ann Ronell (“Who’s Afraid Of The Big Bad Wolf”), a notable figure in a songwriting world dominated by dudes.  And again, listen to that Nelson Riddle arrangement.

So you know how when you buy a dozen bagels, you get a 13th free? Well, here you go…

“Somethin’ Stupid” (1967)

A duet with Nancy Sinatra, this really is a wonderful little song of seduction. Nancy had already recorded her huge hit “These Boots Are Made For Walking” and was at the peak of her fame, and the merging of the two voices is as sly and seductive as the song itself. It just sounds great. Now if only I could stop thinking “Yeah, but this is a middle-aged guy and his daughter. Ewww.”