Frank Sinatra and Nelson Riddle at Capitol Records studios

In 1953, Ava Gardner, the love of Frank Sinatra’s life, had left him. One of Frank’s best friends, the composer Jimmy Van Heusen, was planning to take him out and get him laid, get his mind off of Ava, as if it had ever worked before. But when Jimmy went to pick him up, he found Frank in a bathtub, wrists slit, bleeding out. Jimmy rushed him to the hospital. The incident was never reported. Everyone agreed it was best for Frank to go back to work.

Frank had just filmed a supporting role in From Here to Eternity, an Oscar-winning performance that would triumphantly return him to the public eye, after years of seeming like a has-been. But the movie hadn’t been released yet when he cut his first studio sessions for Capitol Records. Maybe because he was in a rut, or maybe because he was a genius, he chose old songs that had fallen out of favor with everyone except jazz musicians, many of which he had already recorded in his youth as a singer in big bands. Making the best of the new LP format, he grouped them into thematic units the length of a record.

What followed was a decade-long winning streak, lasting through most of the Fifties and the start of the Sixties. It’s one of the great bodies of work in popular music. It’s also the best way to acquaint yourself with a less clearly defined body of work, often called the Great American Songbook.

Sinatra is easily maligned as the classic Straight White Man, oppressively occupying the cultural center to the exclusion of others. This misses the point. The Sinatra canon should be credited to a multitude of authors.

His collaborators at Capitol were not just his brilliant arrangers, Nelson Riddle, Gordon Jenkins, Billy May, and Axel Stordahl, but the songwriters who, knowingly or not, contributed the material. Many of these great composers and lyricists were Jewish (Jerome Kern, Harold Arlen, Irving Berlin, George and Ira Gershwin), gay (Cole Porter, Lorenz Hart), African-American (Duke Ellington, Fats Waller, Andy Razaf, Eubie Blake), or female (Dorothy Fields, Carolyn Leigh, Kay Swift, Ann Ronnell). Add E.Y. “Yip” Harburg, which you should, and you can even include a card-carrying communist.

There are two reasons you want to hear Sinatra do these songs. One is because he assembled them into narrative arcs, inventing the concept album over a decade before it occurred to anyone in England. The other is because of how he sings them. Better singers have done these songs, and it’s unquestionably worth hearing Louis Armstrong, Billie Holiday, Sarah Vaughan, Anita O’Day, and a handful of others sing them. But while Sinatra’s versions are not necessarily the best, you might say they’re the most accurate.

Sinatra is the most authentic interpreter of these songs because his voice and personality, iconic as they are, exist only in service to them. He sounds so familiar now it’s hard to hear his innovation, but give some of of the less distinguished pop singers of the era a listen and his vision becomes immediately clear. Gene Lees has suggested that the uniqueness of his vocal approach has something to do with Italian-American vernacular English, given that Irish tenors were so prominent at the time. But there’s something even deeper to it: you might say that while lesser singers sang the melodies, Frank sang the words. Thanks in part to the technology of the microphone, which he was one of the first singers to incorporate into his technique, he rendered lyrics as speech. He borrowed improvisational ideas from jazz singers not to add ornamentation, but to make a highly structured piece of music seem as natural as a conversation.

Yip Harburg once said, “Music makes you feel feelings. Words make you think thoughts. But a song can make you feel a thought.” This was Frank Sinatra’s lifelong project. What follows is my entirely subjective guide to the sixteen LPs that form the core of his remarkable body of work.

Inessentials

16. A Jolly Christmas from Frank Sinatra (Gordon Jenkins, 1957)

This is fine, but with the exception of the transcendently, incongruously gloomy “Have Yourself A Merry Little Christmas,” these songs are just not up to the level of the rest of the canon.

15. This Is Sinatra! (Nelson Riddle, 1956)

Though Frank was spending the Fifties establishing the LP as an artistic medium, Capitol did release some singles that didn’t make it to albums, often written for this purpose by Jimmy Van Heusen and Sammy Cahn. Again, these mostly aren’t up to the level of the songs he selected elsewhere, but this singles compilation does have Harold Arlen and Ira Gershwin’s masterpiece “The Gal That Got Away,” introduced by Judy Garland in the second version of A Star is Born.

14. Come Swing with Me! (Billy May, 1961)

This album sounds a little weird, with the arrangements lacking strings or woodwinds, and the engineer going a little batshit on stereo panning. It’s good stuff, but lacks thematic focus; Frank had already started his own label, Reprise, and was clearly just riding out his Capitol contract.

13. Sinatra’s Swingin’ Session!!! (Nelson Riddle, 1961)

This is a warp-speed half hour. Nelson Riddle was Sinatra’s most sympathetic and distinctive arranger, with Gordon Jenkins representing a stately classicism on one side of him and Billy May a hard-swinging populism on the other. Here Riddle seems determined to out-swing May. It’s good, but the bar is too high in this catalogue for you to make this a priority.

12. Point of No Return (Axel Stordahl, 1962)

For his last Capitol album, Sinatra opted for a symmetrical endcap, hiring Axel Stordahl, who had scored much of his pre-Capitol work. It’s somber and perhaps slightly monotonous, but still lush and heartfelt. I’m a sucker for Mack Gordon and Harry Warren’s “There Will Never Be Another You,” which laments the loss of a primary love object even as it looks forward to its repetitions — this is also Freud’s definition of depression.

Successes

11. Close to You (Nelson Riddle, 1957)

Riddle’s arrangements are anchored to a limited territory here, given that the majority of the instrumental accompaniment comes from The Hollywood String Quartet. The chamber music atmosphere is a charming diversion in the catalogue, and there are some great songs: “Everything Happens to Me,” “It Could Happen to You,” “Blame it On My Youth.” But if you’re like me, you’ll miss the jazz rhythm section that makes Sinatra’s best music so unmistakably American.

10. Nice ‘n’ Easy (Nelson Riddle, 1960)

Generally, the Capitol LP’s are either sad or happy, one or the other, and immerse themselves fully in their emotional province. This breaks the formula — the only theme here is the relaxed feel of the arrangements, with the cover showing Frank lounging in an armchair wearing a cardigan, sans hat or tie. The songs are good, but if we posit that for Sinatra swing is about desire and the ballad about loss, these are forced to fall somewhere in the placid middle. If that makes this album less compelling than the others, it doesn’t make it useless; sometimes you just want to put on your cardigan and find sanctuary from both the pain of loss and the drive of desire.

9. Come Dance with Me! (Billy May, 1959)

This may be the most iconic album of the lot, a finger-snapping swinger that sounds like the soundtrack to a night out with the Rat Pack. But this is before that image began to calcify into self-parody — the songs are classics, and the buoyant feel of the arrangements is perfectly suited to the unifying theme of dancing.

8. Come Fly with Me (Billy May, 1958)

This has the most fun concept of any Sinatra album — world travel — and the multicultural implications make it the most sonically varied installment in the catalogue. It includes one of the more memorable iterations of a tradition: a title song tying together the theme of the album, written specially for the occasion by Van Heusen and Cahn. This also includes the intoxicating “Brazil,” one of many occasions in which a detail of a Sinatra arrangement insinuated itself into most subsequent performances of the song. A personal highlight: the stirring last chorus of “The Road to Mandalay,” a setting of a Rudyard Kipling poem. Belting the hell out of the last chorus is a signature Frank move.

Masterpieces

7. Songs for Young Lovers/Swing Easy! (Nelson Riddle, 1954)

These are actually two EP’s, which have been made into a pair since the CD era. They’re Sinatra’s first released recordings on Capitol, and introduce the format fully-formed: ballads on Songs for Young Lovers and swingers on Swing Easy, arranged to perfection by Nelson Riddle. These are full of iconic Sinatra numbers. “All of Me,” in which a lonely protagonist offers a succession of body parts to a lost lover. Cole Porter’s “I Get a Kick Out of You,” in which a jaded protagonist has built up too much of a tolerance to enjoy drugs. Rodgers and Hart’s “My Funny Valentine,” in which the protagonist might sound like a jerk if you aren’t listening closely, but is really closeted, self-loathing Lorenz Hart looking into a mirror.

6. Where Are You? (Gordon Jenkins, 1957)

I’m a partisan of the Gordon Jenkins records, in which the strings are so lush you sink into them like clouds. But these are storm clouds, dark and cold on the inside. This includes “I’m a Fool to Want You,” a rare Sinatra co-write that’s obviously about Ava Gardner, but my favorite is “Maybe You’ll Be There,” in which a hopeless romantic thinks he sees his ex everywhere he goes.

5. A Swingin’ Affair! (Nelson Riddle, 1957)

We’re at the point where the quality of this music is undeniable. Check out the blistering succession of imagery and internal rhymes in Rodgers and Hart’s “I Wish I Were in Love Again,” which express a masochistic urge for the pain of a bad relationship. Try Duke Ellington’s lilting melody for “I Got it Bad (And That Ain’t Good),” which practically conveys the lyric’s meaning by itself. This one also has that iconic Sinatra swagger, but don’t forget who else you’re listening to when you listen to him. Some of their best work is here.

4. No One Cares (Gordon Jenkins, 1959)

This is the most underrated Sinatra album. It’s also the most unremittingly bleak — apparently Frank joked that it should be packaged with a razor blade. Look at him on the cover, surrounded by people but totally isolated, sharing the company of only a drink and a smoke. This grouping of songs is exceptional even in its already exceptional company, set to some of Jenkins’s most astounding work: the first few bars of “Stormy Weather” rumble with Wagnerian thunder, the strings on “A Cottage for Sale” are like a gust of wind through an abandoned home, and “I Don’t Stand a Ghost of a Chance With You” sways with the dizziness of unrequited desire. It’s useful to have this record on hand at all times, in case of emotional crises.

3. Only the Lonely (Nelson Riddle, 1958)

Sinatra’s most famous ballad album, this ends with Harold Arlen and Johnny Mercer’s “One for My Baby (And One More for the Road),” his half of a dialogue with a bartender, full of frankness and Frankness. Along the way, “Blues in the Night,” by the same pair, is Riddle at his jazziest, and Rodgers and Hart’s “Spring is Here” is an aching depiction of depressive anhedonia with a knockout final couplet. The full title is Frank Sinatra Sings for Only the Lonely, and the cover shows his face painted like Pagliacci, the unhappy clown — it’s almost like he resents sharing his sadness with you. But he just can’t help himself.

2. Songs for Swingin’ Lovers! (Nelson Riddle, 1956)

If there are three and a half minutes in music more perfect than this version of Cole Porter’s “I’ve Got You Under My Skin,” contact me immediately because I need to hear them. It’s a good microcosm for the album as a whole: the hypnotic insouciance of its surface is threatened by an explosion of desire at its core, giving way to an outburst so pleasurable it’s impossible not to compare it to an orgasm. It’s not just that one — “Makin’ Whoopee” is so obviously about sex you may not want to think about your grandparents listening to it. Elsewhere, “Our Love is Here to Stay” was the last melody George Gershwin ever wrote, and Ira added words only after his brother’s untimely death. It’s a moving tribute to his brother, and it’s also a romantic love song if you want it to be.

1. In the Wee Small Hours (Nelson Riddle, 1955)

It’s no discredit to Sinatra and Riddle’s achievement that their first LP remained their best. The jazz band and the orchestra reach a world-historical dialectical synthesis, and the songs, dominated by Rodgers and Hart, are uniformly exquisite. Frank sings like he can’t get the taste of Ava’s lips out of his mouth — over fifty minutes, he makes your heart sink, flutter, and break a hundred times. The moment that hits me the hardest sounds something like Frank describing his job as a singer, on the nearly unaccompanied opening verse to “Glad to Be Unhappy”: “Look at yourself/If you had a sense of humor/You’d laugh to beat the band.”

Postscript

After Capitol, picking standouts becomes even more subjective. Francis Albert Sinatra and Antonio Carlos Jobim helped establish the Brazilian composer’s reputation, September of My Years was a return to form after rock concessions, Watertown was a surprisingly successful foray back into rock. Everyone who knows the material has other personal favorites.

Mine is his penultimate LP, 1981’s She Shot Me Down, which makes an art form out of being past your prime. It’s full of allusions to the Capitol era, bringing back Gordon Jenkins, and with an appearance by Nelson Riddle on a medley of familiar tunes. The program includes a brilliant but rarely done Stephen Sondheim song, “Good Thing Going,” and the high kitsch of Sonny Bono’s “Bang Bang (She Shot Me Down).”

Sinatra is pictured on the cover in a mise-en-scène reminiscent of No One Cares, shrouded in a cloud of smoke, glass of whiskey neat before him. Once the best-dressed man in America, here he no longer bothers, his paunch and his wrinkles betraying his old age. The theme of aging without grace is reinforced by the thoughts of regret expressed in each and every song. In spite of his diminished voice, worn down by years of booze and cigarettes, and by the years themselves, he still makes you feel those thoughts like no one else can.