Teach Me Tonight

Elena Passarello

00:00 / 00:00

Whether it is a ballad, a hill-billy, a swing number, a novelty song, a marching song or a comedy number, the popular song has that special something which makes people forget their troubles and cares. —“Tips on Popular Singing,” p.4

PREFACE (and a Word of Commendation
by Tommy Dorsey): p.3

In 1941, the Embassy Music Corporation printed “Tips on Popular Singing by Frank Sinatra,”1 a short text—little more than a pamphlet, really—by the singer and his coach, John Quinlan. “Everyone can sing a little,” the manual insists, assuring its reader that “the popular vocalist who has had voice training, beyond a few simple exercises, is the exception rather than the rule.”

Sinatra had just broken Bing Crosby’s six-time streak as the Downbeat vocalist of the year, and Billboard had also bestowed him with a similar title. He was the solo vocalist of Tommy Dorsey’s orchestra, the top band in the nation, and his “I’ll Never Smile Again”2 had held at number one through the previous summer and fall. He was twenty-six and did not read a note of music.

Even though, decades into his solo career, Sinatra would sometimes declare that he never took one voice lesson, most confirm that he spent his early twenties working on and off with Quinlan, an Aussie Bel Canto tenor fired from the Met for drinking on the job. The Sinatra that arrived at Quinlan’s apartment for his first one-dollar lesson was shifty and marble-mouthed, but his voice had spirit. It carried the post-teen passion of a spoiled but driven music nut who had already decided a) that something inside him deserved to be heard and b) that popular songs were the only way he could make a big enough noise to satisfy himself.

Even as a Hoboken nobody, Sinatra had ideas about singing, gleaned from a lonely childhood spent worshipping both radio and the musicians that passed through town on the way to New York gigs. Though his young voice was tight and much less expressive than the voice we now know as his, Sinatra had already begun straining toward a sound that was cufflinked, pedigreed, and better-than. You can hear this in the apprentice-level sounds of his first recordings, pre-Quinlan. You hear the American songbook squirming inside his neck, excited to get unstuck.

Quinlan began by training Sinatra’s body from feet to pelvis to neck to temples, remolding it as a reservoir for polished tone. His breath was inflated to accommodate long, smooth notes with constancy. The mouth that, in speech, wrenched itself into Joisey knots was reprogrammed into masks of widened, relaxed singing positions. These masks—a face for every phoneme—were cross-referenced with different modes and shifts in melody, which made all Sinatra’s sounds blend into one another.

By 1941, five years after his first Quinlan lesson, the Sinatra sound figure-skated out of the nation’s radios, a presence you knew to be his at first note, a flood of lacquered sound. The thirty-two-page “Tips” claimed it could work similar magic on any interested body and face, for just seventy-five cents.


The first lesson of “Tips” is an embarrassingly easy one. “It is suggested that the student listen to the records of as many different vocalists as possible, take, for instance the Vallées, the Columbos” and—though it could’ve gone without saying—“the Crosbys.” Sinatra met Quinlan already having completed that first day’s homework; he was the rare child of the 1920s who had not only his own bedroom, but his very own Atwater Kent, at which he knelt every day after school. A Bing Crosby poster hung over his bed. By the time he was sixteen, singing local weddings and rallies for sandwiches, the neighborhood knew him as the skinny doofus who swanned about in Bing chic: yachting caps, ascots, pipes.

Crosby was a sensible choice of idol, as he, more than any other crooner that “Tips” cites, made Depression-era radio more exciting. The first crooners embraced that miracle of twentieth-century sound, the studio mic, by singing in low and heartfelt styles that countered the blare of the bandleaders and the busy vaudevillians. While Jolson,3 Durante,4 Prima,5 and Calloway6 shouted to fill noisy halls, early radio sheiks Vallée, Columbo, and especially Crosby sang close and ornate, as if the screen of the radio speaker were the lattice of a confessional window.

As Bing and company popularized singing in close-up, Tin Pan Alley heated up crooner lyrics, to the point where they bordered on purple. By the time Sinatra met Quinlan, many writers were composing lines too schmaltzy to sell with a straight face. “Tips” also mentions singer Bob Eberly, who used a mayonnaise tenor to gloss over lines like “To me your voice is like the echo of a sigh / and when you’re near my heart can’t speak above a whisper”7 and handsome Jack Leonard, Tommy Dorsey’s top voice until Sinatra took over, whose forthright, almost hunky baritone takes the sting out of turgid lines like “you are the breathless hush of evening / that trembles on the breath of a lovely song.”8 The lesson here, in both Eberly and Leonard, is that to stay afloat on these new crooner lyrics, you needed to get a strategy.


“Tips” devotes most of its pages to sixteen chromatic passages, sung in fragments of near-gibberish, which the pupil is to repeat again and again, building the muscle memory of his breath, face, and chords. Many witnessed Sinatra singing a few of these exercises, like “let-us-wander-by-the-bay,” (number three) and “that-is-all-for-to-day,” (number sixteen) into his seventh decade. Some passages are weirdly food-obsessed, like exercises seven (“eat-your-beans-and-bar-ley-too”) and ten (“give-that-boy-some-bread!”).

Other lines smack of the same heat that wafted from Sinatra’s boyhood radio. Exercise fourteen, for example, could be from a prewar ballad: “the-night-is-long / and-you’re-so-far-a-way,” sung in scales to the tune of a chiming clock. In order to sing exercise fourteen properly, “Tips” coaches the singer down to each twitch. In order to both make a beautiful noise and sell the sentiment of the line, he must use vowels as his ballast:

Begin with just a little mouth opening on the word THE, and open wider on NIGHT. The word IS calls for a small opening, with the upper and lower teeth barely touching each other…. Open again on LONG…. Then, after taking a breath, sing the word AND with only a slight mouth opening, and hold this position until the end of the phrase.

It is easy to picture Sinatra absorbing this particular rudiment because following its instructions proves how minute mouth changes can yield a lyric’s intent. As the lips expand and contract, they create an audible passion. Try speaking “the night is long and you’re so far away” the “Tips” way yourself, making sure to change your mouth shape as per the above instructions. See how the long-sung vowels of NIGHT and LONG showcase the evening and its endlessness? Feel how the tighter mouth gives the last six words a receding clench, as if the distance between the singer and the “far away” sung-to are too painful to articulate with a full throat?

Such phrasing is the first major pillar of Sinatra’s Greatness-with-a-capital-G, because nearly every damn line of his discography, even turkeys like “Mama Will Bark,”9 is this full of color and nuance. His take on a song is always a joyride of shape and dynamics, caressing the sound at every turn, while cranking out perfect wavelengths of covered tone. Half the thrill of listening to him is in the surprise of the next wide or narrow or throaty or puckered syllable, and how it mirrors the flow of a song’s special story.

Sinatra sang these action-packed syllables with the attention of a good pupil for fifty years. He used the ballast “Tips” gave him to outlive nearly all his producers and collaborators, making “Tips” sounds past the birth of Rock and Roll and the death of Disco and the discovery of Grunge. He sang them alongside Fitzgeralds and Armstrongs and Clooneys and Davises, Jr. Alongside the Diamonds and Jobims and “King” Coles and Pavarottis. The Streisands. The Bonos. This “Tips” coaching aims for the exact delivery that shaped what is arguably America’s longest singing career. It was a sound that was popular both for its refinement and for its ease: a girded, articulate, and balletic voice. And also, if we are to believe “Tips,” a teachable one.


At the end of the sixteen lyrical exercises is a page without any words, just five hand-drawn mouths making the shapes of the five vowel sounds: AYE, EE, UH, OH, and OO. A “Tips” singer is advised to treat each vowel as a fixed gesture, like the hand choreography in “YMCA.” While Sinatra did allow himself to play with consonants—dropping g’s, fusing “th” into a street tough “t”—these five fixed mouths herded his vowels, keeping them ahead of the teeth to ensure crispness. It’s an edict Sinatra heeded so well that his sounds are often mimicked as chewed. Find any tribute artist from Atlantic City to Branson, and the fake Frank’s mouth will vogue through every vowel face on page 31 to first sing “Fly. Me. To. Tha.” and then end in the extended flex of the twin OO in “Moon.” Because the vowels, all Sinatras know, are where the action is.


Mouth Position #1: UHThe UH vowel in “Tips” is a fine place to hear Sinatra separate himself from the crooner pack, as it was cellular-level choices like the ones in his UH that readied him, out of all the boy crooners, to best Bing. While Bing and his wannabes would open up for a tall and bright AH sound, Sinatra sang it UH, adding a pinch of guttural thrust. Where Bing Crosby would sing a plucky AH in “Too-ra-loo-ra,”10 bumping the vowel ever-so-sweetly like an avuncular bassoon, Sinatra sang the “all” in “All the Way”11 with a kind of unh-unh bump that no one should ever associate with her uncle.

This is part of the joke of “Swooner Crooner,”12 a 1944 Porky Pig short which portrays Bing and “Frankie” as roosters singing to the hens of Porky’s Flockheed egg factory. At the end of the day, when the two have crooned acres of eggs from the Rosie-the-Riveter hens, the pig asks them, “Gee Whiz, that was swell, fellas. Howdya eh-may-eh-may-eh-make ’em lay all those eggs?” The roosters answer in unison, “It’s very simple, Porky. Like this....” And then the Bing rooster—in a Hawaiian shirt, tapping a pipe—huffs a perfect “ah-boop-ahboop-ahboop-ahboop-ah-boop,” while the Frankie rooster—bow-tied and skinny as his mic—lets out a baritone bell tone “Uhhhhhhhhhhhhhh!”

This is the UH of “Tips,” nervy and romantic, almost pelvic. A fresh way to get a chick to lay an egg. You can hear the voice actor who plays the Frankie rooster follow the “Tips” advice to “not spread from ear” and to “pay strict attention to the jaw,” which helps drop the AH tone to both the basement of the mouth and the sweet spot of the chest. Puffed up, stomach in, he might have even leaned away from the mic to douse the UH in thick Sinatra power.

Just as Bing’s intimate croon awakened something in young Sinatra, that tiny change from AH to UH was punk enough to make young postwar listeners, flush with cash and hormones, take notice. So when Sinatra made the final word of “All or Nothing at All” a lofted F-note sung as UH, female listeners too young for nylons heard its new power, glossy as the curl Sinatra Brylcreemed to his forehead, and they heeded it.

They ran to Dorsey Orchestra gigs, shouting through the instrumental numbers for more songs with that revolutionary Frankieee feel. And after absorbing that UH, his audience released a sigh so big that the Draft Board briefly classified Sinatra’s body 2-A, as his singing was “Necessary to the national health, safety, and self-interest.” That long, deep, sigh was not an “ah” of relief, but something else entirely.


A “Tips”-taught breather inhales as he normally would, but on his exhales, he yields his natural breath to the melody, holding out to please the phrasing of the song. This requires major inhale power, which Sinatra earned after dozens of hours of eat-your-beans-and-bar-ley-too. “Tips” coaches its pupils further, stressing that exhales can be jarring, and when they must happen, they should never produce audible air. In short, nowhere in a popular performance should there be breath that is not pulling melody with it.

This is probably why it is so rare to hear Sinatra breathe on tape. Breath, he once said, could murder a record. A microphone coquette, he’d swing the hinges of his elbow and neck in opposite directions, pushing the handheld mic close for “and did it…” but shunning it for the inhale, and then reeling it back only just in time for “…my way!”13 When he stood behind a mic, he asked that its stand be black, to fade into his suit. To further guarantee he could outlast the long phrases, he swam (some say he even sang underwater), took long walks, played vigorous golf, and borrowed Tommy Dorsey’s trombone trick of taking cheat swigs of air from the corners of his mouth when nobody was looking.

This absent breath was one of Sinatra’s careful gifts—a rule he lived by, like wearing jackets and ties in Jilly’s pool room. Erasing the breath united the song, the mic, the lungs into a unit, dissociating singing from everyday vocal work, like speech. On 1955’s Songs for Young Lovers, the engineer only trapped a handful of air across all eight buoyant tracks. In “A Foggy Day” or “I Get a Kick out of You,” he just leaves where there should be breathing—a disappearing act. Then, after the inhale, he returns to the song, grabs the listener by the wrist and tightens his grip—a trapeze man fresh from the bar.

So how might such a principled breather take Jennifer Holliday’s center-stage lungs in “And I Am Telling You I’m Not Going,” a song whose emotional stakes are miles higher than any in Young Lovers, and one whose title takes an entire breath just to say? At the 1982 Tonys,14 Holliday’s breath is more a part of the show than anything. Miked in the wings, in the floor, in her hair, she can’t escape it as her character, Effie White, tries to sing her way back into her career and into the arms of the man who has left her. Between each note of the song, she corrals air and presses it from her body in squalling buckets-full.

Her pantsuit bunches as she braces the stage floor; her makeup beads and her jaw hinges like a cash register all from the work of this breathing. The audience watches it wring her into knots. And as her fists punch more air into her mouth, she releases breath in sputters, chirps, and some of the most forceful notes ever associated with Broadway. They are dirty notes—sometimes flat or adenoidal—but, when phrased with these desperate, hulking breaths, they are strangely musical.

The house first goes apeshit for a ten-second belt with no break for breath, and then they lose their minds because she breathes: 266 seconds in, between the lyric “you’re gonna love” and the last word “me,” she devotes a suspended half-second not just to inhaling, but to stuffing six thousand cc’s of air down into herself in an uncorked suck. It is the sound of a hero resurfacing after three minutes under treacherous water, or of a dagger entering the heart of a Jacobean avenger.

The note she voices with that sucker-punch breath, a cheerleader-loud “ME!” that wavers in and out of tune, is meaningless. Because the breath is what resonates in the theater; it is the real music of the song’s trite rallentando. It is the sound of a trained singer who knows that the only way to sing like a woman desperate enough to break any rule in the book is to break the major rules of singing. “Tips” be damned.

Thirty years later, singers who cover “And I Am Telling You”15 still gulp that last breath, as if it were scored on the staff alongside the fermata.


Mouth Position #2: AYENineteen fifty-seven was a banner year for the vowel that “Tips” spells AYE and rhymes with WAY, and not just because Sinatra recorded “A(ye)pril in Paris,” “Ba(ye)be Won’t You Please,” “The Night We Called It a Day(e),” The Road to Mandalay(e),” and “Put Your Dreams Away(e) For Another Day(e).” That year also brought eight charted singles for Little Richard, who puts his AYE up just behind his front teeth—more like AIE—so he can sing the vowel bright and dandy in songs like “Rip It Up”: “got me a daite and I won’t be laite! Pick her up in my aitey-aite.”16 It was also the year of “Whole Lotta Shakin’,”17 in which Jerry Lee Lewis twangs a preacher’s AYE for “shakin’,” “shake,” and “baby.” And finally, for all twenty-eight minutes of 1957’s The “Chirping” Crickets, Buddy Holly rolls both corners of his upper lip toward his nostrils, then bounces the AYE to either his sinuses or his gullet for “that’ll be the day-AY-AY”18 and “MAY-be BAY-by”19 and “uh-HAY-HAY.”20

Lewis was seven when “Tips” was published, Holly was six, and Richard was nine, but it’s worth wondering if they ever got their hands on an old copy as kids, because their 1957 TV appearances show Sinatra’s “Mouth Positions” taken to absurd places. On the Steve Allen Show,21 Lewis mugs through two entire songs, maintaining the fixed faces of “Tips” even when he isn’t singing. As he vamps on the keys, Lewis stares into the camera like a blow-up doll in a curly wig, his teeth bared into the AYE-mouth and his eyes wide. Of course, a mouth this locked can’t enunciate, so the lyrics barely make it out of his frozen jaw, and the line “well, we’ve got the bull by the horns” comes out weehweegottaboooobahdahooorn. Buddy Holly’s mouth is smaller, a rectangle with rounded corners like a 17-inch Westinghouse set. In a December 1957 episode of Arthur Murray Party,22 he takes exaggerated pains to sing “pre-tty-pre-tty-pre-tty-pre-tty-Peg-gy-Soo-uh-oh-PAYE-ggy” as an animatronic run of all five “Tips” shapes.

Though their eccentric AYEs seem to mock vocal propriety, each singer follows a pop tradition forged by Sinatra and “Tips.” In The “Chirping” Crickets, High School Confidential, and Here’s Little Richard, each vocalist recorded and promoted his own “showcase vowels” to the populous. The voices of early rock, Elvis included, all gave the vowels of their lyrics an immutable stamp, and this is what Sinatra did in the 40s and 50s, with vowels that turned the crooners into balladeers. For a decade and a half, the UH of pop music was Sinatra’s UH, and the AYE was his, too. Billboard and Downbeat sanctified the velvety top roundness of his AYE and the very slight “ee” he pins to any AYE on a line-break (“I did it my wAYEeeee”).23 These were vowels, Embassy Music Corporation said, righteous enough to be publishable.

So perhaps, when we hear Lewis, Holly, or Richard sing the motley AYEs of 1957, we hear the young singers’ bids to own a vowel like real estate, to have a cartoon mouth drawn in their honor. To control the AYE, but probably for just a few years, as there are few mouths which popular music does not outgrow.


“Tips” insists that a popular singer’s throat be swaddled and monitored like a NICU baby. Quit practicing whenever the throat feels stretched, it says, and treat even the slightest tickle with hot water, lemon, and doctors. It warns all singing bodies to “keep the feet dry and avoid sitting in a draft,” though it is surprisingly tight-lipped regarding cigarettes or booze. Sinatra heeded these directives as faithfully as he did the vowel lessons in “Tips.” Many of his entourage noted that he washed his hands two dozen times a day and changed his boxers at least twice on show nights. When he had his druthers (which was often), he recorded in the evening, after his throat had been given hours to loosen. And he rarely used his voice off the clock. Ava Gardner only remembers one private concert in all of their six fiery years together, when he sang her to sleep24 during a bumpy jeep ride across East Africa.

The prime motivator for all this throat care was fear. Sinatra’s voice was legendarily fragile, as toxins, overuse, and even emotional turmoil bled all over his session tapes. Worse, sickness or stress had been known to silence him. After one strep diagnosis, he spent a week of vocal rest in an oxygen chamber, miming hand signals to his valet. And his career almost ended in 1951, when, crippled by a doomed love affair and a dirty fight over his Columbia contract, he suffered a “submucosal hemorrhage” onstage at the Copa, during the most inopportune phrase of “Bali H’ai.” His throat just gave: not a crack, but a mutiny that was, of course, written up in all the trades. He allegedly tried suicide that same year.

At thirty-five, smack dab in what experts call the peak of a trained baritone’s years, Sinatra was slapped with a reminder: that singing is a gerrymandered bodily function, even more so than speech. For all the research and methodology humans have applied to it, enough of singing’s processes are still equal parts magic, blind faith, and—worst of all—confidence. Sinatra’s voice, which Gay Talese called an “uninsurable jewel,” was also an unlocatable entity that could be trained, but not trapped. Though the regions of the body most responsible for singing are easily monitored, singing itself does not calcify or clot. It cannot not be X-rayed or splinted, like our other breakable body parts. For the voice is not a body part at all.

Maybe this is what those early rockers were fighting: Sinatra’s devotion to a ritual that could not be guaranteed. They pushed back at the fact that, even if a traditional pop singer followed all the edicts of vocal health and exercise, he still had to worry and pray just to keep his phantom instrument in a bankable order. To the oncoming waves of rockabillies, folkies, invading Brits, girl groups, glams, goths, new wavers, jam bands, metal heads, screamo kids, and arena rockers that followed Sinatra, this might have been a fate even more claustrophobic than the “Tips” straitjacket: that old-school squares who played by all the sonic rules could still fall prey to throat revolt.


Mouth Position #3: EEThe opening lyric of the absolutely perfect album Frank Sinatra Sings for Only the Lonely is “each,”25 which he sings not with a say-cheese grin, but with lips puckered and a yawning soft palate. This makes an unusual resonant bowl under the roof of his mouth, and it gives each “each,” “lonely,” and “weep” on the album a jazzy bell-tone sound with a dark, blue center.

There is a fitting solitude in singing the smile out of an EE for songs like “It’s a Lonesome Old Town” and “One for My Baby (and One More for the Road).” Writer Murray Kempton said Sinatra’s voice “breathe[s] the loneliness of the heart,” and this is what we hear in the EEs of Only the Lonely. They echo in his mouth as if they sit in cavernous rooms, alone with their blue thoughts. Paired with Nelson Riddle’s lush arrangements, the album is by far Sinatra’s most intense and artful moment: a wizened treatise on adult longing without a vocal seam in sight. As listeners, we revel in how a dead-sad sound can offer songs that jazz us. Or in how, as Kempton puts it, Sinatra’s singing “made us glad to be unhappy.”

The only lonelier EE than Only the Lonely’s EE belongs to Jimmie Rodgers, “the Singing Brakeman,” who often said his tips on popular singing came from boxcar tramps and fellow railroad workers. From 1927 to his death in 1933, Rodgers recorded not one, but thirteen songs called “Blue Yodel,” all of them covering low-down moments from a solitary life: hard work in mean-ass towns, his decade-long struggle with tuberculosis, a lover named Thelma that deserves to be shot. He charts the pain of each “Blue Yodel” with a notched trip up the throat, from his wry tenor to the sweetest head voice this side of Vienna: ...ah-dee-oh-lay-EE-oh-lay-EE-oh-lay-HEEE.26

The sonic thrill of any yodel is a vocal byproduct, something Sinatra learned to mask early on: the rough “break” in the voice as it pops from chest to head. And the vowel that best showcases a break is an EE, sung with a smiling mouth, the sound placed so far back in the throat that the note clacks: “yodel-aye-EE-hoo!” So Rodgers’ “Blue Yodel” refrains are Only the Lonely turned inside out: nasal tattles of the throat-at-work, ending in a busy, almost baroque, finish.

And just as the sounds are divergent, so are the colors of their loneliness. Sure, both riff on the bummer of twentieth-century solitude, but the details of each are distant as a Hopper painting is from a Grant Wood. And their vowels are the medium for this. Up in his yodel, Rodgers amplifies the pain of failing health and life on the dole by jumping from the collective human speaking range to the EE-hurt in his solitary, worried mind. Thus, the yodel break is the hurdle a man must audibly jump in order to tell us a personal truth. A Rodgers blue yodel yields a skint and walloped EE, the EE of a poor man who will be dead before his thirty-sixth birthday.

Sinatra’s weary pain, on the other hand, is a Beau Brummel pain. It has health insurance. Through learned technique, he has squeezed the emotion of the vowel into a sparkling solitaire. This, then, is the loneliness of a mid-century man in his prime: forty-something, holding the world by the shorthairs, but somehow still empty in his Jack Taylor suit. Those jazzy EEs tell us that, no matter how low he gets, he’ll still sleep in his warm bed tonight, then wake up and just get on with living, for as long as living may take. It’s a more complicated kind of lonely, and with each EE, it brings a darker and more luxurious hurt.

“Be careful what you wish for, Joe,” Sinatra’s EEs warn, and then he tips us a fifty and walks out into the street.


Mouth Position #5: OOBecause here’s the thing about EEs and AYEs and OOs: they are the atoms of song, the closest the human voice gets to the bell of a trumpet or the hole in a guitar. And if the voice that shapes them is striking enough, naked vowel lines can outrun any articulate pop lyric. Deep vowels work harder than punnery or allusion or throbbing adjectives; they don’t require the brainpower of Gershwins or Leibers, or even Smokeys. Smokey Robinson, titan of “The Way You Do the Things You Do” and “Tears of a Clown,” learned this firsthand in 1964, when an OO fell out of his mouth, and he knew to get the hell out its way.

He says he was onstage with the Miracles, vamping mid- medley, when a particular OO melody line popped into his head “quite by accident.” Sung sky-high and feathery in a sol-fa-mi interval, the OO was more than a hook, it was an anchor. It chained Smokey to a persona he hadn’t even written yet—a lover begging OO for forgiveness and getting turned on as he grovels. Later, he scripted that OO into the chorus of a Billboard Top 20 hit whose verses, though still in national airplay today, most listeners could not parrot back to you. The OO(o) line of “Ooo Baby Baby”27 is all they need to remember.

A year after “Ooo Baby Baby,” Sinatra recorded his most famous OO, which, like Smokey’s, was never part of any legit lyric. He is said to have hated the song in question, a limpid ballad with trite end-rhymes about a one-night stand made good. When he blew through the recording of the song in just two studio takes, he added a somewhat snide “dooby-dooby-doo”28 to the fade-out. This famous adlib carries a surprisingly butch OO, with none of the smitten bubbles of Smokey’s. It also lacks the demureness of “Tips,” which teaches that OOs need only be gentle OH-sounds with the lips “protruding slightly.”

What we hear in Sinatra’s “dooby” OOs is schmaltz tinged with rage; it’s got to be the angriest OO in the Easy Listening catalogue. And, perhaps for that reason, it became his first number one in a decade. He performed the song for over thirty years, sometimes stopping the band to ask the crowd why they wanted to hear such a lemon for the umpteenth time. And, for a couple of those decades, his reluctant reprisal would include that scat outro, once a felt improvisation, now a stone tablet he was sick of carrying.

“Strangers in the Night” was part of his last full set,29 in Japan in 1994, and it fared better than other tunes on the fourteen-song bill. He still found his core pitches and clung to them, his mouth working from AYE to EE to UH like it always did. But his range was half-gone, his breath pedestrian, and all the tones of “Tips” had suffered from cell death. By his final verse, Sinatra’s UH had collapsed, the AYE in “strangers” pinched, and the EEs of the song fizzled into the orchestration like an afterthought. He did not even bother to “dooby-dooby-doo.”

Still, these final tours were not as deflated as many singers’ last acts. The New York Times marveled at his “spontaneity of phrasing and intonation,” and how he “still seemed compelled to experiment, trying out little tricks of phrasing, indulging in impromptu scoops and dives and interpolations that worked.” He was pushing eighty and moored to a stool, but still visibly fighting, even for this song that he hated. Yes, his gaze sharpened and faded over the course of the swan song in Japan, but when his eyes were clear, Sinatra glowered into the house, alive with the task of storytelling, straining to tell all the strangers in the Fukuoka Dome this loathsome tale of an anonymous fuck with a happy ending.

It is in this straining that we hear the rule of “Tips” that Sinatra broke from the get-go, a rule he continued to ignore straight through to his final vowel.


After haughtily declaring at the end of the manual that the reader “will, undoubtedly, notice the marked improvement in [his] voice,” “Tips” ends its lessons by daring the reader to pick any song “of medium range” and to sing it. If the student has followed the instructions, it says, the voice now knows what to do, just open wide and sing “in a natural way, without straining.” And this is the last tip it offers.

But straining is the one thing Sinatra did, without fail, from Quinlan on. Along with those iconic vowels and disappearing breaths, we always hear Sinatra straining to prove himself worthy of popular song.

We heard him, in his twenties, newly-wed and dewy, straining to summon the burdensome sorrow in “After the years / I can’t bear the tears to fall / so, softly as I leave you there.” And we heard him again,30 past forty, having sung “Softly as I Leave You” so many times that he strained to remember soft exits and what they were like, three wives ago. And we heard him in between youth and middle age, singing his rudiments, drinking hot tea and checking windows for drafts, straining to prove that, no matter the song Columbia threw at him, he would dig right into its organs.

Astoundingly, nowhere in “Tips” is there a mention of understanding the songs that you sing. This is shocking because, for one, it is the Quinlan lesson Sinatra remembered into his senior years. In the liner notes of his last compilation CD, Sinatra cites Quinlan not on tones or air or beans or barley, but as the man who told him “you can’t sing what you don’t understand.” Learning this “understanding,” both authors must have known, cost a hell of a lot more than seventy-five cents. So they didn’t even bother mentioning it.

Only occasionally does a singer’s life run dead parallel to his understanding of a song, and even then, there is a strain that shakes the music around it. With Sinatra, we hear the direct understanding in “That’s Life,” in “My Way,” in “Nancy with the Laughing Face,” and in 1957 when, in the midst of his bust-up with Ava Gardner, he burst into the studio, took a flying leap at “I’m a Fool to Want You,”31 and then stormed out after one five-minute take.

Unlike the strain Quinlan beat out of him in the 1930s, or that got him dropped from Columbia in the 50s, the strain to understand the constants of the American songbook while his own life and body changes is a strain that lures the populous. It is a strain that kept him relevant when many of Quinlan’s other gifts left him. In the Fukuoka Dome, his entire set is a battle to sing in the face of his own decay, to spite the ossified cartridges in his larynx, his striated throat and his perforated breath.

And the old man is in luck, because pop listeners very often concede that all voices, even great ones, must loosen and shrink. This admission is what separates the popular contract from the classical one. For us, a performer chasing down the heartbeat of a song is always welcome, as Sinatra was, to keep pushing himself. That push cannot be set upon a body like the five fixed faces of “Tips.”

And though the smoothness Quinlan taught young Sinatra is welcome and crucial, it is this struggle for proof that we strained to hear: the sixty-round live bout of Sinatra rising from the mat, sneering, and then hitting the core of our favorite songs with a tightened fist and an open heart.


ART: Jenn Brehm, Jason Polan,
Grant Willing

FICTION: Kirby Johnson, Anjali Sachdeva, Chad Simpson, S. E. Smith

NONFICTION: Laura E. Davis, Aaron Gilbreath, Alexandra Kimball, Elena Passarello, Alison Stine

POETRY:Samuel Amadon, Will Arbery, Elizabeth Arnold, Melissa Broder, Kara Candito, John Lee Clark, Graham Foust, Kit Frick, Paul Killebrew, Kyle McCord, Shane McCrae, Geoffrey G. O'Brien, Sandra Simonds, Bruce Smith

ET CETERA: Flannery O'Connor Soundboard, Poetry Bingo

00:00 / 00:00
00:00 / 00:00

A clip from the Looney Tunes / Merrie Melodies cartoon "Swooner Crooner," Warner Brothers Pictures 1944. Excerpted from http://www.youtube.com/watch?v=Whi0b1ZEoa0, August 2012.

00:00 / 00:00

Jennifer Holliday performs "And I Am Telling You I'm Not Going" at the 1982 Tony Awards. Excerpted from http://www.youtube.com/watch?v=rtnKI3ztz9w, August 2012.

00:00 / 00:00

Jennifer Hudson performs "And I Am Telling You I'm Not Going," as adapted for the 2006 Paramount Pictures film Dreamgirls. Live video clip excerpted from http://www.youtube.com/watch?v=UrZTg-0Ozn0, August 2012.

00:00 / 00:00

Jerry Lee Lewis performs "Whole Lotta Shakin' Goin' On" on The Steve Allen Show, 1957. Excerpted from http://www.youtube.com/watch?v=8yRdDnrB5kM, August 2012.

00:00 / 00:00

Buddy Holly and The "Chirping" Crickets perform "Peggy Sue" on Arthur Murray Party, December 29, 1957. Excerpted from http://www.youtube.com/watch?v=WQiIMuOKIzY, August 2012

00:00 / 00:00

Frank Sinatra sings "Strangers in the Night" at the Fukuoka Dome, Japan, December 1994. Excerpted from http://www.youtube.com/watch?v=MMY3HATbdvw, August 2012.


1.   Sinatra, Frank and John Quinlan: Tips on Popular Singing. Embassy Music Corporation. New York, 1941. Accessed December 1, 2011, c/o "Jazz Singers": http://www.jazzsingers.com/TipsOnPopularSinging/.


2.   Tommy Dorsey and His Orchestra, with Frank Sinatra and The Pied Pipers: "I'll Never Smile Again," Victor Records, 1940. Excerpted from The Best of Tommy Dorsey and His Orchestra. Curb Records. Burbank, CA. 1991.


3.   Jolson, Al with music by Ray Henderson and lyrics by Sam M. Lewis and Joe Young: "I'm Sitting on Top of the World (Just Rolling Along)." 1925. Excerpted from The Very Best of Al Jolson. Hammard Records / MCA Records. 1977.


4.   Durante, Jimmy with lyrics by Ben Ryan: "Inka Dinka Doo." 1934. Excerpted from Inka Dinka Doo. Pegasus. 2004.


5.   Prima, Louis with lyrics by Roger Graham, Irving Caesar, and Julius Brammer, and music by Spencer Williams and Leonello Casucci: "Just a Gigolo." 1956. Excerpted from The Very Best of Louis Prima. Prism Platinum. 2005.


6.   Cab Calloway and His Orchestra: "Minnie the Moocher." 1931. Excerpted from Best of Cab Calloway. Hallmark. 1999.


7.   Tommy Dorsey and His Orchestra, with Bob Eberly, lyrics by Lorenzo Barcelata and Bob Russell, music by Lorenzo Barcelata: "Maria Elena." Decca Records, 1941. Excerpted from Best of the Swingers. Chacra Music Licensing. 2006.


8.   Tommy Dorsey and His Orchestra, with Jack Leonard, lyrics by Oscar Hammerstein, music by Jerome Kern: "All the Things You Are." 1939. Excerpted from The Homefront, 1941-1945. RCA Victor / BMG Music. 1998.


9.   Sinatra, Frank and Dagmar, lyrics and music by Dick Manning: "Mama Will Bark." Columbia, 1951. Excerpted from The Frank Sinatra Duets. Svetlana Novojilova Shulguina. 2012.


10.   Crosby, Bing: "Too-Ra-Loo-Ra-Loo-Ral (That's an Irish Lullaby)." 1944. Excerpted from Bing Crosby's Gold Records. MCA Records. 1997.


11.   Sinatra, Frank with lyrics by Sammy Cahn and music by Jimmy Van Heusen: "All the Way." Maraville Music Corporation, 1957. Excerpted from The Complete Capitol Singles Collection. Capitol Records. 1996.


12.   Looney Tunes / Merrie Melodies: "Swooner Crooner," directed by Frank Tashlin with music by Carl W. Stalling and story by Warren Foster. Warner Brothers Pictures, 1944. Excerpted from http://www.youtube.com/watch?v=Whi0b1ZEoa0, August 2012.


13.   Sinatra, Frank with lyrics by Paul Anka: "My Way." Reprise Records, 1969. Excerpted from The Frank Sinatra Collection. Frank Sinatra Enterprises. Burbank, CA. 2008.


14.   Holliday, Jennifer with lyrics by Tom Eyen and music by Henry Krieger: "And I Am Telling You I'm Not Going," from the original Broadway production of Dreamgirls. Video clip from the 1982 Tony Awards, c/o The American Theatre Wing. Excerpted from http://www.youtube.com/watch?v=rtnKI3ztz9w, August 2012.


15.   Hudson, Jennifer with lyrics by Tom Eyen and music by Henry Krieger: "And I Am Telling You I'm Not Going," as adapted for the 2006 Paramount Pictures film Dreamgirls. Live video clip excerpted from http://www.youtube.com/watch?v=UrZTg-0Ozn0, August 2012.


16.   Little Richard, with lyrics and music by Robert Blackwell and John Marascalco: "Rip It Up." Specialty Records, 1956. Excerpted from Here's Little Richard [Remastered & Expanded]. Concord Records. 2012.


17.   Lewis, Jerry Lee with lyrics and music by Dave Williams and James Faye Hall: "Whole Lotta Shakin' Goin' On." Sun Records, 1957. Excerpted from The Definitive Collection. Hip-O Records. 2005.


18.   Holly, Buddy and The "Chirping" Crickets: "That'll Be the Day." Brunswick Records, 1957. Excerpted from The "Chirping" Crickets. MCA Records. 2004.


19.   Holly, Buddy and The "Chirping" Crickets: "Maybe Baby." Brunswick Records, 1957. Excerpted from The "Chirping" Crickets. MCA Records. 2004.


20.   Holly, Buddy and The "Chirping" Crickets: "Everyday." Coral Records, 1957. Excerpted from Buddy Holly Memorial Collection. Geffen Records. 2009.


21.   Lewis, Jerry Lee with lyrics and music by Dave Williams and James Faye Hall: "Whole Lotta Shakin' Goin' On," as performed on The Steve Allen Show, 1957. Excerpted from http://www.youtube.com/watch?v=8yRdDnrB5kM, August 2012.


22.   Holly, Buddy and The "Chirping" Crickets: "Peggy Sue," as performed on Arthur Murray Party, December 29, 1957. Excerpted from http://www.youtube.com/watch?v=WQiIMuOKIzY, August 2012


23.   Sinatra, Frank with lyrics by Paul Anka: "My Way." Reprise Records, 1969. Excerpted from The Frank Sinatra Collection. Frank Sinatra Enterprises. Burbank, CA. 2008.


24.   Tommy Dorsey and His Orchestra, with Frank Sinatra: "When You Awake." RCA Victor, 1941. Excerpted from The Voice of Frank Sinatra. Columbia/Legacy Records. 2003.


25.   Sinatra, Frank with lyrics and music by Sammy Cahn and Jimmy Van Heusen: "Only the Lonely." Capitol Records, 1958. Excerpted from Frank Sinatra Sings for Only the Lonely. Capitol Records, 1998 / 2004.


26.   Rodgers, Jimmie: "Blue Yodel No. 2." 1928. Excerpted from Blue Yodel: His 52 Finest. Nimbus Records. 2009.


27.   Robinson, Smokey and The Miracles: "Ooo Baby Baby." Motown / Tamla Records, 1965. Excerpted from The Ultimate Collection: Smokey Robinson & The Miracles. Motown Records. 1998.


28.   Sinatra, Frank with lyrics by Charles Singleton and Eddie Snyder: "Strangers in the Night." Reprise Records, 1966. Excerpted from Nothing But the Best: The Frank Sinatra Collection. Frank Sinatra Enterprises. Burbank, CA. 2008.


29.   Sinatra, Frank with lyrics by Charles Singleton and Eddie Snyder: "Strangers in the Night," as performed at the Fukuoka Dome, Japan, December 1994. Excerpted from http://www.youtube.com/watch?v=MMY3HATbdvw, August 2012.


30.   Sinatra, Frank with lyrics by Hal Shaper and music by Hal Shaper and Antonio De Vita: "Softly, as I Leave You." Reprise Records, 1964. Excerpted from Nothing But the Best: The Frank Sinatra Collection. Frank Sinatra Enterprises. Burbank, CA. 2008.


31.   Sinatra, Frank: "I'm a Fool to Want You." 1957. Excerpted from Where Are You? Capitol Records. 2002.