Steve Jobs and Frank Sinatra: One destroyed a visual art-form, the other elevated it

Steve Jobs’ last words, it’s claimed, were, “Wow! Wow! Wow!,” ensuring that right up till the very end, none would dare label him non-enthused. What a salesman — still generating excitement for his products with his literal last breath. That conclusion might assume that he shuffled off this mortal coil, still pitching his favorite ‘80s musical act, Bow Wow Wow, available in the form of 99 cent downloads on iTunes, and the assembled witnesses just happened to mis-hear.

Speaking of iTunes, for all the eulogizin’ and wailin’ and breast-beatin’ over the death of Mr. Jobs, I’ve yet to hear anyone acknowledge his role in obliterating a significant 20th Century art-form, namely the record album cover.

It’s true that album covers have been on the way out since 12-inch LPs were downsized to CDs and cassettes — but it was Jobs who unleashed iTunes, and brought down the curtain on the days of music-as-packaged-goods.

Voormann's revolutionary 'Revolver' design -- an art-form made extinct by Steve Jobs

And, therefore, it was Jobs who took away the jobs from geniuses such as Dean O. Torrence, who started out warbling as the junior partner in Jan and Dean, and later became a pre-eminent designer of album cover art, through his firm, Kittyhawk Graphics. It was Jobs who might just as well have smashed the knuckles of Klaus Voormann, creator of the visuals on the Beatles’ “Revolver” LP. Perhaps Jobs didn’t exactly strut into the Rijksmuseum or the Musée d’Orsay, and spritz lighter-fluid over the displayed treasures, but that’s only because every vandal works to his own modus operandi.

The death of Jobs, coinciding with the rise of cloud computing — now, there’s a symbolic image that just begs illustration by a neo-Raphaelite — caused me to consider the rich heritage of the album cover, as a now-defunct art-form. Everyone seems to have their favorite cover, and it’s nearly always the Andy Warhol commission for the Velvet Underground and Nico LP (aka, “the Banana Peel cover”), the functioning trouser fly on the Rolling Stones’ “Sticky Fingers”, or that grossly overrated, committee-determined pastiche that is the fold-out cover of “Sgt. Pepper’s Lonely Hearts Club Band.”

I would disagree. I say that a standard of graphics excellence was established by the Chairman of the Board, Mister Frank Sinatra, through the design of the jacket on his 1966 Reprise Records release (FS 1020), “That’s Life.”

I say further that the design of this album cover has never been surpassed, and it will remain eternally the ne plus ultra of the genre.

That's Life, baby: The greatest LP cover of all time

Where, you may demand, is the evidence to support this bold claim? Let’s begin with an examination of the title. The dominant element is typographical, deploying an Egyptienne Bold typeface, with the artist’s name rendered in an outline font, with the album title in a cyan-filled variant below. The color choice of cyan accentuates the mood of defiant cool that overwhelms the title track (exemplified by that tune’s familiar extended Hammond-organ introduction, performed by Michel Rubini.) We take note of the close-kerning, and the virtual absence of leading between lines, which creates a flow-together effect that unmistakably associates Old Cyan Eyes with the message of the title. Four words, one copy-block: FRANK/SINATRA/THAT’S/LIFE. The resulting conclusion can only be, here is Sinatra; here, inextricably, daddio, Life follows, Life in the only form we would ever wish to recognize. Cocktails. Cocktail waitresses. Rascally companions to join you in teasing the cocktail waitress. Late hours, a phone number scribbled on a cocktail napkin, and someone in the dim distance playing a Jimmy Smith tune on the Hammond B-3. So, set ’em up, Joe. It is Joe, right?

FRANK/SINATRA/THAT’S/LIFE. Those are some powerful four words that can effortlessly evoke such a bacchanalian scene. Try adding just two more words, and you’d surely wind up in a gurney, awaiting a liver donor.

The secondary element is the pseudo-expressionist illustration, by an uncredited artist. On first glimpse, this seems like a typical mid-1960s pastel-stick execution following the fashion of the time. This is the halfway point of Modernism en route to becoming Pop Art. Peter Max has yet to attract any notice beyond a couple of blocks in the nascent East Village, and Leroy Neiman and Andy Warhol are not yet warmly received by their bank managers. But in 1966 the successful post-war commercial artist cleaned and put away his brushes, reached toward the oil-crayons, and learned the techniques of the forcefully applied smudge to canvas. What is implied through the pastel blur is a world finally gaining momentum on the declining side of mid-century, with the population engaged in gassing up their little Honda motor scooters, and wondering if it was too early to reserve hotel rooms for Expo 67.

Men with hats and amalgamated teeth, going places, mid-century

Mrs. Irma Councill was the most prolific and best-known Canadian working in this pseudo-expressionist genre, and for a time you saw her work everywhere. Her portraits of business moguls, politicians and hockey players were published in Weekend and The Canadian magazine, and it may have been her artistic approach that influenced period advertisements for the Meteor Montcalm, Macleans toothpaste, and Inglis appliances. Or else it was another crayon-wielder with reductionist tendencies, about to feel the hot breath of psychedelia charging in close from behind.

Was our Mrs. Councill the anonymous illustrator who painted Frank for “That’s Life?” Or — here’s an odd thought — was it Frank hisself who commissioned and undertook the work, as a self-portrait? It is known (through an episode of the Dick Van Dyke Show) that Sinatra painted recreationally in the Modernist style. Could it have been none other than the Chairman who is responsible for depicting himself as the distorted gargoyle who appears on the cover?

Whoever had the task of slapping pigment on medium, it was someone who saw the singer clearly, knew him well, and didn’t much like him.

Out-of-proportion headgear

The chapeau is the key element, recognizable from previous images of Frank, but here displayed out-of-proportion, with a tumefied hatband that could be taken, in a current context, as a gang-banger’s colors, or, from a timeless perspective, as a pirate’s bandanna. Why the giant lid? Through the late 1950s and early ’60s, the Chairman used fedoras to rakishly conceal his advancing male-pattern alopecia, and this great big hat nicely suggests a coming acceptance of the “I, Claudius” hairpiece he would begin to affect at the earliest point in the 1970s.

Suggestive sniffer?

Yet, here the shocking volume of the hat accounts for fully forty per cent of the composition of the head. Sombreros may take on these dimensions, or a Stetson worn whimsically, but never a hipster’s fedora. The explanation, as I see it, is that in the artist’s view, the headgear must form a convenient metaphor for male potency. This is a fully engorged noggin, and the artist has freely borrowed a pint of devilry from the caricature of “Mr. Punch” that appeared on the cover of the mid-1800s editions of the British humor weekly. And as is the case with Punch, there is something vaguely kinky about the way Ole Blue Eyes’ nose is drawn, a visual pun that should make normal people feel squeamish.

Having courted and won the television starlet Mia Farrow, who was half Frank’s age on their wedding day, Blue Eyes is seen through the artist’s eye as a satyr who is entirely self-delighted with his own extended capacity to pull hippie broads. The picture fairly cries, “Ring-a-ding-ding!”, with all the unspeakable connotations that phrase delivers.

The Chairman needs a rest

Frank was 51 when he waxed these sides, not necessarily a terrible age for a male, but a trying time for the self-styled Lothario. And, make no mistake, he was a terrible male, a surly survivor of a lifetime of bad behavior. The mid-stage Frank who could philosophize, “That’s life,” was a man entering his Pantaloon Years, the time of becoming an aging buffoon. A slender, handsome youth, known as The Voice, (nidus of swooning post-war bobbysoxers), Frank now appears well along the way to becoming hideous. His debauched expression, the pouchy eyes, the newly-forming jowls, all offer the visage of a roué who began his Las Vegas mornings in mid-afternoon, consuming what was reported to be his favorite breakfast: scrambled eggs eaten from the chest of a hooker.

Dental work projected toward your throat

The artist stylized the Sinatra smile, again appropriating the manner of the mid-century airline advertising illustration. His teeth are streamlined into a smoothly amalgamated band of white, in perfect contrast to the icy blue hatband. The teeth balance against the declaration of his name. The symmetry invokes mild terror in the viewer, as “FRANK/SINATRA” and his exposed teeth seem to be projecting from the album cover, and into your exposed throat. That’s how thin is his veneer of affability. Do not be deceived by the aging Pantaloon with the tired, but defiant eyes, this sad old dandy, costumed for the preceding decade, with the new young wife we all know he will not be able to hold past a year or two, at most. (His wife during the 1951-7 period, Ava Gardner, had already sized up the Twiggy-like Mia Farrow, and sniffed, “I always knew Frank would wind up in bed with a boy.”) They are lining up to bet against him in the Sands, the Sahara, and the Circus Circus. You two-dollar punters may not see past the Frank-smile, the smooth white-streak of molars, incisors, bicuspids, but that will be at your extreme peril. He is cornered, dangerous. Those capped white choppers — perhaps the best work ever by the very finest orthodontist in Beverly Hills, Dr. Lenny Bloom — will tear the flesh from your face where you stand, no different than if Frank were an alarmed orangutan set off by a moving shadow outside his zoo cage.

What kind of face would instill this type of fear? The journalist Gay Talese makes it crystal-clear in his revealing April 1966 profile of Sinatra, published in Esquire magazine, just as the lithographers were counting their cardboard inventory for the cover of the “That’s Life” album. Unforgettably, Talese recounts the Chairman’s impulse to pick on Harlan Ellison, a formidable figure in the L.A. entertainment community. Frank demands to know what Ellison, who is dressed in Carnaby Street gear, does for a living, and Talese records the ensuing dialogue here:

“I’m a plumber,” Ellison said. “No, no, he’s not,” another young man quickly yelled from across the table. “He wrote The Oscar.”

“Oh, yeah,” Sinatra said, “well I’ve seen it, and it’s a piece of crap.”

“That’s strange,” Ellison said, “because they haven’t even released it yet.”

“Well, I’ve seen it,” Sinatra repeated, “and it’s a piece of crap.”

Now Brad Dexter, very anxious, very big opposite the small figure of Ellison, said, “Com’on, kid, I don’t want you in this room.”

“Hey,” Sinatra interrupted Dexter, “can’t you see I’m talking to this guy?”

Dexter was confused. Then his whole attitude changed, and his voice went soft and he said to Ellison, almost with a plea, “Why do you persist in tormenting me?”

Frankie goes to the Stony Lonesome

In sum, Sinatra arrived on the cultural scene already a bully (see mugshot, left), and, now, at his half-century, he suddenly found himself transmogrified into a square, to boot. This, from the man who is all set to set you straight on what life is: “Riding high in April, shot down in May.”

That’s Life? Sheesh. Frank was precisely one of those crazy adults you’d encounter somewhere, perhaps in your parents’ rumpus room, someone who would seem delighted to tell you all about the many fascinating experiences they’ve had — “I’ve been a puppet, a pauper, a pirate,/ A poet, a pawn and a king” — until you commit the error of trying to get an innocuous word in edgewise, along the benign lines of “Gee, Uncle Frank, you’ve certainly had some interesting jobs in your time,” and then he abruptly snaps and begins shrieking violent gibberish. “Pisherke! What the hell do you know? Hah?” All you can do at that point is walk away with your Hires Root Beer and try not to shrug too visibly while another adult says, “Frank, come on. He’s just a kid. He din’t mean nothin’.”

Yes, Frank belonged to, was the epicenter of, that unknowable Adult Life, into which you had to be out of your mind to peer too closely. Your child’s curiosity might want to know: What kind of songs could come out of someone with that kind of face? But the knowledge could never make sense; not then, not now.

For the music contained within this eternally perfect album-cover is as sorry a collection of schlock as it is possible to imagine. It is mercifully short: a scant 25 minutes of product, spread around 10 tracks. However, it is some crazy material, consisting of two Gilbert Bécaud compositions and one Michel Legrand, leading to the idea that this might have become Sinatra’s great lost Charles Aznavour/Jacques Brel project, if only anyone had thought to invite them. (Click here, if’n you dare, to hear the Chairman sing the album’s title track.)

But the rest of the brief LP is a mish-mash of movie soundtrack tunes (“The Impossible Dream,” “Somewhere My Love [Lara’s Theme”]), interspersed with the truly ridiculous. In the latter category is the Chairman’s take on “Winchester Cathedral,” a novelty record by the New Vaudeville Band that somehow caught on with the kids. The song was originally performed by some teenaged British musicians goofing on the music of their grandparents, a spoof of Rudy Vallee — which was the mannered crap issued on 78 RPM records in the 1920s and ‘30s that Frank’s natural, unaffected style (that is, Bing Crosby’s style, refined with a trace of ethnic flavor), pressed on 45 RPM sides in the 1940s and ‘50s, blew out of the water. The idea of Frank goofing through a version of this oddity could only have been intended by someone wishing to cause him harm: “Vo-vodey-oh-do.”

And, yet, there it is. Sinatra, the famed perfectionist, reduced to the most clueless form of pandering. Outside the studio, the Viet Nam war is the story. Frank’s son and namesake endures a kidnapping. Life magazine explains how the Negros are demanding their rights in the south. JFK is gone; LBJ will not run for re-election. Nixon’s in session with his Manhattan psychiatrist, Dr. Arnold Hutschnecker. Guns are being trained on RFK, MLK. And then Mia’s lawyer tells you she wants a divorce.

No wonder he appears so uncomfortable on the cover. You can read right through the look in his eyes, as interpreted by the illustrator, and know his thoughts: “Are you laughing at me? You’d better not be laughing at me. Christ, they’re laughing at me.”

This is plainly a man on the verge of something, wondering if it makes sense, at his stage of life, to keep tamping down that building force within him — or do you give in to your impulses? Only seven years earlier, he had sung, “Something’s Gotta Give,” and the audiences loved it, but in 1966 it seemed that the end-result of the long period of suppression would be blood running from the nose of some wise-guy Hollywood screenwriter, right down the punk’s ruffled Edwardian shirt. It would take three more years before that force would be unleashed, when the “Life” Sinatra was shouting about in “That’s Life” would veer into a different direction altogether.

That was the end of the ring-a-ding-ding decades, and the birth of his career-shifting LP, “Watertown.” The new release would be sheathed in a very different kind of record cover. Regrettably, that album’s cover-design would scupper the bold new venture, straight from the get-go.

To be continued

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