The Art of Hardly Trying: Dean Martin’s 60s Swing

Dean Martin Essay - Kiss Me, Stupid Movie Film

This Dean Martin essay contains spoilers for the American entertainer’s 60s filmography. Check out VV reviews, along with cast/character articles, streaming guides and complete soundtrack song listings, at the home page.


Dean Martin and Jerry Lewis emerged as the definitive double act of the 1950s, but as the decade progressed, the tensions between the American entertainers had begun to cast a pall over the duo’s onscreen exploits. Martin became increasingly frustrated at the plaudits his partner was garnering for the grandstanding antics which drew the eye of both critics and audiences (though Lewis would always sing the praises of his straight man for allowing him to reach such goofy heights, averring that, “I can honestly say that I’d have been nothing without Dean.”) For Martin, having his contribution continually obscured by Lewis’ mammoth slapstick shadow had become an onerous chore. The tensions grew throughout the filming of Three Ring Circus (1954), and came to a head with Hollywood or Bust (1956), which was their final film together. By this point, Lewis had begun to conceive of himself as a comedic auteur, a posture which pleased neither Martin or director Frank Tashlin, with whom Lewis clashed openly on set. Lewis likened the end of the partnership to a divorce between two people who hated as hard as they loved; Martin did not share Lewis’ sentimental interpretation of their pairing, telling Lewis, “You can talk about love all you want. To me, you’re nothing but a fucking dollar sign.”

In many ways, Martin was the architect of his own malaise; he’d cultivated the persona of the amiable drunk who shambles his way through life, and many were happy to take him at face value. A reviewer for the Los Angeles Times described Martin as “the world’s laziest superstar.” But countless co-stars attested to Martin’s professionalism — Anthony Franciosa, his co-star in Career (1959), explains that “He never revealed how hard he was working… he made it seem like it was kind of an effortless thing, and he was very relaxed about it.” Everything was going on below the louche, lackadaisical surface, and few would be granted access to Martin’s inner world, repelled by a barrage of willful tastelessness and studied self-deprecation. Martin’s solo acting career nearly ended before it began after the disastrous romantic comedy Ten Thousand Bedrooms (1957), but his redemption began with a string of gems — The Young Lions (1958), Some Came Running (1958) and Rio Bravo (1959) — that established him as something more than a charming crooner and comedic oddity as a turbulent and triumphant new decade began.

Dean Martin Essay: Related — The Irresistible Bulldozer: Judy Holliday’s Brief Comic Swing

Dean Martin Essay - Rio Bravo Movie Film

The Rat Pack represented an expression of Las Vegas at the height of its tawdry chic. It was what Nick Tosches describes as “the holy city of old-guard cool.” But Martin’s relationship with the group was always ambivalent — Dino Crocetti grew up in Steubenville, Ohio, among actual gangsters; he understood the life as something more than it was depicted on the screen. As close as anyone could get to the ever-aloof Martin, it was an opportunity to belong to his own gang; an insurance policy in a business with few guarantees; a swish podium from which to propound the old values that formed him. But Martin never approached his obligations with same gusto as some of the other signatories. He grasped that it was just another racket. Martin had no illusions about the Chairman of the Board, regarding Frank Sinatra as a petulant brat who needed his ego bolstered by those in his orbit, something Martin was unwilling to do. But in the early 60s, Martin was content to don the costume and walk in formation with the pack, joining Sammy Davis Jr., Joey Bishop and Peter Lawford as one of Sinatra’s handpicked hellraisers.

Ocean’s Eleven (1960) has become a byword for the classic cool that the Rat Pack embodied. In retrospect, however, it feels like an exercise in myth creation, laying the table for the decisive victory of pop culture politics. Sinatra and his coterie became indistinguishable from John F. Kennedy’s Camelot, selling a glamour that drew its allure from the power it projected. The Rat Pack were the harbingers of a true celebrity power structure, leveraging their public profile to muscle into the exalted circle. But for Martin, politics was just another racket he kept at arm’s length; he had no illusions about what either Sinatra or Kennedy were selling to America, and his attitude shines through in his contributions to the three films the Rat Pack made together in this period of possibility and hubris. All three productions feature hungry upstarts trying to stake a claim to the riches that are there for the taking. In Ocean’s Eleven, they are a group of World War II veterans who plan an audacious raid on five Las Vegas casinos on New Year’s Eve — former commandos who plan to use some of “those neat little tricks” the army has taught them.

Dean Martin Essay: Related — Know the Cast & Characters: ‘Triangle of Sadness’

Dean Martin Essay - Ocean’s Eleven Movie Film

Martin plays Sam Harmon, a singer who drifts in from Hawaii to administer some “mother love” to the monomaniacal Danny Ocean (Sinatra). Part of Harmon relished the opportunity to shrug off the island torpor and bring some of the old esprit de core into civilian life, but he can never quite overcome his ingrained cynicism, he never dares to hope that the victory dividend they are seeking is attainable. Where Ocean drives events forward, Harmon is happy to flow, describing himself as “a very manly sloop,” carried on a tide of his own appetites and desires, content to vamp on the piano while the plot unfolds in the foreground. There are moments when it feels like Martin is being actively wrangled through a scene; his wry amusement sets him apart from “tough guy” actors like Richard Conte and Henry Silva, who don’t seem to have grasped that the whole exercise is a self-serving lark, an assault on the culture’s sensibilities. When Harmon performs ‘”Ain’t That a Kick in the Head” at the Sahara on the night of the robbery, it is playacting with a hidden motive; he woos the audience for his own purposes. It’s necessary to be in that moment. But there is something elusive in the seduction routine, he has no fidelity to anything but the haul. The singer tells Shirley MacLaine’s drunken reveler that “I used to be Ricky Nelson. I’m Perry Como now.” Like Martin, Harmon grasps that the racket requires a perpetual flexibility towards how one chooses to be defined.

Dean Martin Essay: Related — Soundtracks of Cinema: ‘Women Talking’

The darkness is never far from the surface. Harmon confesses that he is half the man he was in 1945, and when Jimmy, Lawford’s pampered rich boy, talks of turning his money into power, Martin’s character lays out his political program: to “repeal the 14th and 20th amendment, take the vote away from the women, make slaves out of them.” Given how much Ocean’s Eleven feels like an extension of the act the Rat Pack performed by night at the Sands, Harmon’s statement is a troubling window into exactly what the crew’s carefree masculinity entailed. Ocean’s Eleven conceives the casino as an American battleground, with the rubes who are lured in by the hospitality, and those who are hip to all the angles. Garbage becomes indistinguishable from gold in the scramble to prevail, and Martin is perfectly at ease with this confusion; it is the perfect backdrop for his winningly dissolute, engagingly tasteless sensibility. For all its vitality, Ocean’s Eleven ends on a downbeat note: the big jackpot has eluded the main players, and though they are at the height of their cool, the final scene — cribbed by Quentin Tarantino for Reservoir Dogs (1992) — finds them walking the streets in the unforgiving light of a Vegas morning. The vainglory that buoyed the caper has melted into a recognition that nobody stays on top forever.

Dean Martin Essay: Related — Mystical Ennui: Peter Cook at a Distance

Dean Martin Essay - Ocean’s Eleven Movie Film

The gang transferred from one frontier to another in Sergeants 3 (1962), an uninspired John Sturges Western in which Martin plays cavalry officer Sgt. Chip Deal. Again, there are more manly pursuits unencumbered by meddling dames — Deal and Sinatra’s Sgt. Mike Merry conspire to free Lawford’s Sgt. Larry Barrett from the bonds of matrimony and its concomitant responsibility and keep him in the army. The film underlines the importance of having a crew of one’s own, one that transcends the accepted power structure and adheres to its own code. The law enforced here is one of creative cruelty; those with the decisive edge offer punishment of a certain kind, an errant breed of authority refracted through their personal magnetism. Martin’s contribution has none of the pathos he brought to Rio Bravo, but he proves himself to be one of the screen’s great reactors. Some of the actor’s best moments take place on the margins of the frame; he is able to enliven a scene with the slightest of gesture, coded with audience complicity and self-awareness. Martin could not overcome who he was if he tried, and he never did. Martin enters with a cigar clamped in his mouth, clasping a hand of cards and a drink, smirking his way through a riotous bar fight; he stops in at the Lonesome Bar when he should be on patrol, knocking back a glass of “licker” and letting a look of existential sorrow wash over his face. It is the only moment where something true threatens to penetrated the film’s blasé veneer.

Bishop’s uptight Sgt.-Maj. Roger Boswell decries the “sloppiness” of the cavalry’s operation, but it is intrinsic to being a part of this army. A forcefield of mockery and merriment keeps the vicissitudes of the world at bay, the soldiers chase after a never-ending adventure with ‘”no leaders” and “no chain of command.” Deal yearns to embark into the wild expanse, to “blow this mausoleum” and grab a chunk of the action that awaits in the “unknown country” at “the end of nothing.” An army of one’s brothers must fight on the frontier of wild pursuits, staring over the precipice of irrelevance. Once a soldier, always a soldier. The lifestyle leaves its imprint, which comes into sharper focus in the lightweight gangster musical Robin and the 7 Hoods (1964). The barbarities of the lifestyle pass into posterity and finally become fit for pastiche, ready to be blunted by song; the old killers develop the capacity to laugh at their former brutality; the old empires are usurped by something more outwardly respectable, deigning to lend the past a heroic patina. By the time of Robin and the 7 Hoods, the old struggles are a memory, the old campaigns have passed into myth. Now there are new strains to deal with — stardom, wealth and cultural clout. While Martin’s friends bore these burdens with all due gravity, he never lost sight of the absurd station that he occupied, and the undue reverence it engendered.

Dean Martin Essay: Related — Soundtracks of Cinema: ‘Sharper’

Dean Martin Essay - Robin and the 7 Hoods Movie Film

The gangster character had hit a pitch Martin could jive with — derisive, sardonic, a parody of itself — and he seized on its newfound grotesquerie. Sinatra is in his element as Robbo, aping pals and fixers of old, and Davis Jr. is happy to tag along as Will, but as the “loose and easy’ pool hustler who “blew in from Indiana,” Martin’s Little John just wants to play it cool and goose up the action. In a film of outsized performances, Martin’s game is one of small gestures that bring the whole thing into disrepute; he moves at his own rhythm, appearing a step off but actually drawing the eye amongst the gallery of stars. While Davis Jr.’s song “Bang! Bang!” goes full-tilt, Martin gently croons “Any Man Who Loves His Mother” over a game of pool. And although he is clearly having the time of his life singing with Bing Crosby on “Style” — the joy is etched on his face — it is one of the few moments of genuine abandon in his screen life. Some of that old Steubenville grit comes through in the tough guy cadences, but Little John is essentially a figure who feels thwarted by the overbearing presence of Sinatra’s Robbo, and allows himself to be led astray by his own appetites — art stumbling onto the stage and doing a cruel impersonation of life. 

Robin and the 7 Hoods seeks to dramatize the creation of folk heroes, yet it eulogizes the streets while looking down from the penthouse. By this time, Steubenville or Hoboken were as much a playground of imagination as 60s Vegas, Prohibition-era Chicago or the Old West. Martin was attuned to the contradiction and was never inclined to indulge it; he never tried to retain his ties to the old life of bookies and back rooms — it never held any romantic charge. As the gang had fun with the past, the future was nipping at their heels. In an echo of Ocean’s Eleven, Robin and the 7 Hoods ends in failure: the hoods have been undone by the old power structure, reduced to tramping the streets and singing for their suppers once again. But the timing seems all the more poignant in this instance. By the time Robin and the 7 Hoods was released, The Beatles had already made their first appearance on The Ed Sullivan Show; new cultural currents were emerging which threatened to unseat the Rat Pack from the pinnacle of cultural supremacy. As Robbo’s operation is brought down by popular fervor, as they abandon their gambling joint to the sledgehammer wielding agents of moral indignation, Sinatra’s character tells his crew that “I can’t fight the people,” and they flee by the fire escape. The public cannot be assuaged, and their judgement is summary.  

Dean Martin Essay: Related — Soundtracks of Cinema: ‘The Fabelmans’

Martin would sink deeper into himself, becoming an increasingly distant figure, content to tread the path of least resistance. He absolutely refused to take his craft seriously by declaring, “They say this is hard work, this acting. What bullshit… it’s easy work. Anyone who says it isn’t never had to stand on his feet all day dealing blackjack.” The persona Martin had so carefully crafted became a reliable (and lucrative) crutch, but in the right hands, it could be put to incendiary effect, most strikingly in Kiss Me, Stupid (1964), in which Billy Wilder took Martin’s public profile right to the edge of what was permissible. He is simply Dino, first seen performing at the Sands and informing the audience that he is returning to Hollywood to shoot a new movie with the Rat Pack and to record a television special with Bing Crosby. Wilder gives Martin free license to flex his roving eye and sly tongue, every inch the drunken womanizer of the popular imagination. But one gets the impression that this is just another Martin put-on, that in appearing to betray something of himself, he is actually adding a further layer of mythology to the mix. Dino may be no closer to the center of the man than any of the roguish characters he portrayed on the screen, a comfortable spin on the reality.

Dean Martin Essay: Related — Recovery, Survival and Extinction: Abel Ferrara’s Exile Cycle

Dean Martin Essay - Kiss Me, Stupid Movie Film

Dino has to take a detour in the desert and winds up stuck in Climax, Nevada, where his car is sabotaged by two struggling songwriters, Orville (Ray Walston) and Barney (Cliff Osmond), who hatch a plot to prey on Dino’s reputation as “a sex maniac” and sell him some of their compositions. They enlist the services of a cocktail waitress known as Polly the Pistol (Kim Novak) to pose as Orville’s wife and woo Dino, in exchange for the chance to play him some of their songs. Wilder’s ribald farce gets substantial mileage out of the legend: Dino is a fox let loose in the henhouse, a savage sybarite from the wilds of the entertainment jungle who invades the domestic front, a slick sexual assassin who is constantly in pursuit of the “action.” Dino informs Orville that “it’s a habit with me, like breathing.” Polly is the red meat dangled in front of Dino’s nose, the sacrifice to the gods of showbiz success. Wilder and co-writer I.A.L. Diamond document the narcotic effect of star power, how a small sprinkle of stardust can grow into a world of illusion with its own moral gravity. Martin dwelt in the depths of his persona, but this agent of chaos is one who finds his powers waning; he is stuck between Ricky Nelson and Perry Como. Wilder and Diamond’s script broaches some of Martin’s insecurities — when The Beatles are brought up, Dino quips, “I can sing better than all three of them,” to which he is reminded that “they’re young and they’re popular” and “you’re over the hill.” The “big Hollywood hotshot” is unsure of his place in the firmament as new stars begin their ascent.

The second half of the decade became a period of adaptation for Martin. He made a play for the burgeoning spy thriller market with The Silencers (1966), a tongue-in-cheek James Bond knockoff which spawned a franchise. The film is perhaps best known now for one of its sequels, The Wrecking Crew (1968), co-starring Sharon Tate and being featured in Once Upon a Time in Hollywood (2019). Martin plays Matt Helm, an international playboy and photographer who also happens to be on the payroll of Intelligence and Counter Espionage (ICE), and averts global annihilation in between bedding multiple women and drinking heavily. Bond’s casual sadism gets an added layer of dissipation with Martin’s heavy-lidded delivery; he hits all the notes the material requires, a relaxed register that bespeaks a world of danger and decadence, with a sleepy intonation and some well-placed slurred words to set the mood of salacious hijinks and casual misogyny. Martin is heavily tanned and clammy, lapsing into fleshy self-parody as he gives knowing looks to the camera, as if to say to the audience, “There’s no easier racket than this.” Like Martin, Helm is an agent of the status quo, he strives to uphold the old order at a time when it is being challenged on multiple fronts. Martin’s quest for exponential action has become a matter of self-preservation, in which sex is reduced to a game of control.

Dean Martin Essay: Related — Soundtracks of Television: ‘Liaison’

Dean Martin Essay - The Wrecking Crew Movie Film

There were always the Westerns. The Western represented a refuge for Martin, somewhere unbeholden to the cruel whims of public approval. Although the genre was in a state of flux as it entered the 60s, with films like The Man Who Shot Liberty Valance (1962) planting the seed of doubt that would grow into the thoroughgoing dismantling of the myth in The Wild Bunch (1969). As Martin churned out lackluster Matt Helm sequels and sleepwalked through anemic sex comedies, he did much of his best work in Westerns. The actor’s performance as inveterate gambler and repentant heel Tom Elder in The Sons of Katie Elder (1965) ranks amongst his very best; full of pathos and vigor, it is a deftly executed evocation of regret, rage and redemption. Martin and John Wayne make a fine duo as estranged brothers, perfectly cast as men for whom time is slowly running out and the race for a legacy is gathering pace, fighting back against the relentless momentum of change. The theme of dispossession — the four Elder brothers struggle to regain control of the family ranch — chimes with the cultural temper of the time, charting a growing generational tension that is only heightened by the presence of future New Hollywood idol Dennis Hopper. The Sons of Katie Elder details the fight for control of a town, and it is not difficult to see Duke and Dino’s exertions as an attempt to signal their enduring viability as leading men, to carve out a tenable future for themselves.

Dean Martin Essay: Related — Know the Cast & Characters: ‘1923’

Martin would tussle with another young gun in Texas Across the River (1966), a lightweight romp in which his grizzled gunslinger teams up with a Spanish duke played by Alain Delon — a new breed of sophisticated, sensual star whose work in European art cinema would endear them to the film school generation. Martin is at his most rumpled, becoming accustomed to wearing his age, while Delon is out of his element, unable to make the best of the less than stellar material which his co-star manages to at least have some fun with. Whatever the role, Martin always seemed at ease on the frontier; the demands of being Dino would evaporate and he could lose himself for a moment in the vastness of the terrain. But the landscape was shifting under Martin’s feet, and Rough Night in Jericho (1967) signaled that the clearcut morality of Tom Mix had given way to the ambiguity of Sergio Leone. Not that Martin would ever have approached his work on such terms, but his portrayal in of ex-lawman turned local power broker Alex Flood could be read as a deconstruction of the Dino act. Flood’s languid manner and ironic smile conceal a gambler’s ruthless eye; he is the carefree wolf in sheep’s clothing, wearing a tarnished white hat. The apparent effortlessness was always a ruse, and age hardened it into something more confrontational. By 1967, the blood was on display; the bar fights had lost the playful swagger of the days when the Rat Pack set the tone. As the 70s dawned, survival for Martin became a matter of staying on the horse and waiting for the culture to loop back in his favor, to mature into the venerated relic who had come direct from the bar.

D.M. Palmer (@MrDMPalmer) is a writer based in Sheffield, UK. He has contributed to sites like HeyUGuys, The Shiznit, Sabotage Times, Roobla, Column F, The State of the Arts and Film Inquiry. He has a propensity to wax lyrical about Film Noir on the slightest provocation, which makes him a hit at parties. The detritus of his creative outpourings can be found at waxbarricades.wordpress.com.

Dean Martin Essay: Related — The Western Enters the 70s – Part 1: Sam Peckinpah’s Lonely Cowboy