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THE 33 COOLEST GUYS - PAST & PRESENT
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                               by Harold von Kursk
                                   
   
Cool is as much about attitude as it is about style, looks, or charisma. Any definition of cool immediately begs the question: who gets to define cool?  Because if we borrow from the Heisenberg Uncertainty Principle for a moment, the very presence of the observer alters the observed entities in fundamental ways. Accordingly, the quantum leap we take in celebrating 33 cool cultural icons is itself an absurd exercise, but one which does does serve to draw attention to the elements of cool - the elan vital which separates certain beings from others, and draws us towards them.

As such, this attempt at identifying the most brilliant exponents of cool should be understood as a search for the unmistakable, irrefutable, yet equally elusive properties which inform our vaguely catalysing notion of "cool."  For the essence of cool is in some sense a distillation of everything that is brilliant about life and transcends the drudgery of politics, bureaucracy, rules, and convention.  "Cool" is about breaking barriers, pushing the envelope, and thinking out of the box and living as freely and creatively as one can imagine.

Certainly, there is much we can learn from examining the lives of the cool. We should relish the grand sweep of their approach to life - their charisma, class, taste, independence, and a certain indefinable sense of bearing and style which gave these men a "larger-than-life" quality.

We are confident that each and every member of this ad hoc pantheon of cool fulfills all the vital prerequisites of men who looked beyond convention and chose to creatively define their own path towards identity and marched to their own beat.

Like John Malkovich's character explains to Clint Eastwood in IN THE LINE OF FIRE, we would ask you the reader to join us in celebrating men who "punctuated the dreariness" and present a speculative, evocative, and hopelessly subjective classification of 33 cool "gentlemen" from the past and present.

THE PANTHEON OF COOL

1. FRANK SINATRA

The personification of cool, Frank Sinatra was a man who conveyed more style, presence, and attitude than perhaps any other man alive. Volatile and vindictive, sentimental and soulful, Sinatra was the supreme entertainer of his generation who reached deep into the soul of a global audience.  He brought attitude, style, and at times a melancholy sense of brooding to his music as well as to his film roles. In his private life, Sinatra was a controversial figure who counted mob bosses and killers amogst his closest friends and shared mistresses with JFK and Sam Giancana. Though he attained iconic stature early in his career, he never forget his working-class roots.

A little-known anecdote about Sinatra's sense of honour illustrates why we choose to rank him as one of the coolest of all time: Sinatra would often spend evenings playing poker with friends in the kitchen of Nikki Blair's, the legendary Sunset Strip resto-bar, where he could escape fans and autograph seekers. 


On one such evening, a black waiter accidentally spilled a tray of glasses on the floor.  Nikki Blair, the restaurant owner, fired the man on the spot for having disturbed Mr. Sinatra. Frank, however, had other ideas. He called Blair over to the poker table, grabbed him by the shirt and asked Blair, "Nikki, how much is one of those glasses worth?" "About 5 dollars," replied Blair. Sinatra then told the waiter to break every glass he could find in the kitchen.

After several hundred glasses were broken, Sinatra motioned one of his bodyguards to give him (Sinatra) a thick roll of $100 bills. Frank then handed the roll to Blair and gave the now terrified restaurauteur some chilling advice: "Nikki, this guy can now break as many glasses as he wants for the rest of his life.  And every time I come here, I want to see that he's still working for you. Is that clear?"   

2. SEAN CONNERY

The man who gave James Bond his manhood, Sean Connery served to define the cool, determined, and laissez-faire aura of James Bond, Agent 007. As Bond, Connery set the standard for would-be seducteurs with his roguish manner and cynical elegance.  Connery doesn't need an Aston Martin or nerves of steel at the Baccarat table to assert his particular brand of personal magnetism, however. Over the years, his screen roles have consistently enamoured him to a public that revels in his feline sexuality and wry demeanour. As one of the world's greatest sex symbols, Sean Connery is a resonant and resolute figure of male majesty in an era of increasingly limp and shallow heroes.



3. MARCELLO MASTROIANNI

Italy's great film icon leapt to international fame on the strength of his appearance in Felline's La Dolce Vita, which took world audiences on an insider's tour of Rome's sexy lifestyle.

Mastroianni came to epitomize the cool nonchalance of the emerging European jetset, and in so doing defined the essence of the sophisticated Italian playboy and seducer.  He was a man rarely flustered, a legendary Lothario who bedded virtually every woman he desired. Over the years, his film work captured the grace and aesthetic sensibility of the continental lover. Mastroianni embodied a relaxed and nonchalant approach to the opposite sex which made him all the more desirable. His effortless mastery of the art of seduction ranks him as one of the most charming of European playboys.  On and off the screen, Marcello embodied the devil-may-care spirit of man who loved women far more than himself, making him all the more irresistable as a supreme continental lover.


4.  JOHNNY DEPP

The former poster boy for anti-establishment rebellion, Depp has been steadily evolving from the grungy cool of his twenties when he was drinking himself into oblivion. Today Depp affects a vaguely disaffected, disenchanted, and disinterested stance towards fame, having found happiness in his 14-year relationship with French singer/starlet Vanessa Paradis, and their two children.



He was however the model of bad boy cool for having notoriously trashed hotel suites during his stormy relationship with supermodel Kate Moss.  But Depp has long since abandoned much of his antagonistic persona in favour of a dangerously sexy look, all the while retaining the image of a man who hates authority, orthodoxy, and anything remotely corporate or conformist.

His friendship with Hunter S. Thompson – Depp would incarnate the late American gonzo journalist in the film “Fear and Loathing in Las Vegas” – also earns him considerable cool points for having steadfastly resisted the encroachment of fame in favour of a potent commitment to stand above the bourgeois madness of mass civilization.

5. CHE GUEVARA

The late Cuban guerilla leader is a classic example of revolutionary cool, a man who fought against the corrupt regime of Batista and then expanded the struggle to  Latin America and its tyranny of military dictatorships.  Guevara's image remains a  fixture on the walls of many students whose appreciation of his anti-authoritarian idealism often overlooks his theoretical dogmatism. 

To his credit, however, Guevara broke with Castro over the limitations of their revolutionary ambitions, and believed that Cuba must export its populist brand of Marxism in order to combat the rule of Latin America's military junta. Guevara died waging guerilla warfare in the Bolivian jungle, and will forever stand as a martyr to socialist idealists everywhere.

His life has since been further immortalized in Walter Salles’ 2004 film “Motorcycle Diaries” which saw Gael Garcia Bernal play Che in his early idealistic years and this year’s four-hour “Che” biopic from Steven Soderbergh starring Benicio Del Toro in the title role.  Both films reveal a man of great vision and idealism, and nomatter what we may think of his Marxian politics, Che lived the life of the revolutionary to his last breath in the Bolivian jungle.

6. MARLON BRANDO

Brando redefined the way actors approach their craft with his cryptic macho moodiness and almost feline sensuality. Brando had many imitators, but no one truly captured the force of his personality and quixotic perspective.  He was truly a cult onto himself, seething with rage and railing against absurdity. From On the Waterfront to The Godfather to Last Tango in Paris to Apocalypse Now, Brando cut an
iconoclastic and enimatic figure wherever he trod. There was a dangerous aura to his often brooding or melancholic expression,  and no one will ever be able to forget the pathos of his plaintiff cry of "Stelllaaa!" in A Streetcar Named Desire.

Brando also chose to define his personal life in highly independent terms – buying an island in the Pacific and choosing to reject the false values of Hollywood excess.  Though he was a victim of his own self-destructive torpor – allowing himself to becoming massively overweight as a way of destroying his sex symbol iconography – Brando always fought the brave fight to stay coolly aloof to the moronizing orthodoxies of a plastic world.




7. SAMUEL L. JACKSON

Quentin Tarantino's Pulp Fiction turned Samuel L. Jackson into a bible-spouting, born-again hit man who preached virtue to his intended victims.  His performance alongside John Travolta established a new level of street cool as against the decidedly hateful and violent message of black rappers. Jackson’s stride is more of a sensually stylized strut than a walk, and as Jules, he created a character that was at once defiant, proud, reverential, purposeful, and resolutely cool.

Jackson's hip posturing took an extended turn in Jackie Brown, in which he played a supremely cynical arms dealer spewing chic aphorisms like the following, "You want to have an AK-47 when you absolutely have to kill every motherfucker in sight."

Jackson's personification of black urban cool is a thing of beauty in itself, and as such merits inclusion in our pantheon of the shamelessly chic.

8. CARY GRANT

Perhaps the most elegant man who ever lived, Cary Grant was a masterpiece of polished taste and refinement. Impeccably dressed, impossibly handome, and irresistably charming, Grant was an icon of style. His performances in the great Hitchcock films like Notorious, To Catch a Thief, and North by Northwest set a new standard for cool detachment and and an ironic brand of grace under pressure.



His extraordinarily suave and seamless comic touch also helped adore him to legions of both men and women. Actively bisexual in his youth, but resolutely heterosexual in his forties and beyond, Grant was also notorious for his vanity, and could rarely be seen in public with a hair out of place or wearing anything but the most impeccably tailored suits and jackets. Cary Grant will always live on in our memories as the coolest exponent of sophisticated style.

9. JACK NICHOLSON

No compendium of cool would be complete without Jack Nicholson, the supreme Hollywood iconoclast who has long revelled in the pleasures of the flesh and railed against political correctness.  Jack has never backed off his highly developed philosophy of sensual abandon, and ranks as the supreme leader of Hollywood's authentic legion of rebels, dedicated to fun and games without guilt or hesitation.  If someone dangerously cuts him off in traffic, Jack will get out of his car, grab a golf club out of the trunk, and smash his transgressor's windshield and headlights.


Jack doesn't believe in coddling the arrogant, and similarly has not patience for the drive to turn men into whimpering slaves to their inner child. "It's absurd the way women try to castrate men by turning us into something we're not meant to be....There are profound differences with the way men’s and women’s brains are wired and the things that make us tick. Women have become too engrossed in their own sensitivity to the point where they've forgotten that men respond to a different set of stimuli.”

“I'm not about to hand over my dick and accept the fact that it’s becoming undignified to have fun. Men like to fuck, and women shouldn't bother to change fifty thousand years of conditioning." Long live Jack!

10. JOHN F. KENNEDY

JFK ushered in a new generation of sophisticated urban cool. His patrician upbringing endowed with him an incalculably sexy way of being. JFK wore the right suits, sunglasses, and button-down shirts long before fashion designers understood the art of dressing men.

He was so far ahead of his time in creating an aura of ironic charm, that it would be hard to imagine any movie star evoking a similar level of laid-back grace and elegance.

Though he was worth several hundred million dollars, JFK was so cool that he rarely if ever carried more than $10 in his pockets, believing it was undignified for a multi-millionaire to actually handle money. His equally pedigreed wife Jackie helped turn the Kennedy White House into a bastion of contemporary style, and the Kennedy presidency came to be known as “Camelot,” so magical and mythical was its hold on the public imagination.

Meanwhile, despite a bad back that dated to his PT boat heroics during WWII and the effects of Addison’s disease, JFK was a major league stud. He helped himself to a rich assortment of beautiful mistresses that included Marilyn Monroe and Grace Kelly and shared more than a few women that other fabled cocksman, Frank Sinatra. 


The Kennedy cool was so impossibly unattainable that subsequent generations have failed miserably in trying to live up to JFK's ardently sly passion for life.

11.  YVES MONTAND

This French icon was actually born in Italy with the given name of Ivo Livi before moving to France as a child and growing up in Marseille. Working his way to fame by singing and dancing in music halls, Yves Montand was Europe's answer to Frank Sinatra.  An accomplished actor and singer, Montand cultivated a large following with his world-weary manner and abundant Gallic charm and had affairs with a multitude of gorgeous actresses including Ingrid Bergman, Monica Vitti, and Marilyn Monroe, to name but a few.

Montand was such a charming rogue that women still adored him even after he had abandoned them for the next conquest! Montand stood tallest among the many great French screen stars of his day, and radiated an astonishing combination of urgency, complexity, humility and quiet authority in films like  Costa-Gavras' Z, The Confession, as well as in Grand Prix, La Guerre est finie,  and Vincent, Francois, Paul, and the Others. What was perhaps most astonishing about Montand was how cool he looked with so little effort.
 




12. GEORGE CLOONEY

A master of cool elegance, George Clooney is a throwback to the days of Spencer Tracy and Humphrey Bogart, an era when men were proud to love hard and live to excess. Clooney's square-jawed handsomeness has enabled him to convert his abundantly infectious manner to full advantage.

As a classic leading man, no one other than Clooney can legitimately claim the mantle once reserved for Harrison Ford and Robert Redford.  Clooney is also one of the great rogues of modern Hollywood, taking up where Warren Beatty and Jack Nicholson left off in their glory days. George is a consummate gentleman, however, and though his workaholic ways often cause his women to jump ship. Clooney remains the classic Everyman actor of his time.  His biggest box-office success to date Ocean's 11, a remake of the Frank Sinatra Rat Pack classic, merely reinforces his stature as the current king of Hollywood cool.

His purchase of a magnificent villa along Italy’s Lake Como has given him an added veneer of innocuous desuetude.  Not only has Clooney endeared himself to the local population, but his villa has enabled him to find peace of mind away from the constant media attention.  Instead of bedding every starlet imaginable, Clooney has preferred to devote himself to his work.  Despite flops like “Solaris” and “Confessions of a Dangerous Mind,” Clooney has carved out a modest success as producer, director, and actor, resulting in ambitious films such as “Syriana,” “Good Night and Good Luck,” and “The Good German.”  His work in “Michael Clayton” (2007)confirmed his formidable acting skills.

13.  MUHAMMAD ALI

The sporting world may never see another boxer with as much self-styled arrogance, nerve, and balletic elegance as Muhammad Ali. The sensual slugger danced his way around the ring with a matchless capacity to inflict laser-sharp and lightning fast jabs which
would slice open an opponent's face.

The subject of the new Ridley Scott-Will Smith biopic, Ali was a true historical and cultural phenomenon, a man who was a legend in his own time to the point where his ringside artistry turned him into a mythological figure.

Ali was also a brilliant self-promoter, fond of ringside poetry that was encapsulized in his boxing credo: "Float like a butterfly, sting like a bee." Not merely "the Greatest of all time," as he proclaimed his mastery, but also one of the coolest.

14.  JIM MORRISON

The lead singer for The Doors was a revolutionary poet in his own right, an implacable psycho-sexual troubador whose music expressed a profound rejection of conservative values.  Morrison waged an hallucinatory crusade against the demons in the human soul, and cast a sensual shadow over the sixties' social, political, and cultural upheavals. An admirer of William Blake, Morrison's haunting lyrics amounted to nothing less than a passionate venting of
deep-seated psychic fury against an indifferent universe. Morrison enjoyed pricking the sensibility of the conversative establishment, and was famously arrested for  exposing himself onstage.

There are many pretenders to the throne of musical rebellion, but Morrison was an authentic ambassador of a sexually-charged revolt against complacency and repression. On the back of fellow Doors  musician Ray Manzarak's throbbing keyboards, Morrison was a cunning sexual icon whose vocal tracks steered music into territory that no band has ever truly been able of rediscovering.  When held in relief against flatulent pop bands such as Coldplay, it is very clear that Jim Morrison was infinitely cooler.

15. KEITH RICHARDS

Keith Richards is the rock world's most famous substance abuser. He was a heroin addict for nearly twenty years. He would play entire world tours in which his supplies of smack and cocaine were laid out
in lines on top of his amplifier for easy mid-show sampling. It has become a cliche for other rock stars of his vintage to renounce their narcotic past and swear allegiance to new healthy lifestyles. But Richards has never apologised.

He still smokes like a chimney, drinks like a fish and one can safely assume that when he visits his house in Jamaica, where some of his closest friends are Rastafarians, he doesn't just go for the sunshine. Forget the quality of his playing: his survival is miracle enough.  He was a rebel and an outlaw. Rock magazines told their wide-eyed readers wild tales of how he carried a gun with him at all times. He was said to stay up for at least three days at a time: nine was his record. Photographers invariably shot him looking lean and mean behind a veil of smoke, a Marlboro clasped between fingers on which sat his skull-and-crossbones ring.


According to New Musical Express, Keith Richards is "The world's most elegantly wasted human being." And about Mick Jagger, his Rolling Stones co-writer and arch rival, Richards once declared: "Mick could be very prissy." If Mick was what made the Stones sexy and outrageous, Keith was what made them bad, and....very cool.


16.  PORFIRIO RUBIROSA

This stylish Argentine rogue of Italian descent ranks as the ultimate playboy as gigolo of the last century. The son of an Argentine army officer, Rubirosa was an outstanding international class polo player as well as one of Europe's most mesmerising and celebrated jet setters of the forties and fifties.

Married for a time to Barbar Hutton, the heir to a fortune of several hundred million dollars, Rubirosa was fabled not merely for his abundant charm, but also for a penis that has variously been described as horse-like and salami-shaped.  In her memoirs, Hutton wrote that Rubirosa was “grotesquely proportioned.”

Not only was the length and thickness of his appendage of staggering proportions, but his testicles apparently were so large that he never wore underwear, finding them too painful and constricting! So legendary was his dick that celebrities in Hollywood would ask for the "Rubirosa" in restaurants as a synonym for the foot-long sized peppermill!





On one occasion, Rubirosa's personal valet accidently burst in on him during a love-making session, and the enraged stud leapt up off the bed and slammed the door shut, but in the meantime giving the valet a glimpse of his famous appendage.

Fittingly, Rubirosa spent his time seducing various European heiresses and aristocrats before dying in a car crash when he wrapped his Ferrari around a tree, about as "cool" a death as anyone can ever hope for.

17.    BRYAN FERRY

The one-time Roxy Music lead singer who became instantly identifiable for wearing white dinner jackets and tuxedos, Bryan Ferry has made a career out of suave sophistication and a dreamily romantic musical repertoire. Songs like "The In Crowd", "Avalon," "Kiss and Tell," - all helped turn Ferry into the thinking woman's sex symbol. His bedroom eyes and scattered shock of black hair swerving over his forehead endowed him with a certain veneer of decadent aristocracy.

Always known for being a master of style, Ferry was one of the most oft-photographed celebrities of the seventies and eighties, appearing on the covers of magazines ranging from Interview to Rolling Stone to Vogue.  The son of a coal miner, Ferry cast such a casually bemused presence on stage and off that he evolved into a cosmopolite icon revered as much for his music as for his mannered legato.


18. MILES DAVIS

A legend at the age of 21, Miles Davis was a true musical genius who is credited with having given birth to the era of "cool jazz."  Blessed with fine features and an almost irridescent skin tone, Davis was as handsome as he was talented, a man who was the jazz world's king of sex as well as its most influential arranger. 

He began his career in his late teens touring with the legendary Charlie Parker, and would eventually collaborate with virtually all of jazz's greatest artists including Coleman Hawkins, John Coltrane, Thelonius Monk, Bill Evans, Sonny Rollins, and Herbie Hancock.

The Davis opus includes seminal albums like Birth of the Cool, Miles Ahead, Sketches of Spain, and the utterly revolutionary Kind of Blue, hailed by virtually every music critic as the finest expression of modern jazz.  In his personal life, Davis was a chronic heroin abuser for much of his life and notorious for his brusque manner and cutting wit. 

On one occasion shortly before their final split, the great saxophone virtuoso John Coltrane soared off into an overly long and impossibly fast solo, and then apologized for "not knowing how to stop." Hardly impressed with Coltrane's mea culpa, Davis dryly replied: "Try takin' the motherfucker out of yo' mouth."






19.  DAVID BOWIE

From Ziggy Stardust to the Thin White Duke, David Bowie is famous for creating a body of music that is deeply intertwined with a corresponding style and sensibility. Bowie has been able to successfully reinvent himself several times over while still retaining a distinct and relevant musical identity.  Having studied mime and interior design at university, Bowie consistently framed his music with a look that ranged from glam-rock to lounge lizard to his hard-rock incarnation with the experimental group Tin Machine and guitar wizard Adrian DeLeuw.  Songs like Heroes, Gene Genie, Let's Dance, Ziggy Stardust, Aladdinsane, Blue Jean, Space Oddity, Fashion, Young American, Ashes to Ashes, et al. have all become part of our cultural landscape and defined David Bowie as a supreme arbiter of musical cool.

20.  STEVE McQUEEN

It's hard to imagine Steve McQueen in any setting in which he wouldn't be cool. Certainly his film work was one continuous display of massively understated self-confidence and sly ambition. Take, for example, McQueen's laid-back detective in “Bullit”, in which he drove his Mustang 440 in one of the film world's all-time great car chases. We also remember McQueen as Hicks, the unflappable Yankee POW whose motorcycle acrobatics provided a stirring finale to “The Great Escape”. And in Sam Peckinpah's “The Getaway”, McQueen was a master of laconic sexual conceit opposite Ali McGraw (during the making of that film McQueen actually seduced McGraw away from her then-husband Robert Evans) and coolly blew away the gang bent on hunting them down. 

Throw in films like LE MANS and THE THOMAS CROWN AFFAIR (which was the ultimately "cool" film of the seventies), and it's easy to
appreciate the icy ardor of the McQueen persona. In addition to his filmed roles as a fast driver, McQueen was an avid car collector who had several Porshes specially designed for him.  Also a contender for the ranks of the greats as one of those guys who look impossibly superb in shades.  One of the best photographs of McQueen was taken by Robert Claxton while McQueen was driving his Porsche with one hand on the wheel and posing for the camera.







21.  JEAN RENO

From Enzo in THE BIG BLUE, to Bob, Le Nettoyeur in
NIKITA to Leon in THE PROFESSIONAL, Jean Reno (he is
actually Spanish and his real name is Don Juan Moreno
Errere y Rimenes) has established a roguish screen
presence as a man of few words but clear purpose. His
gravelly baritone is merely one of a number of
trademark characteristics which convey a no-nonsense
approach to taking care of business. He is omeone whom you
would surely not want to come up against in a dark
alley.



Though Reno is one of France's reigning screen
stars (LES VISITEURS was one of his greatest hits
outside of his Luc Besson films), he has also forged
an international career appearing in films like
GODZILLA and MISSION: IMPOSSIBLE. Away from a film
set, Reno is a hard-drinking, hard-living Parisian who
always has time for his fans and whose personality
strongly resembles that of Vincent, the honorable
Frenchman from RONIN.

"I like to play characters like Vincent or Leon," said
Reno. "They're tough, but they have a soul.  I
wouldn't like to play Le Nettoyeur again, he's too
much of an ice-cold killer, plus he's dead!"

22.  DENNIS HOPPER

After breaking into Hollywood alongside James Dean in
REBEL WITHOUT A CAUSE and GIANT, Dennis Hopper created
a cult following for himself when he directed and
co-starred in the definitive 60's film, EASY RIDER. He
was one of the leading figures of the American
counter-culture, and, unknown to most people, an avid
collector of American pop art. He was also a legendary
drug and alcohol abuser, reaching his psychotropic
nadir in 1983 while shooting a film in Mexico.

"The police found me running naked in the town square and
the studio had me sent back to L.A. and had me checked
into the mental ward at Cedar’s Sinai hospital.  I was
a total zombie, mumbling and talking nonsense.  The
doctors would wheel me out, show me to the interns and
point to me and say, ‘This is what happens when you do
too many drugs."
Hopper would susequently give up drugs and booze, and
make a vigorous comeback as both a director (THE HOT
SPOT, COLOURS) and Hollywood villain, immortalizing
himself as David Lynch's amyl nitrate sniffing
lunatic, Frank Booth, in BLUE VELVET.

In addition to brilliant villainous riffs in RED ROCK WEST, SPEED, and WATERWORLD,  Hopper is a cult figure amongst European cinephiles for his turn as Tom Ripley in Wim Wenders' THE AMERICAN FRIEND.  Looking back at his career, Hopper will always be remembered for his immortal line, delivered to Isabella Rosselini's character in BLUE VELVET:  "Daddy wants to fuck!" Very cool indeed.

23.    CLINT EASTWOOD

One of the cinema's few remaining heroes, Clint
Eastwood has carved out a screen persona as a man of
noble aspiration and cold efficiency. First, as the
tight-lipped "man with no name" in Sergio Leone
classics like THE GOOD, THE BAD, AND THE UGLY,
Eastwood established himself as a lone crusader amid
the anarchic forces of the Wild West. 


Then, as Dirty Harry, Eastwood subverted the icy
iconoclasm of the western gunslinger into the cool
aesthetic of the modern day avenger seeking to restore
balance to the war between good and evil. Ever since,
Eastwood has cast an aura over his films that invites
us to consider the solitude of the human spirit. 

Directing and starring in films like PLAY MISTY FOR
ME, THE EIGER SANCTION, and THE UNFORGIVEN, Clint
Eastwood has evoked the struggle of the individual who
comes to terms with an irrational universe. His
chiseled features, long gait, and menacing gaze have
rightfully established Eastwood as a man of mythic
proportion. But what does Eastwood himself say about
his formidable reputation as Dirty Harry, the role for
which he'll be best remembered? "Well, I'm a little
less belligerent. I don't go around asking people to
"make my day."






24. PAUL NEWMAN

How could we avoid including the man who starred in
COOL HAND LUKE? Paul Newman has been emblematic of a
fiercely independent attitude and refusal to play the
game by the rules.  Roles in CAT ON A HOT TIN ROOF,
THE HUSTLER, and HUD served to capture the pent-up
volatility to Newman's person, while his work in
HARPER, BUTCH CASSIDY AND THE SUNDANCE KID, and THE
STING captured a charismatic grace under pressure that
forever enshrined Newman as one of the most engaging
yet enigmatic actors of his era.  It may be difficult
to articulate the moody and emotionally distanced
hubris that Newman seemed to evoke, but certainly much
of his brilliance lay in the studied cool and
contained anger he brought to his screen portrayals.

Outside his films, Newman the man is justifiably proud
of his work in funding charities through his Newman’s
Own Salad Dressing and his campaigning for various
civil right’s and ecological causes. A long-time
supporter of the Democratic Party in the United
States, Newman was a vociferous supporter of the
anti-Vietnam War movement, and has long spoken out in
favor of nuclear disarmament.


To his further credit, Newman desperately resisted his
celebrity, hating all the attention that was focussed
on his handsome features and piercing blue eyes.
"People would come up to me and say, ‘Let us see your
beautiful blue eyes,’ And you just want to...I
dunno...punch them. I’ve always hated being thought of
as a pretty boy because that means no one is looking
at your performance. You kill yourself to create a
character, and you feel that no one is thinking about
that"



25.  JOHN TRAVOLTA

As Tony Maneri in the 1977 disco era hit, SATURDAY
NIGHT FEVER, John Travolta was the coolest man alive.
But ten years later, his career was in free fall and
Travolta was a has-been. Then came PULP FICTION, and
with it Travolta was resurrected in the role of
Vincent Vega, the heroin-addicted hitman assigned to
look after a mobster's kinky girlfriend.  Perhaps the
ultimate cool moment in the film came when Travolta
was dancing the twist with Uma Thurman, a scene that
achieved a rare poignancy by casting an ironic glance
at Travolta's former disco persona. Travolta’s sly,
sweet, and offbeat performance was nothing short of a
revelation for a man whom everyone believed had been
permanently relegated to the nostalgia heap.

Ironically, Travolta always resisted buying into the
hype that followed him after Saturday Night Fever. He
tells the following anecdote to explain the dangers of
drowning in one's cool. "Every time I've ever let
myself think I'm cool, I've got into trouble. One day
I decided to take this red '64 Jaguar I own out for a
drive. I drive it maybe twice a year for fun. I was
late for a meeting with a director and I took a look
at the Jag and I thought to myself, ‘You know what, I
bet if I were to put the top down, smoke a cigar, and
play the ‘shabadabada’ music from A Man and a Woman,
I’d start feeling a whole lot better.’  So I drive
down Sunset Boulevard, I have my sunglasses on and
everybody is staring at me and I’m thinking to myself,
‘hey, I’m just soooo cool!’"

"Boom! The car conks out right at this curve that no
one ever wants to have their car break down at because
it’s dangerous.  So I panic, my face gets red, people
are honking and swearing at men, yelling ‘Fuck you...
Fuck you...’, and giving me the finger. My face is getting redder and redder as everyone is screaming at me."


"Then when I get out of my car people recognize me and
then they’re like, ‘Oh, can we help you?’ And I”m
like, ‘No, I’m fine!’ And I wasn’t fine! Then suddenly
this guy from one of the big mansions comes out and
helps me push my car into his driveway so I wasn’t
blocking traffic any more.  That’s what happens to me
every time I ever actually believe, even for one
second, that I’m cool."

26. JEFF BRIDGES

Although one might not ordinarily think of Jeff
Bridges as a particularly cool figure, his hilarious
performance in the Coen brothers' THE BIG LEBOWSKI
earns him a special place in our pantheon.  Playing
"the Dude," a long-haired, spaced-out slacker
seriously lacking in ambition and any observable life
skills, Bridges delivers an inspired performance that
reeks of laid-back cool. Sporting an outrageous
Hawaiian print shirt to match his stoner personality,
The Dude (a term of dubious validity bestowed him by
his equally off-beat and dim buddies [Steve Buscemi
and John Goodman]) brings a wealth of philosophical
shallowness and self-satisfied sloth to his world of
urban fringe-dwellers cum bowling buddies. If one
recalls some of Bridges' previous films - JAGGED EDGE,
SUSIE AND THE BAKER BOYS, THE FISHER KING - there is a
remarkable air of sophistication and elegance to his
work. But as The Dude, Bridges turns that bearing and
poise on its head and in the process creates an
amiably ineffectual and highly stylish loser.



27. TIGER WOODS

With his 14th major championship now in the bag,
Tiger Woods has set a standard for sporting excellence
that may well never be match.  The way he won the recent U.S. Open Golf championship with one pressure-packed long putt after another was other-wordly.  His ability to play his best under the gun is the very definition of being
cool under pressure.  Arnold Palmer, a great golfer of
the past, has this to say about Woods :  « Tiger has ice running through his veins – no one has ever had his
ability to produce his best golf when everything is riding on one shot. »

28. DEAN MARTIN

The man who seemed to have a cocktail glass
permanently attached to his hand, Dean Martin was a
classic figure of world-weary, laissez-faire cool.
With songs like Everybody Loves Somebody and
performances in films like Ocean's 11, Airport, and
Five Card Stud, Martin cut a sleek and sexy persona
for himself.

His leasurely and affable manner was a contrast to
fellow Rat Pack member Frank Sinatra's more
combustible image, yet Martin was in his own way able
to define himself as tuxedoed lounge lizard. Though
Martin was always identified as an amiably drunken
figure on his TV series, he never lost his cool nor
his sense of playful charm.










29.  SERGE GAINSBOURG

For a time, Serge Gainsbourg was the ultimate
definition of roguish French cool.  Unshaven, unkempt,
and definitely unorthodox, Gainsbourg affected the
kind of hyper-cool persona that had some of France's
most beautiful women craving to enter his domain.  He
was married to Jane Birkin for fifteen years, and
their daughter, Charlotte Gainsbourg, is one of
France's leading actreses today. Serge gave us a
series of celebrated "cool" songs which were sung in a
kind of desultory, raspy, semi-spoken monologue, and
often in tandem with Birkin.
 
Often featured on French talk-shows with a cigarette
hanging from his mouth and heavily intoxicated,
Gainsbourg created a scandal when he burned a 500
Franc note on national TV.  He also caused controversy
when he told supermodel Naomi Campbell that she had a
mouth which would be "great for blow-jobs."

30.  ANDY WARHOL

The self-styled leader of the American pop art
movement, Warhol pioneered the idea of turning his
Campbell Soup Cans, Brillo Pads, and celebrity
photo-prints into definite expressions of the American
art scene.  He helped propel the careers of the great
abstract expressionists like Robert Rauschenberg and
Jasper Johns, while also serving to legitimize other
pop art icons like Roy Lichtenstein, Jim Dine, Eduoard
Rocha, and perhaps most notably, Jean-Michel Basquiat.
Warhol created a cult of personality around him and
his high-society, Studio 54 entourage, and created a
forum for American pop culture with the founding of
INTERVIEW magazine. He defined the post-modern concept
of cool with the phrase: "Everybody will be famous for
fifteen minutes."


31.    JAMES HUNT

The former Formula 1 world driving champion, James
Hunt was the last man who truly represented the
hard-drinking, hard-living, hard-loving spirit of the
race car driver. With his blonde locks and tall, lean
frame, Hunt was the classic playboy of the Formula 1
circuit in the seventies.  He would show up at
post-race press conferences in bare feet and Hawaiian
flower-print shirts, and was a far cry from today's
robotized drivers like Michael Schumacher and his lot.
Hunt loved to party throughout the race season, and
was often photographed with a different girl or girls
coming out of his hotel room from one race to the
other. When he got bored with racing, Hunt turned his
attention to the BBC commentary booth where he
distinguished himself as a sharp-tongued criti,
describing Formula 1 driver Andrea de Cesaris as a
"lead-footed truck driver" and Alain Prost as "the
only Formula 1 champion who wants to win as slowly as
possible."

Hunt died of a heart attack at the premature age of
45, yet he packed more living into his years on earth
than most people can dream of.


32.  GIANNI AGNELLI

No list of world class cool guys could possibly omit
the late Gianni Agnelli, the legendary Fiat Chairman,
and Italian billionaire who wined and dined women for
over fifty years.  Whether aboard one of his yachts or
inside his glittering marble palazzos, Gianni Agnelli,
otherwise known as "L'avocatto", was the model for the
typical Italian jet-setting playboy, fond of skiing,
swimming, sex, and power. 




He was so cool that his personal habit of wearing his watch over his shirt cuff became adopted by men all over the world. Agnelli was also a master fashion stylist, who often
looked like he stepped out of a magazine.  Very, very
cool.

33.  ERROL FLYNN

There has probably never been a man of such irrepressible sexual appetites as Errol Flynn. Not only was he an insatiable lover, but he made it almost his life's work to seduce, charm, and exhort women to his bed at virtually every opportunity.  The phrase "In like Flynn" evolved out of his reputation as Hollywood's most sexually brazen playboy, a man who nearly ruined his career when he was charged with statutory rape for having taken two 14-year-old girls on his private yacht to his sexual haven in Port Antonio, Jamaica. 

Blessed with a prodigious member, Flynn was said to have had sex with virutally every leading actress of his time, as well as secretaries, school girls, and hotel maids.  Wherever the female flesh was to be found, Errol was like a shark in pursuit of orgasmic ecstacy.  Flynn famously turned seduction into a game where he set the rules and made women his sole ambition.

In film roles like Captain Blood, The Adventures of Robin Hood, and Gentleman Jim, Flynn captivated the public imagination with his dashing features and effortless grace.  Flynn was certainly one of the coolest men of his day, and his rakish elegance serves as a lesson to all those who would follow in his cool footsteps.