The 25 Coolest Sportsmen Of All Time

What, no Beckham?

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For Esquire's special July 2016 sports issue, we've rounded up the 25 coolest men ever to pick up a bat, kick a ball or race a car.

There are the men who not only changed their sports but influenced the way we dressed and how we think of athletes.

Icons all, and no - not one of them is David Beckham (sorry, Becks).

Björn Borg

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Everyone who saw it remembers the tie-break. John McEnroe prevailed 18–16 after nearly 25 almost-excruciating minutes to take the 1980 Wimbledon final into a fifth set. But the truly remarkable thing happened next. "And then there follows a moment which must rank among the greatest in sport," Tim Adams wrote in On Being John McEnroe. "It is the moment when Borg walks out to serve once more, two sets all, one set to play, as if nothing had happened."

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Borg once told McEnroe, "I'm two people" and that's true. There was the iceman that Ilie Nastase called "The Martian" because he never flickered whether he won or lost. But the essential attraction — besides his impeccable pinstripe Fila uniform and kangaroo-skin shoes — was the other Borg that remained unpredictable. It was this Borg who, after losing to McEnroe at the 1981 US Open, simply and without drama left the court and went straight to the airport in his tennis gear. He retired soon after.


It's a mark of Pelé's excellence that, despite scoring 1,283 goals, it's three efforts that missed that pop into our heads when we think of him: the one from the halfway line against Czechoslovakia; the dummy versus Uruguay; and when Gordon Banks clawed his header over the bar, all from the 1970 World Cup. Pelé was so complete, so flawless, that it was when he fractionally erred we could best appreciate him.

The revisionist view of Pelé has been building in recent years. Garrincha, the flamboyant winger, is more loved in Brazil. Pelé was fortunate that the greatest of his three World Cup wins came in 1970, with the world tuning in for the first time in colour. Yet, as he himself said, such protests miss the point: "In music there is Beethoven and the rest. In football, there is Pelé and the rest."

Eddy Merckx

He was called "The Cannibal", he's indisputably the most dominant cyclist of all time, and this is why, in numbers:

Races, out of around 1,800 entered, that the Belgian won in his career (1965–'78). At his most dominant, in 1971, he won 45 per cent of the events he started.

Tours de France won. Plus five editions of the Giro d'Italia and one Vuelta a España.

Minutes Merckx was unconscious after a 1969 crash. He suffered a displaced pelvis, head and spinal injuries. Afterwards, he was in constant pain on the bike, shuffling in his saddle interminably to get comfortable.

Kilometres Merckx rode solo across the Pyrenees on Stage 17 of the 1969 Tour de France. He was leading comfortably, but wanted to destroy the field. "That Belgian guy, he doesn't even leave you the crumbs," said the daughter of a rival French rider, before anointing him with a nickname that would stick. "He's a real cannibal."

Jean-Claude Killy

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When Hunter S Thompson, assigned by Playboy, met Killy in the late Sixties, the skier called to mind Jay Gatsby: he had, in F Scott Fitzgerald's words, "one of those rare smiles with a quality of eternal reassurance in it." Or, as Thompson put it: a smile that "combines James Dean, Porfirio Rubirosa and a teenage bank clerk with a foolproof embezzlement scheme." Killy was fresh from unprecedented success at the 1968 Winter Olympics, winning all three alpine events. He immediately retired — what else could he achieve? — and moved into the then-new arena of mega-bucks endorsements.

For Thompson, it was an uncomfortable transition. For Killy, it was the way sport was going, and he's essentially, perhaps sadly, been proved right. "I am tired. Tired!" he exploded at Thompson. "Two weeks from now I can go home to rest and spend all my money."

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Eric Cantona

Let's clear this up: Cantona deeply regrets the events of 25 January, 1995, when he jumped into the crowd at Selhurst Park to assault a Crystal Palace fan. "I didn't punch him strong enough," he told FourFourTwo in 2008. Long before he started appearing in films, Cantona already considered himself "an actor". Ask him why he played with collar up, he'll offer a Gallic shrug — no man, not even Depardieu, is more French than Cantona — and declare simply that it was cold one day. The team won; he kept doing it. Fans might take football seriously but to Cantona it was just a game. "The more you see," he said, "the more you realise that life is a circus." We never saw him decline: Cantona retired, aged 30, after winning five league titles in six years. Sir Alex Ferguson said he had only four "world-class" players at Manchester United — Cantona, Giggs, Scholes and Ronaldo. Have that, Keane and Beckham.

Arnold Palmer

Palmer, now 86, would deserve a place on this list for his Munsingwear polo shirts, flat-fronted slacks and slung-on cardigans. He strode the fairways on the way to seven major titles, hair slicked, cigarette falling off his lips, like Don Draper's playing partner. But the real legacy of golf's king of cool is that he didn't endorse a sports drink, he created one, when he came home from a round one day and doctored his wife's iced tea with fresh lemonade. "Before he knew it, he was overcome with the sensation: 'I've just created the world's most refreshing drink… registered trademark,'" said the comedian Will Arnett in an ESPN short documentary, The Arnold Palmer. There's disagreement on the perfect mix, so let's hear it from the Arnold Palmer himself. "Oh iced tea has the dominant side," he says, suggesting a ratio of around 3:1. "If it doesn't, it isn't really right."

Ayrton Senna

When it rained, Senna reigned. Nowhere was this more evident than at England's Donington Park in the 1993 European Grand Prix. In dank, biblical conditions, he started the race fourth on the grid in his underpowered McLaren, and had dropped back to fifth by the first corner.  In front of him were Michael Schumacher, Karl Wendlinger, Damon Hill and Alain Prost — his great nemesis — men who would go on to win 12 world titles. But in the space of one circuit (little more than two minutes), Senna shimmied past each of them. By the end of lap two he was four seconds clear; at the end, only Hill wasn't lapped at least once. It was one of F1's most nerveless performances — maybe even the sport's finest lap — but in just over a year Senna would be dead, aged 34. "It was a race that will live in my memory forever," said Murray Walker.

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Lester Piggott

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Yep, you read that right: Lester Piggott, the mumbling, gaunt jockey and one-time tax-dodging jailbird. He had a reputation as a cantankerous bugger, but that might just have been because he was permanently starved. At 5ft 8in — tall for a jockey, hence his nickname "The Longfellow" — he spent his career about 30lbs under his natural weight. Breakfast, famously, was a cigar and a cough; a Yorkie bar was kept under lock and key and eaten one square at a time for a sugar kick. "A face like a well-kept grave," was one memorable put-down. 

But Piggott always had a dapper style and a knack for the dramatic that led to comparisons with Muhammad Ali. Never more so than in 1990, when he returned aged 54, after five years out of the saddle — including a year at Her Majesty's pleasure — with a dramatic sprint on Royal Academy to win the Breeders' Cup in the US, the richest prize of his career.

Muhammad Ali

Where to start with the most influential athlete of the 20th century? Perhaps a self-composed poem written in 1964, on the eve of his first world title fight, as Cassius Clay, against the formidable Sonny Liston:

Clay comes out to meet Liston and Liston starts to retreat

If Liston goes back an inch farther he'll end up in a ringside seat.

Clay swings with a left, Clay swings with a right

Just look at young Cassius carry the fight. 

Liston keeps backing but there's not enough room

It's a matter of time until Clay lowers the boom. 

Then Clay lands with a right, what a beautiful swing

And the punch raised the bear clean out of the ring. 

Liston still rising and the ref wears a frown

For he can't start counting until Sonny comes down. 

Now Liston disappears from view, the crowd is getting frantic

But our radar stations have picked him up somewhere over the Atlantic. 

Who on Earth thought, when they came to the fight

That they would witness the launching of a human satellite?

Hence the crowd did not dream when they laid down money

That they would see a total eclipse of the Sonny!

Fred Perry

Given the reverence with which Perry's name is invoked these days, you'd guess he was pure Establishment. In fact, it was the opposite. His father was a cotton spinner in Stockport and officials at Wimbledon — where he won the title in 1934, '35 and '36 — couldn't stand him, in part because of the self-admitted "gamesmanship" he used in matches. Irked by this disapproval, Perry became a US citizen in his late twenties and served with the US Air Force in World War II. He had four marriages, but was better known for his flings with Marlene Dietrich and Jean Harlow.

Perry didn't invent the polo shirt — that was René "The Crocodile" Lacoste — but he did have a hand in popularising the sweatband. When he started the company that still bears his name, he wanted the logo to be his beloved pipe. Regrettably, he was dissuaded and repurposed Wimbledon's laurel wreath instead.

Viv Richards

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Although no one ever saw him wear it in public, it's said Viv Richards did in fact own a helmet, and even tested it in practice. But he felt slow and complacent wearing it, and the grille made it harder to glare down the pitch at the bowler. Richards was a great batsman but he was a samurai master in intimidation. He took extra pleasure thrashing England — he averaged 63 — because of the imperial legacy in the West Indies.

Despite not wearing a lid, Richards was only once hit on the head. It happened in 1979 when Rodney Hogg bowled a bouncer to him on a dodgy MCG pitch. Richards picked himself up, glowered at Hogg, chewed his gum, and then bludgeoned him for 10 an over for the next six overs. Richards finished with 96; Hogg left the field with a strained back and didn't play Test cricket again for a year.

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Julius Erving

There is a special languid elegance that belongs to a great basketball player; these men — often so gangly and awkward off the court — suddenly make perfect, co-ordinated sense. Julius Winfield Erving II, or Dr J as he should always be called, was especially acrobatic even, at times, balletic. Although just 6ft 7in, Dr J's signature move was the dunk, a manoeuvre he revolutionised in the Seventies with the New York Nets and Philadelphia 76ers and turned into an art form. Two of his dunks stand out and can only truly be appreciated in slo-mo: one, against the LA Lakers in 1983, is the "rock the baby", where he rolls the ball back and forth before dispatching it like a windmill. Our favourite, though, is from the 1977 NBA finals against the Portland Trail Blazers where Dr J slaloms past five defenders before soaring from beyond the free-throw line. Basketball would never be the same again.


An intellectual, a philosopher, a smoker, a drinker, a revolutionary and a proper medical doctor. Sócrates is probably the only footballer in history of whom it could be said that what he did off the pitch was as interesting as what he did on it. His heroes were Che Guevara and John Lennon, his casual reading was Thomas Hobbes and Machiavelli (whom he preferred to his namesake) and he campaigned passionately for democracy to oust the US-backed military dictatorship that ruled Brazil for much of his life. Instead of a sponsor's logo, his Corinthians team had "Democracia" emblazoned on their shirts. On the field, Sócrates was the brains (and captain) of the great underachieving team that were out-muscled by Italy in the 1982 World Cup. He had even given up drink and cigarettes in preparation for the tournament; when Brazil lost on 5 July it was for him no less than "the day football died".

Gareth Edwards

"If the greatest writer of the written word would have written that story," said Cliff Morgan, the wonderful commentator, "no one would have believed it." Sometimes we are unaware of history as we are watching it, but when the Welsh scrum-half Gareth Edwards bolted from out of frame to score for the Barbarians against New Zealand in 1973, it seemed unlikely even then that the sport would see such fluid perfection again. 

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In those days, rugby was a game of sidesteps and sideburns, and no man is more evocative of the era than the 5ft 10in Edwards, who weighed about the same as one of Sonny Bill Williams' arms. Even back then, he was usually the smallest man on the field, but he made up for it with his athleticism and canny reading of the game. Will Carling has said Edwards alone defies generational changes in the sport: "He is the one guy I can say that would have been great whenever he played."

James Hunt

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The 1976 Formula One World Champion had a style that was anti-style: no rules, no boundaries, no regrets. He lived a short, eventful life:

Age 10: Starts smoking and never gives up.

Age 26: His Formula One career begins with the Hesketh team. He wears a patch on his overalls that reads, "Sex: Breakfast of Champions." 

Age 29: Wins the World Championship. In the two weeks before the decisive race in Japan, it's speculated that he sleeps with 33 BA stewardesses.

Age 32: Retires, becomes a budgerigar breeder and commentator. Asks the BBC not to broadcast his commentaries in apartheid-ruled South Africa; but when it does so, he gifts some of his fees to anti-apartheid activists.

Age 35: Turns up late for his second wedding. His brother has to buy a tie for Hunt on the way to the ceremony.

Age 45: Dies of a heart attack.

SEE ALSO: TAG Heuer release limited edition Formula 1 James Hunt watch

Ray Robinson

Robinson was a natural-born showman. Outside the ring, he owned a flamingo-pink Cadillac convertible and a nightclub in Harlem called Sugar Ray's; he went on the road with a valet, barber/golf pro, masseur, voice coach and dwarf mascot. Despite fighting 200 times, he was broke almost the minute that his boxing career ended. "I went through four million dollars," he admitted, "but I have no regrets."

He may have been flashy but there was steel, too. Robinson was never knocked out in over a quarter of a century. He faced Jake LaMotta, The Raging Bull, six times, winning five. Before the pair's last encounter in February 1951, Robinson drank a glass of cold, fresh cow's blood, sprinkled with salt and pepper, when the fighters met to sign contracts. Even LaMotta looked horrified. "All right," said Robinson. "When I'm still dancing in the last round and you're dragging, you'll know why."

Alex Higgins

Have you got a spare six minutes, 17 seconds? Sure you have. Go on YouTube and hunt down Alex Higgins' break of 69 against Jimmy White in the semi-final of the 1982 Snooker World Championship. Higgins is known for his many outrageous acts: sword-fighting with Oliver Reed; pissing in the dressing-room sink while booked on the BBC's Pot Black; throwing his cue like a spear at an annoying spectator. But before — and remarkably during — all that, he was a courageous, dazzling snooker player. 

When Higgins came to the table in that semi-final, he was 59–0 behind, a frame from defeat and — to be frank — steaming. He had been drinking all match and White admitted later he'd been waiting for it to kick in. But Higgins, playing with a dummy in his top pocket, a reminder of a promise he made to his 18-month-old daughter, somehow wins the frame, the match and later, tearfully, the tournament.

Bobby Moore

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Recalling Moore's fastidious performances on the football pitch, it's no surprise he had some obsessive-compulsive tendencies off it. From youth, he hung his clothes light to dark: "It was almost an aesthetic pleasure to open the wardrobe," his first wife Tina said. He developed a technique for drying himself in the bath that ensured not a drop of water fell on the floor and it's said he ironed bank notes. On the field he disliked heading the ball because he considered it messy.

There was considerable chaos in Moore's life, too: he was an alcoholic (though only ever drank halves in public) and he died, aged 51, broke and a columnist for the Sunday Sport. But he will always be remembered for his elegance and unruffled deportment: that Lego side-parting and pristine kit. As Michael Caine said, "You'd have given him the job of England captain without seeing him kick a ball."

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Jim Clark

When Clark was killed racing at Hockenheim in 1968, his Lotus-Cosworth flying off into woodland, no one knew for sure what went wrong. The conditions were abysmal, but that never seemed to rattle the Scot; at the 1963 Belgian Grand Prix at Spa, he started eighth, but after 17 laps he'd lapped almost the entire field. It could have been driver error, but none of his fellow competitors believed he was capable of making a routine mistake. Aged 32, he had won two World Championships (and an Indianapolis 500) and won 25 Grands Prix, more than any other driver. Investigators eventually pointed to a deflated rear tyre. Many will say Clark was the greatest F1 driver of all time, but more unusual — in this most ego-fuelled of sports — is that no one has a remotely snarky word to say about him as a man.

Imran Khan

In the Seventies and Eighties, Imran Khan was a regular at Tramp nightclub and owned a luxurious flat off the King's Road in Chelsea, which had a golden canopy over the bed and a depiction of tigers on the frame. He was well-known as a shagger; the novelist Hanif Kureishi has noted that some young Pakistani men called their penis their "Imran Khan". All of which is impressive stuff; even more so considering that Khan simultaneously maintained a Test batting average in the high 30s and a bowling average in the low 20s — better than his all-rounder contemporaries Ian Botham, Kapil Dev and Richard Hadlee. 

What we had little idea of then was that Khan had mastered the dark art of reverse swinging the ball. He also claims that he never touched alcohol in Tramp, only coffee. Khan's greatest triumph was leading Pakistan to World Cup victory in 1992. The party in his homeland lasted for weeks, which was something, even for him.

Gary Player

Where Player is involved, it's not just his clothes that are mostly black and white. His brother, leaving South Africa to fight for the Allies in World War II, made the nine-year-old Player promise to always keep in shape. Now 80, he still exercises five times a week, including one-legged squats and 1,000 mixed crunches with weights on his chest. That quote about "the more I practise, the luckier I get" — that's him, or so he insists (it's been credited to numerous sources from Confucius onwards). But there's no doubt he has lived determinedly by that maxim. Player has also, less enduringly, trademarked the tag of "the World's Most Travelled Athlete" to describe himself. So, 15m miles later, what's his advice on air travel? Stick two large pillows under your back and a briefcase under your feet, so it's like you're lying on an ironing board. Though, he concedes, it does help if you're 5ft 7in.

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Joe Namath

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There had been dandies before Broadway Joe, a free-wheeling quarterback who played mostly for the New York Jets in the Sixties and Seventies, but few athletes have gone as far. His signature look was defined as he watched from the sideline: a full-length fur coat (mink and chinchilla were his preference). The NFL banned this practice — you have to wear dorky league-approved apparel now — but designers such as JW Anderson and Lanvin's Lucas Ossendrijver still seem to be taking note.

Namath won one Superbowl, but he was always more than his stats. He was an iconoclast: one who changed the NFL and perhaps the wider world of sport. He wore coloured footwear before everyone else, eschewing the standard-issue black high-tops for low-cut white boots. "I don't know whether I prefer AstroTurf to grass," he once said — a line that would later be spoken by Rodney Trotter in Only Fools and Horses: "I never smoked AstroTurf."

Giovanni Battaglin

Cycling fans are a perverse bunch. We respect the truly formidable champions (Merckx, Lance Armstrong) but the riders we love are the flighty, underachieving ones. And few are more flighty or underachieving than Italian climber Battaglin. When, aged 21, he finished third in his debut Giro d'Italia, he seemed a logical heir to Merckx. But Battaglin never fulfilled his promise until 1981, when the 30-year-old won two Grand Tours, the Vuelta a España and the Giro, in just 48 days. It was some achievement, made more impressive by the fact that then there was only three days' gap between races, and the Vuelta had no rest day. (The schedule seemed to encourage the riders to take drugs, and most of them obliged.) Putting cynicism aside, though, Battaglin's ascent of Tre Cime di Lavaredo and his final-day time trial to hold onto the maglia rosa have become legendary rides in Giro history — though, true to form, he'd never return to such heights again.

George Best

Once funny, there's now something tragic about George Best's most famous quips: "In 1969, I gave up women and alcohol. It was the worst 20 minutes of my life"; and, "I used to go missing a lot... Miss Canada, Miss United Kingdom, Miss World." For those of a certain age, he's the guy who turned up drunk and jowly on Terry Wogan's chat show, not the lean, deeply handsome player (in the original sense of the word) who won the European Cup for Manchester United against Benfica in 1968. Locked at 1–1 in extra time, he dances round the keeper to set United on the way to victory. But there's a quote about that night that shows he once did take pleasure from his sublime talent. He recalls how he used to have a dream where he goes past the keeper, drops to his knees and impudently heads the ball into the net. "Against Benfica, I nearly did it but then I chickened out. I might have given the boss a heart attack!"  

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