Before George Best, footballers were humble, meat-and-potatoes men, far removed from the rarefied worlds of fashion and advertising they later came to embrace. After George Best, they were playboys, male models, and even — regrettably — pop stars. Tracing the marketing of football cool from George Best to David Beckham, Richard T Kelly remembers the man who kicked the whole thing off, football's first authentic superstar pin-up.

Cristiano Ronaldo, when asked once for his view on who were the world's three best footballers, replied breezily, "I am the first, second, and third." Later put on the spot about why opposing fans jeer him, Ronaldo riposted, "I think that because I am rich, handsome and a great player, people are envious of me."

While one can't really dispute how richly Ronaldo has been blessed, the level of self-love does jar a bit. Does it remind you of anyone? I find myself thinking of Kanye West, known at moments of over-excitement to declare himself "the number one human being in music" and "the greatest living rock star on the planet."

But to be fair, as the pundits say, you can see why elite sportsmen, just as much as megastar musicians, might get a few big ideas about themselves. The clue is in "elite". To their proven gifts for performing on a big stage, combine the noughts on the end of the weekly wage. Add to that the calibre of partner you command, and the showbiz gods you will get to know socially. Throw in, too, the brand endorsements you accrue, the gloss these put on your own brand, the top clobber you're given for free — and you could easily persuade yourself you're a rock'n'roll star. God forbid, you might even make a record.

This is how Paul Gascoigne — who confessed he was "not really a big music man" — came to release a "rap" version of Lindisfarne's "Fog on the Tyne". Ashley Cole never inflicted any music on us, yet when he posed beside Cheryl in white strides and shirt split to the waist, supposedly to promote the National Lottery, he was clearly basking in reflected pop glory. As with Gazza, this was a crushing failure of self-awareness.

Is the lesson, then, that top footballers ought to leave their creativity on the pitch, reject all recording contracts or modelling offers that come their way, and shun the company of the pop world, lest they end up looking irredeemably uncool? Well, no — because, once, one man did all of that stuff with such panache that he had all the top pop stars wishing they were him.

"I have always thought I was the best ever player," George Best told FourFourTwo magazine in 2001 when he was 55 years old. But to this day, Best's ball skills, his fiery gift for spinning and surging past Earthbound defenders, still have a supreme look about them. As his Manchester United manager, Matt Busby, testified: "I have never seen a player who can beat a man — or men — so close, and in so many ways." Best did it, moreover, with the old leather balls on the old heavy pitches where opposition cloggers could still tackle him from behind. As such, his elegance seems even more otherworldly.

Best's talent earned him all sorts of proposals, but Busby managed to block him from taking up a lucrative offer to cut a record. Instead, Best inspired a 1970 hit, Don Fardon's "Belfast Boy", its Hammond organ and fuzzy guitars driving a lyrical tribute to Best's pop-art appeal: "'Cos you move like a downtown dancer/With your hair hung down like a mane". His physical beauty was a crucial part of the package: Germaine Greer, working in the Manchester media scene in 1968, was hardly alone in noticing his "heart-breaking Irish eyes" when she met him. All these attributes were the making of football's first authentic superstar pin-up.

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Best\'s endorsement of Stylo Matchmakers football boots, 1969

Best was a cultural product of the Sixties, but his looks and gifts were so exceptional that 50 years on, they have a timeless ring about them, akin to The Beatles' White Album or Sean Connery's Bond. Noel Gallagher, another Mancunian with a sound ego ("McCartney, Weller, Townshend, Richards — my first album's better than all their first albums"), paid his respects by putting Best on the cover of said first album, Definitely Maybe in 1994. "He owned a nightclub and a clothes shop, drove a Ferrari and he shagged Miss World," Gallagher enthused. "The only thing he didn't do in his life that was cool was play music, and he probably would have been good at that, too." For the rest of us, though, it's a good thing that Best for once knew his limits.

A famous cautionary tale attaches to the Best legend nonetheless, since it ends with his alcohol-stricken death in 2005. Other footballers followed where Best led but played it safer, and enjoyed more lucrative (if less iconic) careers. So what is the truly cool way to do it? It maybe depends where you stand on the assertion of Neil Young's anthemic "Hey Hey, My My (Out of the Blue)" — quoted by Kurt Cobain in his suicide note, and also covered by Oasis, among others — that "it's better to burn out, than to fade away".

We know the Sixties so well today because the decade produced so much pop-cultural evidence. Liverpool fans on the Anfield terraces really did sing Beatles songs. Those terraces had their own culture, but in the Sixties it was changing rapidly. National Service was abolished, working-class lads no longer looked like scale models of their dads. There was an appetite for newness and television was a window on it. The Beatles, above all, offered a new model of "working-class made good".

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Best controlling a football as fiancée Eva Haraldsted (right) and other girls of the Blinkers United charity football team look on, 1969

Previously, professional footballers had led much the same lives as the supporters. On Saturdays, Newcastle's Jackie Milburn worked a shift at Ashington Colliery then took the bus to St James' Park to play. Liverpool legend Albert Stubbins (soon to pop up on Peter Blake's sleeve for Sgt Peppers Lonely Hearts Club Band) earned £12 a week like most other players. But in 1961, the players' union voted down football's wage ceiling of £20 per week: a sudden show of player power, a sign that footballers had a notion of what they were worth. That same year, 15-year-old George Best left Belfast to sign pro forms at Manchester United.

By 1965, old cotton-town Manchester was in the midst of a painful deindustrialisation, and its people weren't rolling in disposable income. But a ticket to Old Trafford to watch United, the league champions, was a couple of quid in today's money, and there, close at hand, you could witness a truly aspirational figure. Best had been the fans' favourite since a classic game at Chelsea in 1964 where he ran rings round a defence led by Ron "Chopper" Harris. Teammates like Bobby Charlton were less keen on Best's reluctance to pass the ball. (Like the most talented kid in the schoolyard, Best knew that giving it away was a waste.) But self-regard was part of Best's appeal. Morrissey, an unlikely boyhood visitor to Old Trafford, would write in his autobiography of how Best struck him as embodying "the shocking new against Charlton's Fifties pipe-smoking discipline".

When off-duty and cruising Manchester's discotheques, Best for a time affected a Beatleish look (suits, boots and fringe) but soon he was experimenting with his wardrobe like a proper little mod. No "Dexies" or purple hearts for Bestie, though: he remained a Belfast man who drank beer and shorts when out on the town for the night.

In 1965, the BBC's Top of the Pops cameras picked out Best amid a studio audience watching The Rolling Stones mime to their hit single "The Last Time". While Mick
Jagger tries out his preening moves, Best stands, darkly handsome but wary, seemingly waiting, maybe to approach a girl he's spotted, or to get outside of a glass of something cold at the bar. He exudes the special shyness of one who's deeply vain, quite sure the whole room is looking at him.

Back at work, Best sealed his legend in Lisbon in March 1966: a European Cup quarter-final against Benfica. Best tore into the opposition, scoring twice in the first 15 minutes. The Portuguese papers regarded him as a pop star, and the British press embroidered their refrain, "El Beatle". Suddenly not so shy, back at Heathrow, Best stepped off the plane sporting a souvenir sombrero. Incredibly, he looked cool.

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\'El Beatle\

Best opened a boutique, Edwardia, in 1967 with his mate at Manchester City, Mike Summerbee. He would later declare that the business "was just another way of pulling birds": Edwardia had a handy upstairs flat and Best used it to entertain ladies during the afternoon. He had to fight off the female attention, since girls would come to Old Trafford just for him. "I noticed," said Best, "that when I touched the ball on the field you could hear this shrill noise in the crowd with all the birds screaming like at a Beatles concert." The audible worship, Best further admitted, would often give him an erection.

Best had the flash motor; first a Jaguar saloon, then a Lotus Europa, E-Type Jags and more. He added the blonde fiancée (though his engagement to Danish student Eva Haraldsted was so fleeting she sued for "breach of promise"). Eva was succeeded by a Swede, Siv Hederby, another delectable creature rather ill-used. (With maximum lack of gallantry Best boasted of being "very partial to Scandinavian crumpet, it being generally beautiful, always willing and a bit thick...")

By the end of the Sixties, Best was earning £2,000 per week (the national average then was £23.) What really lined his pockets were extracurricular activities: the ghosted newspaper column, the modelling, the endorsements for hair tonic, chewing gum and Stylo Matchmakers football boots. As handsomely as it paid, Best looked askance at the remorseless marketing. In this, as in other ways, he mirrored The Beatles and their bored, sarcastic view of the rising tide of tat to which they had put their names and likenesses: figurines, mop-top wigs, comic books. But then, who except The Beatles understood the pressures of being them? As Mike Summerbee would later muse, "I can't imagine how difficult it must have been to be a person like George Best."

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At his Best Boutique in Sale, 1966

In 1969, Best hired the architect Frazer Crane to build him a luxury bachelor pad with all mod cons, 10 miles outside Manchester. For Best, it should have been the peaceful retreat that the Surrey mansion Kenwood was for John Lennon; instead, the football icon became irked by the house's gadgetry and the crowds of rubbernecking fans outside (a young Noel Gallagher among them.) The house just confirmed Best's sense of living in a goldfish bowl, and within three years he sold it.

Best didn't want a designer life. His true tastes were traditional working-class Belfast, perfectly itemised by novelist and Best biographer Gordon Burn as "the bird, the boozer, the puzzle book and the gee-gees." Simple pleasures, and a dream of sorts for a certain type of lad — but it wasn't what Best's image was meant to be selling. Moreover, one of those pastimes was becoming consuming — and it wasn't "screwing", as he charmingly called it. Rather, love of the bottle was about to swallow all else. And Best's decline made a vacancy for a new pop-star footballer, one who knew better how to stay out of bother.

When Kevin Keegan first met the girl he would later marry — at Doncaster's St Leger fair in 1970 — he was too abashed to tell her he played football for Scunthorpe United, describing his summer job at a steelworks instead. A shrewd move, as it went, for Jean Woodhouse's idea of a fanciable footballer was George Best, but Keegan had a fair-sized football talent of his own and even bigger ambitions. In 1971, he made a dream move to Liverpool, soon making himself a top player and a hero to the Anfield crowd. But he was not nearly satisfied.

As teammate Phil Neal recalled, Keegan "woke up to the potential of the game sooner than many better players". By 1972, he had formed his own company, cut his first single called "It Ain't Easy", put his name on some plastic footballs and a newspaper column, and was opening supermarkets countrywide. All while George Best's ambitions looked to have dissipated, the monotonous habits of the drunkard taking charge. In May 1972, Best repaired to Marbella and briefly threatened retirement. That November, in a nightclub fracas, he fractured a girl's nose. The press could smell he was going off the rails. That much was undeniable by 1973 after Best had opened a nightclub called Slack Alice, a roaring success where he set about drinking the proceeds.

That summer, Keegan took careful note of how the older man was managing his career. Indeed, Keegan's first memoir would feature a chapter entitled "Lessons from Bestie". Stressing his respect for Best the player, Keegan made clear a top professional shouldn't squander his talent as a barfly. "As soon as I was in demand to attend functions or endorse products," wrote Keegan, "I set out to conduct myself differently from Bestie. I tried to learn from his mistakes." In November 1973, Stylo the bootmakers decided Best was no longer a suitable ambassador and replaced him with Keegan. Six months later, Best was finished at Manchester United, his career effectively shot at 27, that age of rock-star infamy at which Brian Jones, Jimi Hendrix, Janis Joplin and Jim Morrison — and more recently, Kurt Cobain and Amy Winehouse — all died.

So, Best decamped to Los Angeles to play in the North American Soccer League. For fun he would kick an occasional ball about with his mate Rod Stewart, an exile from the British Labour government's 83 per cent top tax rate. But mainly Best stewed himself in booze. By 1982, he was bankrupt and by '83 utterly spent as a player. His image retained tabloid value — he could still bed a beauty queen — but he had to toil harder for smaller returns. A singing voice can weather abuse far better than an athlete's body, and while drinking and shagging kept Rod Stewart's career relatively lively for many years, they spelled death for George Best's.

Keegan, just as averse to top bracket income tax as Rod Stewart, finally landed the big payday for which he had grafted when he moved to Hamburg, Germany in 1977. With his customary drive, Keegan made Hamburger Sport-Verein the Bundesliga champions, while maintaining the prosperous business of himself: endlessly attending photoshoots and TV studios, and lending his merchandising name to lollipops and boardgames.

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Kevin Keegan advertises the Grundig Hit Boy Radio, 1980

So, when his HSV teammate Ivan Buljan introduced him to a music producer and suggested it was high time he cut another pop record, Keegan simply slotted it into his schedule. The song was "Head over Heels in Love", a pedestrian ballad by the Yorkshire pop band Smokie (of "Living Next Door to Alice" fame). Keegan, in a rare commercial misstep, accepted a flat fee of £20,000, but promoted the disc so keenly it made the German Top 10 and the UK Top 40. He mimed the song on German TV with his arm round a hausfrau in the studio audience, confirming the family-friendliness of his image.

If Keegan had outpaced Best in the pop charts, his credentials as a style icon were a good deal weaker. In 1980, he modelled the Harry Fenton menswear shop's Kevin Keegan Collection with a shade too much polyester, while his curly perm kicked off a trend of sorts around club changing rooms, but not on the terraces. There, a growing punk-like fanzine culture and the rise of the "casual" movement had been growing throughout the Seventies. The gulf between players and fans — in earnings, fashions and aspirations — was starting to yawn wide.

The casuals could look cool in branded track-suit tops, jeans and tidy trainers. But by the mid-Eighties, footballers seemed to believe that "going for it" on the fashion front meant a mullet or bouffant hairstyle and a pastel jacket like Don Johnson in Miami Vice. Epitomising this look were Glenn Hoddle and Chris Waddle of Tottenham Hotspur, two flair players who were by no means bad-looking lads. And yet, fatally fancying themselves as vocalists, they teamed up with a songwriter who had penned a few hits for The Nolans and The Dooleys to record the thudding "Diamond Lights", which they mimed on Top of the Pops in April 1987, Waddle at least having the grace to look sheepish. Smash Hits magazine had already declared of the Eighties that it was "like punk never happened" but, for those who felt football could be a thing of beauty, it was as if George Best hadn't lived.

The 1990 Football World Cup is a landmark in the game, not least because it brought forth the world's first non-cringeworthy football song: New Order's "World in Motion", which, alongside England's surprise-package showing at the tournament, kick-started the game's popular revival (plus the fleeting musical career of English attacking midfielder Paul Gascoigne.)

That revival, though, came at the cost of the Premier League in 1992, and the Sky TV cash that changed football. Today, every top-flight player earns crazy wages, even down to the bench-fodder at the mid-table clubs. They are elite athletes, aspirational figures in playgrounds nationwide but there is not one among them who seems "chosen", as George Best undeniably was. Manchester United became the standard-bearers of the Premier League era; yet, as with its rivals, the club's true genius players have mainly been foreign imports (Cantona, Ronaldo), while its outstanding home-nations talents (Giggs, Scholes) have not inspired a wider cult. Except for one.

Of Alex Ferguson's Class of '92 youth players who slowly infiltrated Manchester United's First XI, David Beckham did not seem nailed on to excel. As late as 1999, George Best passed a dismissive verdict on Becks: "He can't kick with his left foot, he can't head a ball, he can't tackle and he doesn't score many goals. Apart from that, he's all right." Beckham, though, exhibited a Keegan-like work-rate in the cause of his self-advancement. It's as if Beckham, via Keegan, took his own lessons from Bestie.

Beckham found a popstar wife in the most entrepreneurially inclined Spice Girl. Though a hip-hop fan, he shrewdly avoided cutting a rap record, but proved he could pass himself off in a Gaultier sarong or posing in little underpants for Armani. His regular haircuts became tabloid news. In short, he did majestically well, and has retired at leisure to his menswear Modern Essentials Collection for H&M and the upscale leather jackets he endorses for Belstaff.

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David Beckham, with then-girlfriend Victoria \'Posh Spice\

Writer Aleksandar Hemon has called Beckham "the most overrated and overpaid player in the history of sports". But we should all be so lucky. George Best insisted to the bitter end that his mistakes were his own, that he had wanted no other life. Still, in the view of Best's old mucker Mike Summerbee, "People like David Beckham should look to George and his memory and say, 'Thank you very much.'"

Richard T Kelly's novel The Knives is out on 4 August; his dual biography, Keegan &
Dalglish, will be published in 2017