Miles Davis in 1954 © Francis Wolff/Corbis
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Before he’s anything else, before he’s paranoid, or high, or dangerous, or belligerent, or vulnerable, or sad, the Miles Davis of Miles Ahead, writer-director-star Don Cheadle’s freewheeling new biopic, is cool. You can tell this from other characters’ reactions to him, which range from mild respect to outright awe; notwithstanding fear and pity, which are also appropriate. You can tell by the fact he goes by his first name only. You can tell from his chain-smoker’s rasp, his steely self-possession. You can tell by the fact he wears his sunglasses at night. Mostly you can tell he’s cool because, at least in the incarnation of Miles the film mostly focuses on, when he was 53 and down on his luck, he wears outfits that would make any other middle-aged man look ridiculous, bordering on certifiable. And yet still, he looks cool.

By all accounts, including his own, Miles really was cool. He was so cool he invented a genre of music called “cool jazz”, and later gave highest expression to it on an album called Birth of the Cool. When it came out, in 1957, he had abandoned cool jazz, leaving it to West Coast white boys such as Chet Baker who weren’t, for all their efforts, as cool as he was. (Coincidentally, there’s another new film, Born to Be Blue, with Ethan Hawke as Baker, “the James Dean of jazz”, in which it’s made clear how devastating Miles’s dismissal of a fellow trumpeter could be. Honestly, you wait years for a biopic of a dapper junkie jazz legend, and two come at once . . .)

What do we mean when we say Miles was cool? Certainly not chilled. He was angry, disputatious, sometimes violent. But the way he dressed, held himself, talked. The way he played . . . 

Miles Ahead opens in Manhattan in 1979. Miles is holed up in his brownstone on the Upper West Side, addicted to booze and cocaine. He’s been a virtual recluse for four years, during which time he hasn’t played a note. He enters the film limping — he had an arthritic hip, as well as myriad other complaints, physical and psychological. (Cheadle has said he believes Miles was bipolar. “His organism is tired,” was his colleague Gil Evans’s more opaque, and much cooler, explanation for Miles’s hermit period.) An early scene has the ageing trumpeter in an indigo and turquoise brocade frock coat, with gold buttons and a Nehru collar. His shades are as big as a scuba diver’s mask. His hair is a sort of Afro mullet. Whatever else was going on in his life, he looks magnificent.

Cheadle couldn’t have known — he’s been developing the film for almost a decade — but Miles Ahead is very on-trend: one suspects it might appeal to Alessandro Michele, the Gucci designer who promotes an exotic, 1970s-inspired aesthetic, and to Kim Jones, men’s designer for Louis Vuitton, whose current collection features pink silk-print pyjamas that could have been designed with Miles in mind.

The film then flashes back to the 1950s, a happier period in the musician’s life. He’s a different animal entirely (though still a cat, this being jazz). He’s wearing a powder blue, single-breasted suit, a white shirt and a striped tie. This was Miles’s Brooks Brothers period. Later, we see him in a double-breasted dove grey suit. His hair is short. His shoes are shiny. He looks elegant, debonair. Closer to what we think of when we hear the phrase “jazz style”: a suave American black man blowing a trumpet in a smoke-filled nightclub.

Has there ever been a group of performers more concerned with looking the part than jazz musicians? The young Miles, son of a Midwestern dentist father and a glamorous music teacher mother (whom he credited with his interest in clothes), was first impressed by the style of the jazz bands he saw in East St Louis as a teenager. In his autobiography, Miles, he writes: “All the cats in the band had their hair slicked back, was wearing hip shit — tuxedos and white shirts — and acting like they was the baddest motherfuckers in the world.”

A few years later, in New York, now playing with Charlie “Bird” Parker, he describes being buttonholed by saxophonist Dexter Gordon (“the cleanest cat around”) for not being hip enough: “I can’t be seen with nobody wearing no square shit like you be wearing. And you playing in Bird’s band? The hippest band in the world? Man, you oughta know better.” Miles saved up $47 and went to F&M’s on Broadway to buy a “grey, big-shouldered suit”.

Don Cheadle as the jazz musician in his new film ‘Miles Ahead’

It’s the music Miles was playing with Bird in the 1940s — bebop — that shifted jazz and jazz style. Breaking with the mainstream dance music, played by bow-tied swing bands, jazz became increasingly challenging, improvisational, conceptual. It was music for a late-night cognoscenti of hepcats who picked up on the cool clothes and the hip slang. In white culture, jazz was the music of the beatniks. After the 1950s Miles would never again wear a dinner jacket to play it.

He played with the best, and the best dressed: pianist Thelonious Monk; trumpeter Dizzy Gillespie; drummer Max Roach; saxophonist John Coltrane. Monk wore a beret, sunglasses, a cravat and an oversized double-breasted suit, with tapered trousers that were pegged at the bottom: not as exaggerated as a zoot suit, but not far off. The saxophonist Ornette Coleman, pioneer of free jazz, wore granddad shirts, knit caps and an unkempt beard. By 1967, Miles was as far out as anyone, wearing African dashikis, Indian wraparound shirts, patch suede trousers from black designer Stephen Burrows. His shoes were from London’s Chelsea Cobbler. He drove a yellow Ferrari. He continued to play — and gloriously overdress — until his death in 1991, aged 65.

The British, I think, are suspicious of modern jazz, as we tend to be of all subcultures that are deliberately difficult and fail to display self-mocking humour. The French fell head over baguette for jazz but that’s because, at least according to the Brits, the French are pretentious and po-faced — and also look irritatingly chic smoking cigarettes while wearing black roll-necks. (Miles spent time in Paris, of course, where he romanced the singer Juliette Gréco, also of course.)

From left: Gucci, Wales Bonner, Agnès b, Hermès ©

To my mind, the most memorable British response to the chin-scratching stylings of modern jazz was the fictional “Jazz Club”, the BBC sketch comedy The Fast Show’s lampooning of the genre, and the mortifying white jazzer Louis Balfour, played by John Thomson, in burgundy roll-neck and bowl cut, who makes egregious asides to camera in mellifluous Mancunian: “Nice!”, “Grrrrreat!”, or, simply, “Jazz”. (More recently, Will Ferrell gave us Ron Burgundy’s unforgettable jazz flute.)

In the US, as jazz moved to the margins, elbowed out by rock and pop, the wild experimentalism of the 1960s and 1970s gave way to a return to more traditional jazz. Leading players of the recent past — Wynton Marsalis, The Jazz Messengers — mostly wear slick suits on stage. But as Cheadle’s film reminds us, in its heyday, jazz offered us rock stars before rock was invented: boozers, druggers, womanisers, tearaways, bohemians, makers of brilliant music and, in Miles’s case particularly, wearers of extremely courageous trousers.

Alex Bilmes is editor-in-chief of ‘Esquire’. ‘Miles Ahead’ is out in the US; it is released in UK cinemas on Friday

Photographs: Francis Wolff/Corbis;

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