Why Michael Clayton is George Clooney’s greatest achievement

Good looks and a conspiratorial edge – Tony Gilroy’s paranoid thriller made the best-ever use of the star’s talents

George Clooney’s face in the Noughties was a curious thing. It was handsome, obviously – the most stereotypically swoonsome leading-man mug Hollywood had at its disposal that decade. But like Sean Connery’s in the 1960s, the angles of its handsomeness had a conspiratorial edge. 
He looked like a man who was not only familiar with the secret structures that held up the world, but could move through them with leopard-like ease. From the Las Vegas casino business in Ocean’s Eleven to the Californian divorce courts of Intolerable Cruelty, Clooney’s characters always knew the deep-down score – and could typically skew it to put themselves ahead. 
But towards the end of the decade, that face finally met a conspiracy even it couldn’t charm its way through – and it resulted in Clooney’s finest role to date.
Michael Clayton felt, for a stretch, like one of the Noughties’ best half-forgotten studio films. 
Released by Warner Bros in the autumn of 2007, it was a tidy commercial hit, and was nominated for seven Oscars the following year. On the night, however, it was eclipsed by two chest-beating rivals, No Country for Old Men and There Will Be Blood. And while both of those titles were both quickly afforded prime berths in the millennial film-bro canon, Tony Gilroy’s ambiguous thriller was left in reserve.
But like Clayton himself – a former litigator turned fixer for a major Manhattan law firm, enmeshed in a series of interlocking crises – the film has since built a unique niche for itself regardless, working quietly away behind the scenes. A year after its release, the banking crash bit, giving its account of the corporate world a sickeningly timely sheen. 
Ever since, and with increasing regularity, it keeps popping up as a cultural talking point. It’s impossible to watch Wolfs, Clooney’s new buddy comedy on Apple TV+, without it springing to mind. In Jon Watts’s film, he and Brad Pitt play a pair of below-the-radar ‘clean-up men’ who reluctantly pool their skills while straightening out a New York underworld fracas.
Elsewhere, in a recent interview to promote his new Netflix thriller Rebel Ridge, Green Room director Jeremy Saulnier name-checked Michael Clayton as one of two major inspirations, alongside First Blood: “It’s this very cool, modern aesthetic, very detailed,” he said. 
Meanwhile, the creators of Sky TV’s hit banking drama Industry, Mickey Down and Konrad Kay, have made no secret of their admiration, and jokingly teased the impending fourth season as “Michael Clayton in London”.
In short, Michael Clayton pulled off the rare half-trick, half-fluke every great film must: it aged well. Yet even back then, when Gilroy was riding high on the success of the original Bourne trilogy – he wrote or co-wrote all three, artfully twisting their plots away from those of the original novels – this dirty-fingered thriller was few people’s idea of a bankable follow-up. 
In fact, Gilroy had conceived of it pre-Bourne, while working as an in-house screenwriter for the production company Castle Rock, who had liked the premise and commissioned a script. Like Clayton, Gilroy was a seasoned fixer, and in the late 1990s had also spent a year working for Jerry Bruckheimer, buffing and honing the screenplays of such dainty art-house blooms as Armageddon, Bad Boys and Enemy of the State.
This, meanwhile, was a paranoid thriller written in the 1970s tradition: one man, on peeping behind the curtain, realises the climate of crippling anxiety that surrounds him is, if anything, not quite crippling enough. But in a few key respects, it was also a deeply personal project. 
Gilroy’s father, the playwright Frank D Gilroy, was a compulsive gambler like its lead – who, like Gilroy himself, was also one of three sons whose professional lives became intertwined. (His brothers are the screenwriter Dan Gilroy and the editor John Gilroy, who cut Michael Clayton.) Even the terrain was familiar: Michael’s brother’s house was located barely 200 yards from Gilroy’s own childhood home in upstate New York.
When Gilroy’s script did the rounds in the early 2000s, it soon found champions in the business: notably Sidney Pollack, director of Three Days of the Condor, one of the paranoid thriller form’s all-time peaks. (Pollack would go on to play the talismanic role of Marty Bach, the managing partner at Clayton’s firm.) 
But in attracting leading men, it had less luck. Denzel Washington turned it down, wary of Gilroy’s lack of directorial experience, while Clooney himself had to be wooed over the course of six years. At one point, a cut-price version almost went into production starring a then-pre-comeback Alec Baldwin. But Gilroy held firm for Clooney, whose Atticus Finch-like air of tawny rectitude he looked forward to grubbying up. Fortunately, a change of agents got him a meeting, and the actor came aboard.
At an early screening at Warner Bros, executives were dubious. “Who is this film even for?” one groaned in the meeting afterwards. Dan Feldman, the studio’s distribution chief and Gilroy’s main champion at the time, piped up: “It’s for men who know they’re going to die.”
This was true – but not much of a marketing line. Warner Bros realised, though, that they could sell Michael Clayton as a glossy legal thriller in the John Grisham vein. Yet as in its true spiritual forerunners – anxious conspiracy thrillers of the 1970s, like Klute and The Parallax View – that polish is a mask. 
That’s why Swinton – who deservedly won an Academy Award for her work as a grubby general counsel for a white-collar law firm – is simultaneously the closest thing Michael Clayton has to a conventional villain, and also not a conventional villain at all. Her Karen Crowder has had the ethical nutrients so thoroughly leeched out of her by her work that she’s no longer separable from the sociopathic corporate processes she abets. 
You can watch her nab her Oscar in real time in the startling (and horribly funny) scene in which Karen – on backside-covering autopilot – surprises herself by ordering an honest-to-God assassination, all because the job apparently demands it. 
As Pollack quite reasonably splutters after Clooney raises the direr implications of defending a company whose weedkiller is responsible for 400 plus deaths: “This is news? This case reeked from day one. Fifteen years in, I’ve got to explain to you how we pay the rent?” 
The structures behind structures in Michael Clayton are a prison – even for its title character, despite the fact he’s jangling some of the keys. Only three creatures are truly free here: the trio of horses serenely grazing on the brow of a hill, which Clooney encounters in the flash-forward prologue. 
In another life, the film seems to suggest, that might have been him, able to bolt at the first sign of trouble and never look back. But the trap he helped build has him tight in its teeth – which 17 years on, feel even more fearsomely bared.
Wolfs is in cinemas now
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