Open this photo in gallery Fight Club is a dark satire that focuses on Edward Norton, left, as an office worker and Brad Pitt, right, as a charismatic radical. Merrick Morton/Twentieth Century Fox via Reuters

“Oh, I get it. It’s clever. How’s that working out for you? Being clever?”

So asks Brad Pitt’s Tyler Durden of Edward Norton’s nameless narrator about 15 minutes into Fight Club. The wink-nudge exchange, one of countless fly-by witticisms laced into Jim Uhls’s adaptation of Chuck Palahniuk’s novel, highlights the narrative bobs and weaves yet to come in director David Fincher’s film. But the line also acts as an unintentional pre-emptive meta-query of Fight Club’s own legacy. As in: How has that cleverness worked out, exactly, 20 years later? The answer: far better, and messier, than anyone could have possibly imagined.

Released two decades ago this week, on Oct. 15, 1999, Fight Club didn’t so much pummel Hollywood as get beaten down by it. Its world premiere at the Venice Film Festival was greeted with a chorus of boos. (“Literally the guy running the festival got up and left,” Pitt recalled years later.) The industry media was openly hostile, with the Hollywood Reporter running a column that said the film “will become Washington’s poster child for what’s wrong with Hollywood. And Washington, for once, will be right.” Critics across the approval matrix slammed it (the Los Angeles Times called it “a witless mishmash of whiny, infantile philosophizing” while The Wall Street Journal, perhaps more predictably, complained that the film “reeks with condescension.”) First-run audiences mostly ignored it, with the film opening to US$11-million, only narrowly beating the fourth-week gross of the Ashley Judd thriller Double Jeopardy. Fight Club, intended to be the triumphant re-teaming of Pitt and Fincher, whose serial-killer thriller Seven was a worldwide sensation just four years earlier, would leave theatres barely earning back half of its US$63-million budget.

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Timing, though, is everything. The deeply dark satire, focusing on an office worker bee (Norton) who teams up with a charismatic radical (Pitt) to start an underground fighting society that quickly morphs into an anarchist movement, came into the world with the nihilistic violence of Columbine fresh in the cultural memory. Studio Twentieth Century Fox, then in the midst of corporate war games, mismarketed the work as a fist-pumping action movie. (“I had close friends say to me, ‘I haven’t seen it yet – I’m not into boxing movies,’” Uhls recently told journalist Brian Raftery, author of Best. Movie. Year. Ever: How 1999 Blew Up the Big Screen.) And the film’s detractors were loud, ruthless and unafraid of spoiling its crucial third-act twist. (Rosie O’Donnell gave the game away on her popular afternoon talk-show, a move Pitt later called “unforgivable.”)

Open this photo in gallery Helena Bonham Carter played Marla Singer. HO/Twentieth Century Fox

But it didn’t take that long for Fight Club to build an enthusiastic, disparate, often philosophically-at-odds membership. I should know – I was one of them.

At 16, I was working in a suburban Toronto multiplex, sweeping away popcorn and tearing ticket stubs, a mindless job that afforded me plenty of opportunities to see the same movies, over and over – an especially sweet job perk if said movies were restricted to those 18 years and older. During Fight Club’s first few weeks, I must have watched the movie a dozen times. Much of its subversiveness flew over my head – I was too much of a goody-goody to glom onto any of its coarser politics, and too young and dumb to realize it was critiquing the violence it was simultaneously revelling in – but the film’s eagerness to shock and appall was instantly appealing. And that twist! I spent so very many hours of my life pulling apart the reveal that (two-decade-old spoiler alert) Tyler and the Narrator were the same person, poring over the (actually overwhelming) evidence that Fincher literally spliced into the film. Were I to have a dorm room at the time, you can bet that a Fight Club poster would’ve adorned at least one of its walls.

When the movie was released on DVD in the summer of 2000, I was waiting outside my local HMV to buy a copy. As were, eventually, six million others around the world, who would help make Fight Club one of the most successful home-entertainment releases ever – and one of the most popular, misunderstood and prescient films of the 20th century.

In so many ways, Fight Club has both predicted our current, toxic zeitgeist while at the same time being directly, if unintentionally, responsible for it. So-called men’s rights activists and their “red pill” awakenings; the anti-snowflake far-right movement; the troll-in-jester guise of swampy online forums such as 4chan; the virulent ascendancy of the “involuntary celibate” crowd: All were foretold by Fight Club in one way or another. And all can, with particular blinders affixed, find common cause with Fight Club, too.

The intensely charismatic, highly styled and perfectly sculpted Durden spends much of the film whispering anti-consumerist slogans – “We’ve all been raised on television to believe that one day we’d all be millionaires and movie gods and rock stars, but we won’t” – that are at once sincere and self-satirizing, coming as they are from the mouth of, well, one of the world’s biggest movie gods. Throughout the film, there is an intense, and hilarious, push-pull tension between who modern men are expected to be, and who they actually are – the cracked result of one privileged and selfish generation’s neglectful shattering of another. But the film is, from all points of conception, a comedy. Think of the moment when Durden is being slugged by the cartoonish mobster Lou – the punches keep coming until our presumed hero is laughing maniacally, spitting blood in the face of his foe and the audience. You think that this society is a joke? Well, that’s because it is.

Open this photo in gallery Fight Club is guilty of exhibiting the kind of juvenile bro humour it otherwise repudiates. Twentieth Century Fox

Yet, since Fight Club’s release, the film’s satirical backbone has been cracked and reshaped through a series of reappraisals and misinterpretations, with the darkest of the internet’s corners treating Durden’s faux provocations as gospel. The character was conceived by Palahniuk as an effortlessly cool manifestation of the Narrator’s worst impulses, a prank of the mind that eventually becomes uncontrollable and psychopathic. As Durden begins to radicalize the impressionable young men in his orbit, and as his ideals take the physical form of guns and bombs, audiences are not meant to identify with this rabid dog of a prophet, but to become repulsed, as is the Narrator’s response. Project Mayhem, Durden’s end-game, sticks a fork in the eye of not only the huge corporations undoubtedly making life worse for the modern man, but also those who are naive enough to think that burning everything to the ground is the answer. But by pointing a finger at their audience, Fincher and company didn’t realize that so many would flip the bird right back at them, or at least their ideals and intentions.

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The filmmakers are not entirely off the hook here. A recent rewatch – my first in about five years – revealed how frequently the film slips into just the kind of juvenile bro humour it otherwise repudiates. Remember the vulgar mammaries of eventual Project Mayhem casualty Bob (played, quite affectingly, by Meat Loaf)? Or the sick liposuction scheme at the heart of Durden’s soap empire? Or the newspaper clips trumpeting, say, the “molestation” of a performance artist? All immature and gross moments that play just outside the film’s satirical bull’s eye. Briefly, it feels, Fincher is giving his audience permission to laugh at someone else, and not ourselves – the laziest route of comedy.

Mostly, though, Fight Club resonates today precisely because it refuses to do things the easy way. It is messy, and uncomfortable, and relentless in its thematic and aesthetic ambitions (it’s astounding to think of just how much time and energy was spent on so many of its throwaway sequences, such as the Narrator’s visit to his imaginary ice cave complete with CGI penguin, or the five-second scene where he fantasizes about a midair collision). Placed next to a more recent effort in distilling male anger – say, Todd Phillips’s Joker – and there is no comparison at all. I’m just as sure that we’ll still be talking and arguing about Fight Club in the year 2039 as we will have also by then cycled through at least three more iterations of the Clown Prince of Crime.

Fight Club hits you as hard as it can. Twenty years later, the bruise hasn’t faded.