Given the wealth of great movies that were released back in 1999 and the general 1990s-era tastes of the Academy Awards, it was probably inevitable that the year’s Best Picture winner wouldn’t work as a satisfying long-term historical record of excellence. But it still feels galling that one of the best movie years of the past few decades somehow wound up with the darkly comic, semi-satirical suburban-angst drama American Beauty as its representative. In the year of The Matrix, Being John Malkovich, and Magnolia, among others, the Oscar goes to a movie about how a cartoonishly put-upon suburban dad gets a new lease on life when he realizes he wants to fuck his teenage daughter’s best friend? Another classic Academy blunder!

Most contemporary Oscar backlashes, though, are well underway by the time the nominations are announced; American Beauty seems to have taken a bit longer to curdle in the minds of film lovers. Its current also-ran status is striking because back at the end of 1999 and into early 2000 when the awards were held, American Beauty was, if anything, a hip year-end choice, at least relative to the options given. It followed many years of period-piece winners (the first fully present-set Best Picture since Silence Of The Lambs); it was the feature debut for director Sam Mendes and screenwriter Alan Ball; its closest competition was generally considered to be The Cider House Rules, a movie that could make just about anything look fresh and exciting by comparison.

Released as it was before a relative youthquake in the field of film criticism, American Beauty wasn’t just a hit and an award-winner. It was a critical favorite, too. Roger Ebert awarded it four stars; plenty of other smart critics were similarly moved. I wasn’t a professional critic back then, much less part of any awards-giving body. But I can testify that as a movie-obsessed list-maker, I was moved, too, enough to see American Beauty four times in the theater and place it way up on the year-end list that I composed solely for the purposes of emailing to friends and family. Suffice to say that when I made a new top 15 for the A.V. Club’s 1999 Week, American Beauty didn’t make the cut.

Even setting aside the 1999 movies I missed at the time and those that grew further in my esteem since then, there are plenty of reasons to omit American Beauty 20 years later. There’s the superficial discomfort of watching Lester Burnham (Kevin Spacey) lust after a teenage girl—not because it is behavior the movie endorses, but because Spacey himself has since been alleged to have preyed upon teenagers. That storyline, like so many others in the film, is rendered with a heavy hand, lingering on Lester’s rose-petal-filled reveries over Angela (Mena Suvari), and chased with genuine sexism in the way that Lester receives depth and shading not afforded to his even more caricatured wife, Carolyn (Annette Bening). This leads smoothly into the movie’s parade of sometimes-smug suburban-reversal clichés: The cheerful wife is a status-driven careerist hanging by a thread; the girl who presents as slutty is actually a virgin; homophobes are secretly gay.

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These are some cues among many that American Beauty’s entire orientation is very 1999, especially in the way that we’re meant to feel empathy for the emasculated, ennui-stricken middle-aged white man. The audience is supposed to cheer him on for happily taking the kind of low-wage job that other people need just to make ends meet—not to mention for cathartically chewing out his materialist wife. (Especially insidious is the fact that Spacey, whatever his personal faults, is a peerless issuer of condescending tell-offs, even when the writing itself is second-rate.)

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In a time of relative prosperity in America (or at least, a time when the extent of widening wage gaps had not been fully absorbed into popular narratives), these moments felt, at least to some, plugged into the zeitgeist; plenty of “important” movies of 1999 were expressing a similarly brewing anxiety that anticipated certain cultural divisions but now looks, honestly, a little frivolous. (This is why you’re mad? Because your wife doesn’t want you to spill beer on a couch?) American Beauty was released just about a month before Fight Club, which has similar concerns, sharing that disdain for furniture along with a strikingly similar fantasy of white-dude corporate rebuke: Both Lester and Edward Norton’s unnamed narrator blackmail their soulless white-collar employers for a year’s salary, situations calibrated to provide both plot-expedient comfort and smug moral superiority.

Fight Club, even given some of the misreadings by its most misguided fans, at least acknowledges how this moral superiority can metastasize into fascism. It also boasts a keener understanding of how stifling and soul-killing corporate America can be, and a funnier way of expressing its frustration with middle-class respectability. American Beauty, meanwhile, falls somewhere between sitcom and soap opera—both in its sensibility, and its chronology within the career of screenwriter Alan Ball, where it appears after his stints on Grace Under Fire and Cybil and before his darling-of-HBO phase of creating Six Feet Under and True Blood. Its place in Ball’s filmography may be why its influence on other movies feels limited to other quasi-satirical projects that purport to tear down the suburbs’ façade of conformity (presumably a façade that was re-erected multiple times in the years since The Graduate, The Stepford Wives, Blue Velvet, Heathers, and so on). In other words, American Beauty spawned a decade’s worth of second-tier entries from any given Sundance—movies that boldly “satirize” aspects of American life that regular old teenagers have been casually knocking for decades.

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Yet it’s also that teenager-friendly obviousness that gives American Beauty some value both as a film and as an artifact of 1999, even if it doesn’t belong on a best-of list. As the movie’s reputation has soured, it’s become particularly easy to cringe at the quiet confidence of the Burnhams’ next-door neighbor Ricky Fitts (Wes Bentley) as he courts Lester and Carolyn’s daughter Jane (Thora Birch). The amateur videographer’s monologue about the most beautiful thing he’s ever recorded—a plastic bag blowing in the wind—has flipped from the movie’s defining philosophical centerpiece to its nadir, quoted almost exclusively in mockery for at least the past decade.

But as insufferable as Ricky comes across today, and as much as he sometimes nudges Jane aside in the narrative, the scenes with the teenagers do have the ache of sincerity. That’s not the same thing as verisimilitude, and Ball doesn’t write particularly convincing dialogue for his teen characters. But in an era where teen movies were redefined as self-conscious pop-punk covers of John Hughes movies, American Beauty bridged fashionable ’90s cynicism and post-millennial sensitivity. Even if most of the characters are defined through Lester, Mendes and Ball do show empathy for just about everyone on screen, and that’s especially noticeable when their focus turns to the younger characters, who aren’t actively seeking out rebellion so much as some combination of autonomy and stability. (Jane, to the screenplay’s credit, immediately clocks her dad’s awkward lasciviousness toward her best friend.)

Interestingly, the rift between Jane and her parents doesn’t feel generational, even though she’s very much a millennial (as is Ricky, anticipating the banalities of online video and social media). Intentionally or not, American Beauty re-stages a clash between baby boomers and generation X—between characters who are basically the same age. Lester and Carolyn, both in their 40s in 1999, are late boomers on the cusp of X, and they react to their own dissatisfaction with different generational touchstones. The music that Carolyn insists on playing during their miserable family dinners, and later sings triumphantly in her car, throws back to pre-boomer crooner pop (“This Lawrence Welk shit,” as Lester calls it) that would not have been especially in vogue during her ’60s and ’70s upbringing. Lester may go back to the (mostly white and male) rock music of his youth, but his suburban rebellions—quitting his job rather than subjecting himself to a performance review, rejecting ambition, trying to stay true to what he sees as his authentic self—read as stereotypically gen X, with a sprinkling of libertarian selfishness.

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There’s myopia in the way American Beauty’s ginned-up quasi-generational conflicts play out in the foreground while affecting younger characters are relegated to supporting (if admittedly important) roles. But while staged boomer-versus-millennial conflicts have since grown in prominence while gen X has largely been shoved aside, the inability of the movie’s boomer characters to step out of the spotlight seems downright prescient today. It might be a stretch to call American Beauty elegiac, but the bittersweetness of its final moments—of Lester’s scraps of memory as he takes a bullet to the brain—does linger, helped along (as is the whole film) by the well-composed clarity of the images composed by Mendes and cinematographer Conrad Hall. In these moments, it becomes easier to read the movie as reflecting on the impermanence of any generation’s self-important narrative, rather than a glorification of a newly enlightened white boomer meeting his tragic end.

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This was not the last stand for boomer-driven prestige pictures; just this year, Green Book offered a touching story about how it’s never too late for people with outdated, misguided ideas about race and society to win the Academy Award for Best Picture. But based on widespread derision and even its healthy but unspectacular box office, a movie like Green Book is now something of a niche item. American Beauty, with its foulmouthed teens, newfangled video technology, and multiple synonyms for masturbation, felt a lot edgier than Cider House or The Green Mile in 1999, but it turned out to be a dying breed—a non-period comedy-drama that lots of adults actually paid to see in a movie theater. What makes it seem like a phony representation of its year is also what makes it feel like an authentic expression of middlebrow sensibilities. It runs 1999 angst through a filter of mainstream accessibility. Isn’t that what The Matrix does, too?

Of course, it’s not fair to award American Beauty full marks just for trying to make non-genre entertainment, or for accidentally evoking the year it was released. This is not a movie that feels timeless today—and looking back, not one that was particularly groundbreaking in its own time, either. Yet it does contribute to the tapestry of 1999 cinema a vision of “perfect” baby boomer prosperity being dismantled—belatedly, imperfectly, non-definitively, maybe even self-aggrandizingly, but dismantled nonetheless. Without leaning heavily on youth-culture trends or obvious signposts of its era, it has nonetheless become very much of its time. Timelessness is a wonderful (and slippery) quality in cinema, but not a particularly common one. Must movies become cable-rewatch staples, living far beyond their initial moment, aging as little as possible? They can also be disposable, shallow, and still somehow capable of sticking around, like a plastic bag turning in the breeze.