A Look Back at the 1999 (2000) Oscars
How Did the Academy Respond to One of the Most Significant Years in Recent(ish) Cinema History?
It's Oscar Sunday, and while I'd love to write a piece similar to last year's, in which I analyzed the 2023 Best Picture field for common themes and trends, the plain truth is that I haven't been able to watch all of this year’s nominees (it’s actually the fewest nominees I’ve seen pre-ceremony in over ten years. It’s probably lame to be as depressed about that as I am, but oh well). So instead, I'm going to cast my gaze back 25 years (?!) to the 2000 ceremony, which honored the films of 1999 - long considered one of the best and most important years of the modern cinema age. This is to serve two purposes - in part to see the degree to which those nominations and eventual winners properly represented such a totemic year (flash-forward: hardly at all), and in part to look back with plenty of/too much (25 years, Jesus God…) hindsight and consider what else could have or should have been included.
Heres a sample of arguably the most important/influential/resonant/enduring films released that year:
All About My Mother
Eyes Wide Shut
The Matrix
The Blair Witch Project
Toy Story 2
Fight Club
The Virgin Suicides
Magnolia
Three Kings
Star Wars Episode I: The Phantom Menace
The Sixth Sense
Topsy-Turvey
Being John Malkovich
The Straight Story
Bringing Out the Dead
The Insider
Office Space
Notting Hill
Lock, Stock, and Two Smoking Barrels
Election
The Mummy
Run Lola Run
American Pie
The Wood
The Iron Giant
The Limey
Princess Mononoke
…with plenty more that are arguably, or subjectively, more minor but still notable in some way (if only to me): The Talented Mr. Ripley, Double Jeopardy, Any Given Sunday, Galaxy Quest, Sweet and Lowdown, Sleepy Hollow, Dogma.
That’s a hell of a group, and that’s predominantly American-made films. Let’s go ahead and see what Oscar came up with that year to represent the best of that crop…
Best Picture

American Beauty - A suburban dickhead, bitter about his own life choices, decides to make his malaise everyone else’s problem as he strives to achieve spiritual freedom, defined here as smoking pot in the garage and trying to fuck a high schooler. Even back then I kind of felt like this movie was full of shit. An insane time capsule of what white people thought our biggest problems were at the turn of the millennium, and a movie that is absolutely radioactive today given its central plot device and what we know about its star.
The Cider House Rules - I remember dreading this like it was homework and coming out pleasantly surprised. I have not watched it since. Seems like total fluff in retrospect - the prototypical late-period Miramax prestige awards play - but it’s not for nothing that it’s also a passionate defense of a woman’s right to choose.
The Green Mile - I liked it at the time because I loved the book, but it’s aged like milk. I rewatched the trailer for this fairly recently and it played like absolute parody.
The Insider - A movie about the difficult and thankless task of doing the right thing, even in the face of losing your entire life over it, becomes one of the most prescient and insightful films of the last 50 years when 60 Minutes bows to corporate pressure and decides to not air their interview with tobacco company whistleblower Jeffrey Wigand. Pinpoints the exact moment that any semblance of journalistic integrity started to die forever. Far and away my favorite movie in this lineup, this has unfortunately for the world aged better than any movie up for any award this year.
The Sixth Sense - A bonafide classic. One of the last organic phenomenons - an original idea that got dumped in late August and became a sleeper hit largely due to a twist that is not just a mind-blower but is also beautifully woven into the movies core themes of healing through acceptance. It became such a phenomenon, and Shyamalan beat its style and twist-based narrative so deeply into the ground, that I think we forget how genuinely great and beautifully constructed it really is.
What in the world do we make of such an overall underwhelming line-up on any kind of analytical or even purely retrospective level? Not everything can be 1967, the year that was the subject of Mark Harris’ fantastic book Pictures of a Revolution, in which he examined that year’s Best Picture line-up as a microcosm of the various cultural and societal forces at work at that very tumultuous point in American history. If we try to apply that rubric here, what do we come up with? Can we even try to do that when there isn’t anything anywhere near as forward-thinking or era-defining as Bonnie and Clyde or The Graduate?
American Beauty certainly seems like the apotheosis/death rattle of a certain type of “the suburbs are hell” genre that flourished in the 80s and 90s and which by the 2000s had become cliche before shifting demographics and economic realties rendered it somewhat obsolete by the 2010s. Beauty is also an interesting fulcrum point in the shift to the new millennium - it’s ostensibly an edgy indy film distributed by the first new major studio in generations (the Steven Spielberg co-owned Dreamworks); the most interesting thing about the film in retrospect is the tension between the darker, more satirical original screenplay by Alan Ball and the soft edge of life-affirming sentimentality that director Same Mendes wrapped it in (listen to or read that final voice-over and tell me what movie you think it’s providing a summation of, because it’s certainly not this one). A movie like previous year’s Happiness if much more successfully doing what this movie thinks it’s doing, but it also one that would never in a MILLION years be recognized or even acknowledged by a large awards-giving body.
The Cider House Rules is something of an inverse in that it’s a very respectable and emotionally manipulative studio picture that Trojan Horses a central theme involving what was then and somehow still today the apparently controversial stance that a woman should be able to control and make decisions about her own body (addressing as it does not just abortion but sexual abuse and incest).
The Green Mile is quite regressive in its filmmaking and in its characterizations - John Coffey is a lamentable stereotype and the villains are so one-dimensional that they’re almost inside-out. It’s a syrupy melodrama that becomes pulverizing in its sheer length and lack of subtlety, and certainly feels like something that would have been a prestige picture in the previous couple of decades - it would be right at home in a mid-80s Best Picture line-up (not a compliment: go back and look at those, particularly ‘84 and ‘85 - some of the titles alone will put you to sleep).
The only two movies here that have any kind of lasting impact (and again, this is all subjective) and are thus defensible as nominees are The Sixth Sense and The Insider, though the The Insider is the only one that has any kind of social importance. Not that this is a necessity or to suggest that it disqualifies Sixth Sense from greatness - it is an impeccably-crafted Hollywood movie in the best sense, wrapping a high-concept hook around a genuine emotional core, and is perhaps the last great instance of a bonafide, come-from-nowhere smash. This was a tossed-off late-summer calendar-filler for Touchstone that people may not remember became for a spell one of the ten highest grossing movies of all time. It’s perhaps the greatest example of what it’s doing, a lightning-in-a-bottle moment that Shyamalan chased for as long as he could until the well dried up on The Village and his ego subsumed him with Lady in the Water, after which he wandered in the attempted-blockbuster wilderness for a while before settling into his current mode of making feature-length Twilight Zone episodes devoid of any satirical dimension or social commentary.
Coming out of the 90s, an era marked by economic stability and prosperity, a time in which things were as good as they were going to get for a certain type of upwardly-mobile white American, which was the exact demographic that had an absolute stranglehold on the culture. That’s how we have to define the “we” of mainstream society at this point, and as such “we” didn’t really have anything particularly interesting to say. The great movies were coming not from the studios but from the weirdos and outcasts, the new generation, and the marginalized.
We were also at this point in a mildly reactionary awards era, I’d argue - three years previous the slate is noticeably absent of big-studio fare, with a Best Picture field full of independent productions save for Jerry Maguire. Hollywood roars back the next year with Titanic, but they almost can’t claim it because of Hurricane Cameron (rightfully) swallowing up all of the credit - especially since he had to fight the studio tooth and nail to get it made. The 1998 trophy is seen as a stolen award, Harvey Weinstein flexing his muscle to get Shakespeare in Love the Oscar over Spielberg’s Saving Private Ryan (a decision I actually kind of defend despite Weinstein’s shady tactics and overall standing as a monstrous piece of absolute shit). By 1999 the studios have decided to have it both ways - swallow up the indies and do it themselves, so that they have “edgy” projects with big money backing. It can’t be understated how much the American Beauty win is a very conscious effort on the part of Dreamworks to win their Best Picture Oscar by any means necessary after the previous year’s “slighting,” though they hardly had to twist anybody’s arm seeing as Beauty was pretty universally heralded by critics and even audiences.
It’s a weird awards year that only obliquely recognizes what’s going on. Maybe y2k actually happened and we’ve either been dead ever since or slipped into the matrix. It would explain a lot.
Missing in Action: Eyes Wide Shut, The Matrix, The Straight Story, Topsy-Turvey, Magnolia, and Being John Malkovich are not just among the very best films of the year, but are also among the best films - if not the best films - for each of their respective directors, all of whom either are by this point or will soon be legendary in their field.
Best Director
This category takes a step in the right direction by swapping out Frank Darabont (The Green Mile) for Spike Jonze, whose Being John Malkovich is a startlingly original film that introduces two major cinematic talents to the world. We used to get these lone director noms most every year; who it came at the expense of varied, but the person who got in was usually someone who’s film was a little too daring or unique to make a Best Picture field of five, as was certainly the case here. The rest of the nominees are the helmers of the remaining Best Pictures. Mendes of course wins with little to no suspense.
Missing in Action: Stanley Kubrick, with Eyes Wide Shut, made a final film as touching as it is unsettling; Lana and Lilly Wachowski perfectly fused pop philosophy, anime stylistics, and Hong Kong action while also making a film that felt genuinely new in The Matrix; David Lynch took a story about an old man driving across the country on a lawnmower - and not doing all that much else - and made the most emotionally satisfying film of his career; Daniel Myrick and Eduardo Sanchez not only utilized a documentary aesthetic for a fiction film - something that had been done before by this point - with The Blair Witch Project, but the experimental means they used to develop the on-camera narrative and elicit genuinely terrified performances from their cast feels like a genuinely new and invigorating approach to cinema narrative; Paul Thomas Anderson’s Magnolia is a fairly towering achievement in epic emotionality, and the last film this ostentatiously stylistic and audacious that he would make (as of now); Martin Scorsese made one of his most underrated films this year in Bringing Out the Dead, a movie somewhat overdue the retrospective reclamation that some of his 80s pictures have finally been getting of late.
Best Original Screenplay

American Beauty
Being John Malkovich
Magnolia
The Sixth Sense
Topsy-Turvy
Is this the beginning of Best Original Screenplay being the haven of the movies too cool to have a shot of winning the big one? American Beauty wins, but the other four options are a much more representative line-up for the overall quality and importance of this year.
Should be Here: Bowfinger is one of the funniest movies ever made; The Matrix deserves inclusion for all the reasons listed above; Three Kings is not only an absurdly comedic tour-de-force, but is also one of the first major instances of a filmmaker questioning America’s military pre-occupation with Iraq; All About My Mother, while fantastic, isn’t even one of my favorite Almodóvar’s, but I just feel like he should always be here; Dogma may be a controversial choice but I still defend this script as a very funny execution of a fairly brilliant and thought-provoking conceit, even if it doesn’t quite go all the way there.
Best Adapted Screenplay
The Cider House Rules
Election
The Green Mile
The Insider
The Talented Mr. Ripley
Even this category, despite the presence of Rules and The Green Mile, digs deeper with Election and Ripley. Though again, the least interesting option wins in Cider House.
Missing in Action: With Eyes Wide Shut, Kubrick and Frederic Raphael brilliantly transposes the original novella from fin de siècle Vienna to modern-day New York while retaining its themes of sexual insecurity and class resentment; Paul Schrader turns Bringing Out the Dead even in all its frenzied, hallucinatory mania into a sort of spiritually-uplifting, positive inverse of Taxi Driver; John Roach and Mary Sweeney turn a premise that sounds like a joke into a story that is emotionally gripping and incredibly resonant with The Straight Story.
Acting
The performance categories are kind of their own beast because of the factors individual to an actor’s career that go into them, but let’s look at some specific bullet points:
Richard Farnsworth gets the sort of late-career nomination that can often come across as a retrospective bravo for years of consistent and strong work, but he may also be the most deserving winner here, and for a movie that’s better than most of what’s nominated. He’s one of only three acting nominations ever received for a David Lynch film (John Hurt for The Elephant Man and Dianne Ladd for Wild at Heart, the latter being one that she had to really fight for), and the last given that Naomi Watts would be criminally ignored for the best performance of the aughts (all time?) a mere two years later.
Kevin Spacey for American Beauty specifically has to be in the top 5 of awards they wish they could take back, right?
Supporting Actor has one of the strongest-ever lineups for a category that is always one of the stronger. It goes, of course, to the most sentimental and uninspiring choice.
Angelina Jolie is actually one of the few nominees, let alone winners, from this year that I still haven’t seen. This is a very strong category though, with Catherine Keener the critical favorite for Being John Malkovich while Toni Colette, as the constantly-frazzled parent constantly spiraling towards full-on nervous breakdown as she tries so desperately to do right by her precocious child while also having to work and maintain a life all without being able to ask anybody for help is probably my favorite of the bunch (can’t imagine why!).
Hilary Swank’s win is certainly one that may be a little fraught today as she is a cis woman winning for playing a trans man. I remember it as a phenomenal performance, but how much of that is based on problematic ideas of what constitutes bravery or a performer stretching themselves? I haven’t seen the movie since it was in theaters so I can’t speak to how well any of it is handled through a modern lens, though like The Insider it is certainly one that is sadly even more relevant today. I would be curious to know more about the trans perspective on this one.
I find it fascinating, as a side note, to watch her acceptance speech and notice that Roberto Begnini stands silently and respectfully behind her the whole time because it shows the degree to which his whole thing was just an act (moments earlier he was running around the stage with host Billy Crystal, who was chasing him with a comedically overlarge butterfly net).
General Impressions
Some additional observations on the rest of the field:
Topsy-Turvy’s strong showing is just an absolute delight. This was my first Mike Leigh movie - I was dragged to it by a friend who was much more of a theatre person than me at the time, knowing just that it was one of the “big players” this year critically and awards-wise. I was blown away by how much I loved it.
Pedro Almódovar takes the Oscar stage for the first time to accept the award for Foreign Language Film (the statue itself goes not to him but to the country of Spain); he’ll return to claim his own trophy in a few years for his Talk to Her script.
Eyes Wide Shut may be the best movie of this year - you could even make the case for the whole decade - and along with The Matrix seems to be, from my own anecdotal evidence, the one most resonant with younger generations today. It’s nowhere to be seen.
The Matrix sweeping the tech categories feels like the most correct thing about this whole awards year. It’s perhaps the nominated film that most represents the historical essence of this year and is a pretty keen example of the Oscars recognizing something revolutionary in the moment. I once know someone who was so angry that it stomped all over Star Wars: Episode I in all of its tech categories; can you imagine how embarrassed we would have been had those wins been flipped?
The Blair Witch Project, also release this year, may be even more influential than The Matrix even if its tail as a film doesn’t stretch as long. Beyond just a gimmick
The Broadcast

The show itself is in its own way sealed in amber. Peter Coyote, who I only recently learned lived on a commune for a few years before playing Keys in E.T. and chose that last name for himself after a peyote trip, opens the show and serves as the on-camera announcer (with a cameo assist from an unidentified hand - perhaps Academy president Robert Rehme, who is about to step on stage and introduce the evening and explain how the votes are tabulated). The large video screens on the stage scream that specific late-1990s/early-2000s liminal era, and rather than an orchestra they just have Don Was in the pit mixing classic movie themes with percussive club beats. My favorite example of this is probably Dame Judi Dench strolling to the stage accompanied by a re-working of the Shakespeare in Love theme complete with dub drums and record scratches.
The Oscars are somewhat synonymous with a certain degree of tacky kitsch masquerading as glamour. There’s a stark incongruity to this year’s show on an aesthetic level that befits a ceremony in which they are here and there attempting to honor the new guard while so often retreating back to what makes them feel safe and comfortable - sometimes within the same film.
-cs