If you've been here a while, you know the drill, but if you don't, we just finished up the 1999 OVP, our 26th season of the series where I go through and pick, after having seen all of the nominees, whom I would've chosen (in a vacuum) for all of the nominees that Oscar put in his narrative, feature-length categories. But we always end with an epilogue, where I turn the tables a bit and assemble my own nominees from scratch. This required, for 1999, a lot of heavy lifting. I was 15 in 1999, so while I did see a lot of movies (I have always been a big fan of going to the theater), most of these are ones that I have assembled in the years since as my parents were quite strict about watching R-rated movies when I was growing up. Case-in-point, only three of the Best Picture nominees were ones I saw in the calendar year of 1999 (and beyond that, only two of them were ones I saw in theaters-the romantic comedy nominee was a frequently screened VHS that my mom bought). I made a concerted effort to see a bunch of new movies for this that filled in gaps, though I'll own that not a lot of them stuck (only two of the below pictures were ones that I saw as part of my "catch-up" efforts, and none of them were ones in the Big 6), but if there's a movie that's not listed and also wasn't on Oscar's lists, don't assume I'm snubbing it before asking in the comments, as I'm only one man-I can't see all of the movies. Of the many I did see from the year, though, these are my favorites-enjoy and share yours in the comments (and if you want to see past my ballots or all of the other races in 1999, links are at the bottom of the article!).
American Beauty
The Blair Witch Project
East/West
Election
Eyes Wide Shut
Notting Hill
South Park: Bigger, Longer, and Uncut
The Sixth Sense
The Talented Mr. Ripley
Toy Story 2
Gold: Derided by some in its time, The Blair Witch Project is the movie that stands apart here primarily because it's a horror film that is truly effective at showing the worst in humanity, unfolding in seemingly real time. Bold, experimental, but always grounded in the fact that the scariest things are the things we don't see, it is one of the boldest experiences I've had watching a movie...and that ending...
Silver: Sequels rarely live up to their predecessors, but for Woody & Buzz, that's never been the case with their franchise. Toy Story 2 expands upon the initial concept to give us a look at how other toys will deal with being forgotten, and how friendship comes from whom you surround yourself with, not what you are called into being.
Bronze: A quick reminder that this is my favorite films list, not just what I'd pick in the lens of Oscar. So putting a film like Notting Hill, which has been one of my favorite movies for as long as I can recall into this spot is partially reliant on a childhood watching it every month. But Julia Roberts' heartbreaking self-examination and the really genuine look at romance as an obstacle mean this is not just a favorite film...it's a great one.
Stanley Kubrick, Eyes Wide Shut
Sam Mendes, American Beauty
Alexander Payne, Election
Eduardo Sanchez & Daniel Myrick, The Blair Witch Project
M. Night Shyamalan, The Sixth Sense
Gold: M. Night Shyamalan has gone from something of a pop culture punching to being a respected (though not revered) crafter of mid-level thrillers in the decades that followed him becoming a household name. But it's hard to argue with his initial breakout project, a spellbinding, perfectly-crafted thriller that looks at the heartbreak of grief & loss through the lens of a horror film.
Silver: Stanley Kubrick (one of my all-time favorites) has entered the chat on our My Ballots (this is the first time we've had a year where he was eligible), and he is doing so with a mysterious, oftentimes incomplete (in a good way) tale that provides us a look into the world of a man haunted by his own insecurities.
Bronze: Speaking of male insecurity, we have American Beauty, Sam Mendes' ambitious debut, which decided to mainstream a relatively new idea at the time-what evils were lurking within the hearts of the perfect, pristine suburbs. Mendes indulgence with the camera (giving us genuine risk that pays off in terms of sexuality, earnestness, & suspended belief) is an absolute marvel.
Russell Crowe, The Insider
Matt Damon, The Talented Mr. Ripley
Haley Joel Osment, The Sixth Sense
Brad Pitt, Fight Club
Kevin Spacey, American Beauty
Gold: You can quibble over whether I'm being too precious by putting Osment in lead or not (I do think this spot makes more sense), but honestly-he wins the gold medal either way. The way that he just owns the screen, his quivering voice & understanding of everything that's happening even before the audience does is something actors decades older than him would struggle to master.
Silver: Behind him is Matt Damon, giving the best performance of his career as the vain-yet-insecure Tom Ripley, a sociopath obsessed with becoming (and consuming) his ideal. The way that Damon uses his sexuality while also turning his star persona on its head is a fascinating chapter in a career of an actor who is not known for stretching himself, and it pays off.
Bronze: Listen, we are only listing actors here based on their performances, not their personal lives. And if we look solely at performance, it's hard not to consider Kevin Spacey's father-on-the-brink, having a midlife crisis that tears down so many (including himself) around him as one of the defining Oscar-winning performances of the 1990's.
Annette Bening, American Beauty
Julia Roberts, Notting Hill
Cecilia Roth, All About My Mother
Hilary Swank, Boys Don't Cry
Reese Witherspoon, Election
Gold: Reese Witherspoon is one of those actresses who has made a lot of really forgettable pictures (frequently in the name of solidifying her crown as one of the final rom-com queens before that era ended), but when she's on her game, she's just beyond, and that's the case here, where she becomes our second performer (after Nicole Kidman, whom we're going to get to in a second) to win three gold medals for Best Actress as the unbeatable, insufferable, unrelenting Tracy Flick.
Silver: This means we might never see Julia Roberts clutch a gold medal in this project, and while I do this in a silo (you gotta vote for the best, and in this case that's Reese), that's a darn shame. After all, what Roberts is doing in Notting Hill is really special-giving us a lived-in look at a real life sketch of herself, the beautiful-but-bruised movie star.
Bronze: With a far more realistic portrait, our final Best Actress medalist is Hilary Swank, the one who would win the Oscar in 1999. Her Brandon Teena is so real-this is a bleak movie, but look at the way that Swank in habits Brandon's joy, their hope, which makes the crushing reality of prejudice feel all the more disappointing when it rears its inevitable head.
Michael Caine, The Cider House Rules
Tom Cruise, Magnolia
Jude Law, The Talented Mr. Ripley
Christopher Plummer, The Insider
Hugo Weaving, The Matrix
Gold: Tom Cruise would never quite challenge himself in future roles as much as he did in Magnolia (his last acting Oscar nomination to date), but man was this an exit. Playing a version of himself, and perhaps more crucially, a version of his idol L. Ron Hubbard (something it's still not clear Cruise knew he was doing), he embodies a type of toxic masculinity for profit that would become the dominating force in American conservative culture for the next several decades.
Silver: Jude Law's face and body are, admittedly, part of what makes Dickie Greenleaf work. God gave him those gifts, but they're essential to the picture. What Law brings, though, is the confidence and callousness that comes with being so desirable that no one around you ever makes you face consequences, and the maddening danger that happens when that world shows its cracks.
Bronze: Christopher Plummer's work as Mike Wallace is maybe the best of his career? It's certainly the most actorly, giving us a "man of truth" that is also vain, entitled, and ambitious without entirely feeling ruthless about it (even if it's a driving force). I love when we see the facade fade without it feeling expositional...it's just full of character detail that makes you understand this reporter.
Cate Blanchett, The Talented Mr. Ripley
Toni Collette, The Sixth Sense
Catherine Keener, Being John Malkovich
Nicole Kidman, Eyes Wide Shut
Julianne Moore, Magnolia
Gold: Toni Collette's hands do so much work in The Sixth Sense. It's the first thing you think of, her flawlessly manicured nails and the way she doesn't want to get them messed up as she's crying in her car. This is the sort of specific character work we've long expected from one of the most underused actresses of this century, totally acing the part of a woman understanding her son (while also feeling broken in her own skin).
Silver: Julianne Moore gives us the quintessential bitchy trophy wife, trying to come to terms with the fact that she fell in love with a man for his money (but eventually fell for him). Struggling with drug issues, complicated emotions, & depression, we get Moore at her best here, a woman on the brink (and with some of her best onscreen crying, which for Julianne Moore is saying something).
Bronze: Like I said above, we were going to return to Nicole Kidman. Kidman was about to enter her auteur era (though if you look at her filmography, that's honestly her entire career), and she did it with aplomb opposite Stanley Kubrick in this spin on the bored, horny housewife, giving us not just a spin on this movie staple, but also on the movie star super-couple (giving us titillating insight into her soon-to-collapse marriage to Tom Cruise).
Election
Eyes Wide Shut
The Insider
South Park: Bigger, Longer, and Uncut
Toy Story 2
Gold: I've said it before-Alexander Payne is not my cup-of-tea, and other than Sideways, Election is the only film of his that I really clicked with...but you don't lose points for the rest of your filmography. This is an A+ effort, the best screenplay of 1999, filled with quotable lines, genuinely shocking twists, and some of the best use of narration to guide the story I've seen in a movie.
Silver: I'm still not entirely sure how I feel about listing all sequels as adapted, but we're just going to go with it here, as Toy Story 2 is too good to deny. The way that it quickly builds off of the original while also giving us a unique spin on a story we've already seen (a toy rejected by an aging child), is marvelous. Plus, the introduction of key characters (like Stinky Pete & Barbie) are done perfectly.
Bronze: Michael Mann's The Insider is a really well-constructed thriller, giving us a story most already knew at the time, but filled with twists and insights that make you desperate to know what happens next. The dialogue is also really strong, particularly the work around Plummer's Mike Wallace, giving us the commercial side of being a "respected journalist."
American Beauty
Dogma
Notting Hill
Ratcatcher
The Sixth Sense
Gold: "Do you know why you're afraid when you're alone?" "I see dead people" "Do I make her proud?" Horror movies are frequently filled with cheesy lines, but The Sixth Sense turns that on its head with an earnestness that gives the screenplay not just scares, but also a lot of empathy & understanding, critically important as we move through the picture.
Silver: Alan Ball's slice-of-suburbia in American Beauty is so borrowed-from, you might watch it today and assume it's just cliche and not the prototype to decades of family dysfunction. Kudos in particular to the way he handles the decay in the marriage without the main actors spending that much time together-you see them growing apart separately, something you don't oftentimes get (but is reflexive of reality).
Bronze: Comedy never gets its due from the Oscars, particularly for the writing categories where it most earns it. Think of the dinner party scene, which alternates between genuinely funny bits ("$15 million...right, well that's fairly good") to heartbreaking ("I'll look like someone who was famous for a while") all in single leaps. Notting Hill has that level of care in its writing.
The Iron Giant
South Park: Bigger, Longer, and Uncut
Toy Story 2
Gold: For much of the 1990's, the concept of a Disney animated sequel was that they were disposable, stuff that you'd shove onto a VHS tape and sell to hapless parents who were stuck shoveling out cash for mediocre ripoffs. Then Pixar made Toy Story 2, and it was marvelous-a movie that genuinely lived up to the original, changing the trajectory of both studios forever.
Silver: The antithesis of Disney, South Park didn't wait like The Simpsons or Bob's Burgers to get its movie out after a decade of goodwill. Instead they were ready for a masterpiece right away, giving us a tale of Satan vs. Canada, a spoof on the 1990's obsession with puritanical virtues at the movies.
Bronze: Relatively straight-forward animation masks that The Iron Giant is a really wonderfully-executed story. The pacifist vision combined with the B-movie 1950's space film aesthetic works really well, and gives us a beautifully-executed finale.
The Blair Witch Project
The Matrix
The Sixth Sense
Star Wars: Episode 1 - The Phantom Menace
Toy Story 2
Gold: One of the things I love about the sound mixing in the The Matrix is the way it so aides the story. Think of the way that we understand the sewer system, or the thundering roar of the score, in the picture. There are movies where this can feel lazy, but for The Matrix it's building an entire world onto itself-it needs to have these sorts of cues for the audience to follow along, and it works beautifully in its translation.
Silver: Case in point, you have something like The Phantom Menace, the first of (to date) eight Star Wars follow-ups that have borrowed from the sound work of the original trilogy, and here it's really well-done. Much of Phantom is animated (or uses puppetry depending on which Yoda you're watching), so it needs to match up precisely, making you truly believe that Jar Jar Binks is standing right next to Natalie Portman.
Bronze: The Sixth Sense uses its own spooky score to its advantage, frequently accentuating the bumps in the night onscreen. But the dialogue ultimately gets you the medal, the way it feels frozen in the moments of the screen, Osment's pin-drop confession or Toni Collette's stifled plea for her mother's love one last time.
Fight Club
The Iron Giant
The Matrix
The Mummy
Star Wars: Episode 1 - The Phantom Menace
Gold: The Matrix-think of what you first think of when you remember the movie. Is it the falling data popping green code onto your television set? Is it Keanu Reeves flying through the air with a giant whoosh across your big movie screen? Is it the sound of rain & water plinking through the sewers from your iPad? No matter how you watch the picture, it's really the sound editors making you get into this world.
Silver: The Phantom Menace lives-and-dies off of of its sound editing. Think of a scene like "activate the droids" where you have specific preparations for battle, robots clinking and shields going up, but each make-and-model has its own, unique sound. This attention to detail is why the Star Wars franchise is basically better at this than anybody.
Bronze: Fight Club doesn't have the advantage of creating a world from scratch, but what it does do is what all great David Fincher movies do-craft an impeccable background to the picture through sound. Recall the moment where Edward Norton is shooting Brad Pitt, and the bullet goes not just through the back of the van, but the front. The audience doesn't just get the heightened sense of danger...they also get every crackle of glass and metal against each other, making it a truly visceral experience.
American Beauty
The Cider House Rules
The Mummy
Star Wars: Episode 1 - The Phantom Menace
The Talented Mr. Ripley
Gold: Rachel Portman followed up her Oscar-winning work in Emma with another Oscar citation for The Cider House Rules. Much of the reason that this film works lies in Portman's score-giving us soaring interludes (and incredibly memorable music-there's a reason this shows up in trailers) to go along with the changing of the story. This isn't bold, but it's classically-done and, in my opinion, pretty flawlessly-done orchestral music perfect for the film. I love it.
Silver: Percussion is the key to American Beauty's distinctive tones. We have xylophone, drums, and marimba pushing through to give us modernist notes (something that Thomas Newman, admittedly, would bring to a lot of his work with less success in the years that followed), and made a score so beloved it would play on local radios in LA at the time. Had Newman won the Oscar for this (to date, he has yet to win one), it would've been a win that aged well.
Bronze: Gabriel Yared is the only one of these five nominees that is trying to match his score to a very song-heavy film, which can be tricky. But I love that Talented Mr. Ripley doesn't shy away from that, with music coming from every angle of the picture, whether it's Charlie Parker & Miles Davis, or Yared putting in an enigmatic, tricky sound to keep the viewer guessing.
"Blame Canada," South Park: Bigger, Longer, and Uncut
"La Resistance," South Park: Bigger, Longer, and Uncut
"Save Me," Magnolia
"When She Loved Me," Toy Story 2
"The World is Not Enough," The World is Not Enough
Gold: The music of Aimee Mann in Magnolia is on another level. The best scene in the movie is probably "Wise Up," which was not an original song, but is best-employed. But if you want the best overall song (and one of my favorite songs, period), you need to go with "Save Me," an ode to wanting to be rescued even if you don't know where the life raft is coming from.
Silver: A true-and-proper musical, every song in South Park is a strong effort-Matt Stone & Trey Parker had the good sense to hire Marc Shaiman (a proper musician) to lead their cause. The best song in the film, thanks in large part to Shaiman's respect for musical theater, is the Les Miserables parody "La Resistance," funnyily blending together previous tunes, and coming up with a totally South Park level of crazy.
Bronze: Randy Newman's best movie song? I think it'd be hard to argue when you're listening to "When She Loved Me," sang with an incredible amount of heart by Sarah McLachlan, as we get a sense of why Jessie needed to be found by Woody & Buzz, and the sadness that comes from leaving your childhood behind.
All About My Mother
Eyes Wide Shut
Sleepy Hollow
Topsy-Turvy
Toy Story 2
Gold: Possibly the best-looking film that Tim Burton has made, Sleepy Hollow takes a century-old style and gives it his own spin (without sacrificing the illustrations we've grown up with in storybooks reading this tale). A true gothic horror town, expanding its settings even into the twisted trees of the natural world alongside the staged village within.
Silver: Animated films do not get enough love outside of the music categories for my taste, and a good example as to when they should be included is Toy Story 2. Think of how crucial art direction is to this film-the entire concept of the toy store, empty but filled with life (the Barbie world, Rudy's round-up collection) once the toys are let to play. It's great stuff.
Bronze: The heightened beauty of Pedro Almodovar's films is easiest to see in All About My Mother. Using consistent color palettes (lots of red & yellow), you feel like you've fallen into one of the movies that Pedro watched as a child, filled with melodrama and the little touches of film noir in each exquisite set design.
All About My Mother
American Beauty
Eyes Wide Shut
Sleepy Hollow
Snow Falling on Cedars
Gold: In my opinion the finest work of Robert Richardson's career, Snow Falling on Cedars is a painting. Moody cinematography is the hallmark, particularly when you look at scenes shot at night (think of the light-in-nighttime here and shudder at what would come in the new century), with Youki Kudoh and Ethan Hawke both looking ravishing at every turn.
Silver: The art direction & cinematography of All About My Mother go hand-in-hand, and not just in the themes. Ross Hunter & Fritz Lang it feels like in equal measure are being recognized in the switches between set-engrossing wide shots and quick, emotive close-ups of the actresses on the screen in front of us.
Bronze: Color is a big part of the story of American Beauty, using the camera to unfold layers. There's the obvious (and famous) outpouring of rose petals from Mena Suvari's cheerleader uniform, giving us a sense of falling (which is what Lester is about to do), but that's throughout-the rain, the floating bag, the camera is Sam Mendes' right-hand man when it comes to giving us the sense of anguished whimsy at the core of this picture.
The Matrix
Sleepy Hollow
The Talented Mr. Ripley
Tea with Mussolini
Topsy-Turvy
Gold: Like I said above, Sleepy Hollow is maybe my favorite of all of Tim Burton's films based solely on what we're seeing onscreen aesthetically. My favorite dress in the film is the one worn by Christina Ricci, black-and-white striped with a collar that makes it feel like she's trying to hypnotize Johnny Depp (and the audience). Throw in a bunch of lusty looks from Miranda Richardson, and you've got yourself a picture.
Silver: Duster jackets abound in The Matrix, but this is only part of the story. The switches between characters, frequently trading on similar looks. Examine the way that Keanu Reeves, Laurence Fishburne, & Carrie-Anne Moss all wear the same palette, to indicate uniformity, but thanks to designs look totally difference, almost tricking the audience (which is the point of the Matrix).
Bronze: There's always at least one nominee here that is getting their citation because of the looks it gives male actors, and that's true of Talented Mr. Ripley. While Ms. Paltrow & Ms. Blanchett are wearing fine frocks, I'm most obsessed with Jude Law's grey vertical striped shirt (so effortless...so impossible for virtually anyone else to wear without looking boxy) or Matt Damon's neon yellow swimsuit to prove he's ready to stand out. It's all scrumptious.
The Blair Witch Project
Fight Club
The Insider
The Matrix
The Sixth Sense
Gold: Hey Oscar-we actually agreed on this one (we're both picking films not nominated for Best Picture as our Editing gold medalist, for me only the second time after 2015's Embrace of the Serpent that this has happened and something just as rare for AMPAS). The winner is The Matrix, a textbook example of how you can use repetition, expositional storytelling, & a visual language to tell a story.
Silver: The Sixth Sense is infamous for its twist ending, which only makes sense if it's telegraphed but you don't know that it's coming, and of course that's done perfectly here. But the silver medal isn't just from that-it's also the way the team makes Osment's character a vessel, guiding people to their fates, and to some sense of closure...without giving away the ending.
Bronze: 1999 is filled with films that inspired a lot of copycat work in the years that followed. Fight Club is one of the best examples of that, another movie with a twist ending who uses a frenetic pacing and sense of masculinity in its cutting room to give us a tricky, difficult story. David Fincher remains unmatched in giving us that kind of sophistication in his film team.
Fight Club
The Insider
Sleepy Hollow
Star Wars: Episode 1 - The Phantom Menace
Topsy-Turvy
Gold: For me, it's the realism in Topsy-Turvy that makes it the gold medalist here. The teeth and aging work are something-authentic but never feeling like they're over-the-top or calling attention to themselves. I'll own that there is some use of yellowface, but it falls under the banner of Tropic Thunder (it's historically accurate & worn by characters as a plot point, rather than just as a trope), but if you can move past that, you have an obvious winner for makeup.
Silver: I love a movie that uses makeup as a plot point, and that's clearly what Fight Club is telegraphing here. Look at the way that Edward Norton is perpetually exhausted with the bags under his eyes, or how Helena Bonham Carter's heavy eye shadow hides her true emotions, or how the blood on Brad Pitt's face still seems somehow impossibly sexy. This is all character development made in the makeup chair.
Bronze: The makeup in Sleepy Hollow unfolds with alabaster looks from virtually everyone. Even gorgeous actors like Johnny Depp & Christina Ricci feel period-appropriate (recall her pancake makeup against the blonde locks, or the way that Johnny Depp's hair looks impossibly coiffed, as if he's stuck mid-pose in many scenes). Add in Christopher Walken's sharpened teeth and gorgon blue eyes as the Horseman, and you're in for a treat.
The Haunting
The Matrix
The Mummy
Sleepy Hollow
Star Wars: Episode 1 -The Phantom Menace
Gold: Somehow the first gold medal I've given the entire Star Wars franchise (we haven't done the original trilogy which will surely change this stat, but after 20 nominations, which won 7 silver's and 4 bronze's, this is the first time it's taken a gold). This feels right though-Phantom Menace is gigantic, epic storytelling and would usher in a new wave of computer effects to the big-screen, and it looks incredible.
Silver: More stylish, but with slightly less marvel, is The Matrix, coming close behind. I love the use of stunt coordination here with the special effects, giving us a lot of borrowing from the filmography of John Woo. Combined with the use of color in the CGI (green becomes a dominant force in a movie where you can be red or blue pilled), it knows how to build and use effects on a budget.
Bronze: Our final medalist of 1999 is The Mummy, which feels fitting as I always lump these three together. While Star Wars was breaking new ground and The Matrix was setting up decades of imitators, it's The Mummy that plays with classic motifs the best, giving us a gigantic, gaping hole in the desert and startling makeup & visual effects as we traverse familiar horror movie territory as if for the first time.
Also in 1999: Picture, Director, Actress, Actor, Supporting Actress, Supporting Actor, Adapted Screenplay, Original Screenplay, Foreign Language Film, Sound Mixing, Sound Editing, Original Score, Original Song, Art Direction, Cinematography, Costume, Film Editing, Visual Effects, Makeup, Previously, in 1999
