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The Best Oscar Winning Original Screenplays of the 2000s, Ranked

By Preston Garrett · August 19, 2010

Let's be honest – there have been some major hits and misses at the Oscars, and the Best Original Screenplay award is no exception.  Since the category originated in 1940, there have been some major head scratchers that have left many a filmgoer aghast, annoyed, disappointed, and above all, worried about the integrity of the Academy.

With that said, for the next few weeks I'm going to delve into the category of Best Original Screenplay winners over the decades past, starting with the freshly finished 2000s, working backwards.  
I've ranked this list by what I feel are the most deserving of the Best Original Screenplay Oscar, to the least deserving, and have provided, in many cases, a fellow nominee or nominees of the same year that I feel should have taken home the statuette that's supposed to be the end all/be all of film awards.
Without further ado, the worst to best Best Original Screenplay Oscar winners of the 2000s.

10. Crash (2005)

Just under 5 years ago, when Crash's writers Paul Haggis and Bobby Moresco took home the gold for this ensemble, Altman-esque dissection of racial inequality in Los Angeles, a lot of critics were pissed off.  And I was one of them.  Though I don't think Crash is a particularly bad film, it's overall tone is trite, yet the intentions are good.  I totally appreciate anybody who wants to use film to encourage people to move past their prejudices.  But the thing with Crash, especially when thinking of the whole definition of "Oscar worthy," is that it's one of those films that's been done many times over, more effectively with better writing, structure, dialogue, plot and characters.  Going back to the "Altman-esque" statement, films like Nashville, Short Cuts, Magnolia and even American Graffiti are the films from which Haggis and Moresco blatantly steal to cliche effect.  Arguably, the subject matter is more poignant than the previous mentioned films, but what all these films boil down to are the capturing of slices of life within a single day of many intersecting peoples' lives.  Though they "steal" from each other in a way, the writing of these films is to such a superb level that their similarities in structure are negligible at best – they each have their very own voices.  Crash simply lacks that individualism.  What should have won: The Squid and the Whale – written by Noah Baumbach.

9. Juno (2007)

Many people love this film, and for good reason.  It's witty, charming, and chock full of pop culture references – kind of like an episode of a VH1 countdown.  It makes you feel comfortable when you stay at home sick, or it's something you can just turn on and tune out while you're fiddling around the house.  I personally love movies like these (The Goonies happens to be my mainstay.)  But when it comes to being Oscar worthy, Diablo Cody's tale of teen pregnancy, off beat-ness, hipsterdom, and ridiculously sweet toothed dialogue simply doesn't get past it's charm.  I actually find it's overwhelming, almost annoying charm to be it's main downfall.  I like to imagine what this film would have been like if it had toned down the comedy and giant winks at the audience, and had instead taken itself a little more seriously.  Maybe it would have fallen flat, and maybe Cody's "charm" is what ultimately coaxed the Academy into giving away the award, but I simply think charm gets you only so far.  Kind of like when you're on a date – if you're charming but you don't pay, say something genuine, or make an effort to say something with a real inflection, you'll go home alone.  Cody flirted with her audience – she never kissed them goodnight.  To boot, it just kind of makes me wonder how the Academy never gave an Oscar to John Hughes, a writer whose personality and charm actually took itself seriously in many of his films.  I mean, The Breakfast Club, Planes, Trains & Automobiles, and even Ferris Bueller's Day Off – seriously.  What should have won: Michael Clayton, by Tony Gilroy.

8. Gosford Park (2001)
There really isn't anything wrong with Gosford Park.  Julian Fellows' dinner theatre whodunit is a masterful noir construction.  What's so great about too is that the noir protagonist is a female (Emily Watson).  The ensemble cast is superb, the dialogue is totally witty, and though on the surface it looks as if it could be stuffier than a hypochondriac's nose during cold and flu season, Gosford Park has a very distinct, ever-changing personality throughout.  It shifts from silly to dark, romantic to dreadful, endearing to cold.  So why is it so low on the list?  This is one of the few cases on the list where the competition was simply that much better – Memento was up for the Oscar the same year.  I almost feel like that's all I have to say… but I'll continue.  One reason Christopher and Jonathan Nolan's script apparently didn't get the ultimate awards props was because they weren't in the WGA when awards submissions took place.  Thus, the Academy felt political pressure to honor the Union-ites that have an On the Waterfront pull in Hollywoodland.  If you don't recall the release of Memento, I'll refresh your memory.  It was one of maybe 3 films that have come out in my lifetime that has transcended all demographics of people as being hailed "excellent."   I'm wary of going further about this in case you haven't seen Memento, but this backwards tale of revenge and amnesia is the crime thriller Fellini would have made.  That and maybe Inception.  What should have won: Memento.

7. The Hurt Locker (2009)
The last Original Screenplay and Best Picture winner of the decade couldn't have been more topical for the a 10 year span of economy driven war, fear, and paranoia.  Mark Boal's narrative, which almost feels plotless in the traditional sense, is a frenetic 30+ day POV experience within the confines of US bomb squad unit – a story like nary told other than maybe Blown Away (look it up.)  The Hurt Locker kicked me in the stomach when I first saw it, catching me off guard – I had expected action more than anything else, not an intimate exploration of emotion.  Yet, being surprised by how a film makes you feel doesn't necessarily dictate it's overall excellence.  While The Hurt Locker is certainly an incredible film, the simple fact that many a US bomb squad veteran of the latest war in Iraq have refuted the authenticity of the film.  Obviously this largely falls on the shoulders of the screenwriter.  And though the film still stands alone as being moving and incredibly made, part of the experience is cheapened when you have that notion in the back of your mind that it's partially a crock.  What should have won: Inglourious Basterds, by Quentin Tarantino.

6. Milk (2008)
Dustin Lance Black's biopic script about the first openly gay, elected public official is harrowing, touching, and above all, so relevant to the bizarre and archaic sexual politics that we're still struggling to come to terms with as a nation today.  But to me, this film wasn't so much about great writing – this was much more a performance piece, driven by Sean Penn, Emile Hirsch, and Josh Brolin.  Yes, Black laid a taut framework for them, but excellent casting and directing by Gus Van Sant is what ultimately made this an excellent film.  This is something I find with biopics – they're hailed many times over as incredible writing achievements, yet they're almost entirely contingent on their performances.  Think of Ray, Walk the Line, and Nixon.  All were hailed as writing milestones at the time of their releases, but it's the performances of Jamie Foxx, Joaquin Phoenix, and Anthony Hopkins that people really and truly remember.  There's no seminal scene in these films that people necessarily cite as being incredible or innovative – it boils down to the presence and authenticity the actors brought to the table.  This isn't to say Milk is mediocre in spite of its performances – quite the contrary.  Yet pitted against other winners of the decade, this is where it falls on the list.  What should have won: give the year's other nominees, Milk certainly was deserving, but I'd be lying if I said I wasn't rooting for WALL-E by Andrew Stanton, Jim Reardon, and Pete Docter come Oscar time in 2009.

5. Little Miss Sunshine (2006)
Road trip movies.  They're something we'll never see go away, even if we we're traveling solely by spaceship in the next hundred years. There's something so intimate about the time you spend with people in the car for an extended period of time, especially with family, and especially if you can't stand your family. Michael Arndt captures this almost perfectly with Little Miss Sunshine.  Every time I see the opening credits sequence I almost burst into tears – that close up on Olive's giant, geriatric glasses with the reflection of the VHS taped beauty pageant bouncing back at you.  It's gorgeous because the movie itself is vulnerable.  Though at times Arndt's script becomes a little too frustrating, in an almost Meet the Parents sense – you just want someone to get a break.  I know this is part of the novelty of the film – there is no break until the whole dysfunctional family lets itself off the hook at the very end.  But some of their actions and caricatured personalities are a little too much.  I don't buy a teenage kid remaining mute for that long (I'm sure there have been… but eh.)  Or a dad being that narcissistic and delusional (again, I'm sure there have been.)  Alright, so maybe the movie is realistic, but there's a certain sweetness that permeates the film that just rubs me strangely.  Call me cynical, call me bleak, but this really all boils down to preference.  I really just feel there was more for Arndt to do to make this reality totally believable.  What that is exactly, I'm not really sure.  What should have won: Pan's Labyrinth, by Guillermo del Toro.

4. Lost in Translation (2003)
This film has been mentioned elsewhere on TSL's List circuit.  Sofia Coppola's offbeat, Harold and Maude-ish love story succeeds with its charm where Juno fell totally flat.  Coppola uses restraint – she leaves things to the imagination.  Who would have though a lack of dialogue altogether could say infinitely more than a page long soliloquy of Hipster drivel?  It's one of those rare films that is well liked by a wide audience in spite of ambiguity.  So much of what the characters feel is witnessed, not heard.  You can see the internal dialogue going through Bob and Charlotte's heads when their with each other.  Yes, this has a lot to do with acting, but if you take a look at Coppola's script, it's all on the page.  The light, almost accidental touch of hands; the grasping of the foot while lying on the bed; the mute, somber, and annoyed reaction of Bob when 2 yuppies recognize his celebrity.  The bottom line is that you believe and know Bob and Charlotte because we all have a little (or a lot) of Bob and Charlotte in all of us. They're flawed, but that's why we love them.  Harsh critics of Lost in Translation lambast it for this very quiet I'm hailing, but I really think this is just a sign of how ADD our society is becoming at large.  There are invisible explosions on the screen (and the page) that Michael Bay could never hold a squib to.  What should have won: Lost in Translation, though I would have been only slightly disappointed if Dirty Pretty Things by Steven Knight had dark horsed this one.

3. Almost Famous (2000)
Cameron Crowe's semi-autobiographical film about a teenager's love for rock and roll is simply one of the most enjoyable film experiences I've ever had.  Being a nerdy music lover almost as much as a film fanatic, Crowe's script is so good because it speaks to everyone.  It's a story of nostalgia.  It's a crying out for the power of youth.  It's a cynical look at the record industry.  And it's a love letter to the history of music.  Almost Famous is simply living and breathing proof of incredible storytelling. There's nothing very outside the box or unique about the plot.  Like Little Miss Sunshine, it's a road trip movie with many fantastic stops along the way.  If there's anything to hail Crowe for, more than anything, is his ability to construct complex characters that are equal parts despicable and lovable.  The character of William is one of the ultimate naive protagonists in film – we're exposed to the world of rock and roll with wide eyes every step of the way, and we're just as trusting and affectionate of the Stillwater mafia.  Above all, Almost Famous is a totem to "writing what you know," and exploiting a unique life experience that everyone can relate to in some shape or form.  Believe it or not we all have these – it's just a matter of figuring out the best way to let it live on the page.   What should have won: Almost Famous, though this was a great year for Originals – Billy Elliot by Lee Hall and You Can Count on Me by Kenneth Lonergan are on an equal par with Crowe's original eye.

2. Talk to Her (2002)
Pedro Almodovar is continually praised for his eclectic eye for the unusual, and making it a universal experience for his viewers.  He has no shortage of bizarre fare that continually get endless praise for their originality – Volver, Bad Education, and All About My Mother are no exceptions.  But Talk to Her is certainly Almodovar's seminal masterpiece.  For the category of Original Screenplay, it's hard to think of a more truly original story than this one.  The basics: a professional female dancer is in a coma for years; her deranged male nurse falls in love with her.  Flashbacks and surreal perspective of reality ensue as the nurse and another man both mourn for their loved one who are both in comas.  I know this sounds addled, somewhat disturbing, and almost too bizarre, but what Almodovar does better than almost anyone: he takes the awkward human condition – the dark parts of the soul that you can't stifle no matter how hard you try – and lets those flaws flourish.  You rarely feel ill will, resentment, or and sense of judging with Almodovar's characters in Talk to Her, in spite of their ridiculously selfish and strange nature.  You can't help but feel pity and a sense of your own self within each of them, whether it's their obsession, heartbreak, or greed.  I feel like this film is under viewed, so I'll spare major details.  But one thing I feel as to be mentioned, is the fact that Almodovar won an Academy Award almost solely because he successfully wrote a silent film sequence about a miniature man crawling inside a vagina, and his henceforth exploration of said vagina a la Caligari.  It's brilliant, strange, and beautiful.  What should have won: Talk to Her, yet this was another fantastic year, especially with Todd Haynes' Far from Heaven, and Alfonso and Carlos Cuaron's Y tu mama tambien.

1. Eternal Sunshine of the Spotless Mind (2004)
Anymore the love story is a formulaic genre, even when you see the comprehensive deconstruction of a relationship, as opposed to the long weekend, love at first sight Romeo and Juliet origins of romantic storytelling.  With films like When Harry Met Sally…, Annie Hall, and Love Story, real complexity was brought into the genre.  More than anything (as has been the theme with this entire list, especially the top tier of films), relatable characters whose flaws are both endearing and dastardly are what make these movies so incredible.  What Perre Bismuth, Michel Gondry, and Charlie Kaufman did with Eternal Sunshine of the Spotless Mind: they flipped the now cliched romantic deconstruction and flipped it on its head.  We don't see the impetus of the relationship to the end – we see the break up, and work backwards, tracing the complex arch of 2 lovers' resentment for one another, to their affection and slight frustration, to the honeymoon is over, but we're still in love phase, to the head over heels phase, all the way to the skittish initial attraction.  What makes Eternal Sunshine so fantastic and moving though, isn't the just the simple fact that we're moving backwards – it's the context.  Joel decides to get his memory of Clementine erased after he finds out she in fact got him erased from her own memory.  Manifest heartbreak.  I know I've talked about this film at length before, in particular the screenplay, so I'll keep it brief.  Yet the B storyline needs to be given props in a huge way.  The side love story of the Lacuna (mind erasure) workers' is the perfect, unexacting foil to Joel and Clementine's relationship, that spins around 180 degrees out of nowhere.  This script really is as close to perfect as films can get.  What should have won:  the Academy certainly did right by itself this year, though The Incredibles by Brad Bird certainly deserves and honorable mention, as well as John Logan's The Aviator, an incredibly underrated film.