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5. Donnie Darko (2001, dir. Richard Kelly)
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In the months and years following it would deservedly earn its cult status, yet it still feels somehow under-appreciated both as an ingenious genre bender and an angsty coming-of-age drama. At first, I didn't "get it," not realizing that full enjoyment of the experience has nothing to do with that at all. You could see the film as many times as you wish, immerse yourself in the details of the fictional "Philosophy of Time Travel" book, defer to the director's cut for more concrete answers (I've opted not to), but while the plot remains a brilliant, mulit-layered construct, it's actually the characters and performances that stay with you and demand revisiting. Donnie's relationship with Gretchen (Jena Malone) and the hypocrisy of the adults in the movie vividly brought to life by Beth Grant as the school's religious zealot and Patrick Swayze (in the edgiest role of his career) as motivational speaker Jim Cunningham. And of all the closing shots this decade, I have trouble coming up with anything more memorable than the one that ends this film. It's just perfect.
What's most shocking about Donnie Darko for me is that after a six year wait that was well worth it, Kelly would go on to write and direct a movie I believe is even better (see below). And although many would probably disagree with me on this next point, all the promise he showed in his debut feature would be fulfilled in the next two, creating a wholly original sci-fi trilogy and in the process making this film play even better in retrospect. It's just a shame even many of Darko's supporters don't see it that way, seemingly unaware of the risk-taking weirdness they signed up for nine years ago.
4. Southland Tales (2007, dir. Richard Kelly)
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There's more going on in a single scene in this movie than many contain in their entire running times, and no matter what you think of what's going on, it's tough to turn away. Yet, it breaks every rule in the book. There isn't a single character you can actually relate to as a human being. The person who should be the main character isn't. It's jammed with sub-plots that seem to go nowhere and everywhere at the same time. And it's filled with enough voice-over narration to fill an entirely separate film. And I don't even know how to explain away the cruel irony that my favorite scene of the decade is a musical number. The thrilling scene in question (Justin Timberlake's hallucinatory lip synch to The Killers' "All These Things That I've Done" surrounded by Marilyn Monroe looking women in scantily clad nurses uniforms) does little from a narrative perspective to advance the actual story in any way, yet somehow the film feels like it couldn't exist without out. The plot isn't complicated there's just A LOT going on and things are moving so fast and bursting with all this energy that at times it's tough to keep up. What's really required is an open mind and repeated viewings. Story-wise all the pieces fit together perfectly, it's the underlying meanings and symbolism that require extrapolation.
We're so used to actors being chosen on the basis of whether they "fit the part" but here the game completely changes as everyone is cast ironically. The parts seems to be tailored to who's playing them in an intentional attempt to go against type in a way that spoofs their celebrity and pushes them as actors to go places we never thought they would. Justin Timberlake as a Robert Frost-quoting scarred war veteran and Old Testament prophet. Dwayne "The Rock" Johnson as an amnesiac movie star with ties to the Republican Party who co-wrote a screenplay foretelling the end of the world. Mandy Moore as his wife. Sarah Michelle Gellar as a porn star and aspiring reality TV hostess. American Pie's Seann William Scott as, um, I can't even begin to describe it. Kelly's decision to basically throw a party on screen and invite all of his favorite actors and celebrities (a who's who of former Saturday Night Live players like Sheri O'Teri, Jon Lovitz, Norah Dunn, Amy Poehler and '80's cult favorites like Wallace Shawn, Zelda Rubenstein and Christopher Lambert) inexpicably drew really strong criticism. He wanted to give comic actors he's a fan of a chance to show audiences that they're capable of more, which they all did. It's just about the best reason there is to cast someone.
There are plenty of movies to return to repeatedly but this feels like a completely different one each time out. A dark political satire, A science fiction romp, a laugh-out-loud comedy, an action adventure, a social commentary, a film noir, a thriller, a musical and a mystery. I don't need ten films this decade when they're all in here. And each time it ends I just want to go back to the beginning and start all over again, hoping I'll understand everything, but knowing that I don't really want to. That's where most of the fun lies. It would be nice if eventually the movie gets the respect it deserves but that's inconsequential. Just that it was made and somehow released is proof that even the craziest ideas deserve a canvas for expression.
3. Almost Famous-Untitled: The Bootleg Cut (2000, dir. Cameron Crowe)
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It's difficult to find anyone who can't in some way relate to the protagonist or doesn't love the music. Or anyone who didn't feel as if they already knew (or desperately wanted to know) Penny the second she appeared on screen. We're as beguiled by her as Crowe's onscreen alter-ego William Miller (a pitch-perfect Patrick Fugit), the 15-year-old aspiring rock journalist covering the fictional band Stillwater in 1973 and discovering himself in the process, much to his overprotective mother's (Frances McDormand) horror. Billy Crudup's performance as guitarist Russell Hammond is an underrated turn if there ever was one, still sold short to this day. It's not easy playing the guy that crushes this kid's (and the audience's) dreams while somehow managing to escape as a pretty cool guy. That Philip Seymour Hoffman is most associated with his turn as rock critic Lester Bangs amidst a career of more substantial leading and supporting roles says everything about how memorably he played it. Bangs' advice to William on writing and criticism is hysterical, but made more hysterical by the fact that most of it's true.
It shouldn't come as a surprise the biggest worry revisiting this is Hudson, who's spent the better part of the decade attempting to completely erase this iconic role from our memories. Nice try, but not a chance. If you could win an Oscar for delivering a single line, she'd deserve it for the way she asks "What kind of beer?" showing a vulnerability and depth in this part we'd never glimpse from her again. She wasn't just "playing herself," as the results of her later work would unfortunately confirm. Unlike some other films on this list, I can't say this is a film where you necessarily discover something new on each viewing, but it does provide music and memories that don't easily fade away.
2. Wonder Boys (2000, dir. Curtis Hanson)
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Michael Douglas isn't usually a performer associated with projecting warmth and humanity, but as Grady Tripp, a pot-smoking, bathroom robe-wearing, creative writing professor in the midst of a mid-life meltdown, he reveals a hidden dimension to himself as an actor, stretching far out of what we've perceived is his comfort zone. During a chaotic rainy weekend at a Pittsburgh university he's clearing page 2,000 on the follow-up to his first hugely successful novel, "The Arsonist's Daughter" while dealing with his loony editor (Robert Downey, Jr.), an eccentric student (Tobey Maguire), another star student (Katie Holmes) with a crush staying under his roof and his frustrated mistress (Frances McDormand). Who knew Douglas could be so funny? Watching his exasperated, deadpan reactions to all the craziness surrounding him is priceless. Almost as priceless as the actual craziness. "Wordfest," Vernon, Marilyn Monroe's jacket, the Hollywood suicide list, the tranvestite, Rip Torn's silly lecture, the red cowboy boots, the Chancellor's dog. Every scene. Every joke. It all clicks. Comedy is hard but the actors (working from Steve Kloves' Oscar nominated script) make it look effortless and each hilarious moment is peppered with with small treasures and chestnuts intended for re-discovery. It's almost indescribable to anyone who hasn't seen the film how Hanson creates such a warmly inviting atmosphere you want to live inside and the city of Pittsburgh becomes as much a character as anyone else in the story.
While most movies about inspiring mentors almost always ring false and contrived, but when Maguire's James Leer is being hauled away by the cops and tells Professor Tripp he's the best teacher he ever had, considering the events that put him in that car to say it, you realize this is only film to actually earn the line. It's difficult to even pinpoint exactly what James, Grady or anyone else was going through but we still completely relate to them and understand, which is the mark of truly exceptional writing...in a story that's all about unexceptional writing. The trajectories Maguire and Holmes' careers have since taken should taint the picture, but it instead seems perfectly fitting for a story all about failing to meet expectations. That neither went on to the kind of success we anticipated adds a poignancy to the performances that weren't there a decade ago, making it almost impossible for me to be too disappointed in them. And that Robert Downey, Jr. did go on to that success, allows us to see one of his most enjoyable, underrated performances in a whole new light, while wondering how much of his personal demons he summoned up at the time to deliver it. It goes without saying Douglas was robbed at the Oscars but it's hard to get upset when the one statue the film did win belongs to Bob Dylan, whose music is so fully ingrained into the fabric of the picture he feels more like an honorary member of the cast than a soundtrack contributor. And by invoking the same mood and spirit his songs do it captures his music better than any story actually focused on the singer could.
Released in the shadow of my other favorite film about writing, Almost Famous, neither cleaned up at the box office, but it was Wonder Boys that actually flopped TWICE when re-released for awards consideration. Ironically now, this is the film that feels to me the more authentic and lived-in of the two, ten years aging it in ways I couldn't expect. You'd have to assume director Curtis Hanson was drawn to the material because he also felt the pressure of having to follow up on the enormous success he had with 1997's L.A. Confidential, a movie that has nothing on this. It knows that writers' are unusually in touch with quirky details and the humor does in a strange way seem directly aimed at them, which would explain its failure to strike a universal chord. Just more proof that great films can bring you close to a certain time, situation, characters or state of mind, but it's only the really great ones like this that actually bring you closer to you.
1. Into the Wild (2007, dir. Sean Penn)
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Detractors claiming that the film glorified its protagonist or didn't truly explore the negative consequences of Chris McCandliss' (Emile Hirsch) actions when in 1990 the Emory University grad burned all his cash and credit cards, donated his entire savings, and rechristened as "Alexander Supertramp," embarked on the journey of his life that that would eventually lead to his death. It's there on the street where we as viewers are forced to admit that no matter what his parents did or didn't do, he went too far, and regardless of how tempting it is to support his anti-materialistic philosophy, crossed the point of no return. His sister, Carine (Jena Malone) is now a victim and the people whose lives he impacted on the way to his final destination are officially casualties.
If there was ever a film destined to strike the critical and commercial jackpot it was Into The Wild but somehow it flew under the radar of audiences when it was released in 2007 with many unfairly accusing Penn of pushing some kind of an agenda. As if an endorsement of the picture would mean an endorsement of the actions or a left-leaning view in line with the director's politics. But the evidence points the opposite direction, with every character attempting to break through McCandliss' self-imposed emotional wall (you know it's a bad idea when Vince Vaughn is the voice of reason). From hippies Jan (Catherine Keener) and Rainey (Brian H. Dierker) to free spirit Tracy Tatro (Kristen Stewart) each chapter provides a chance for redemption that never comes because his trek to the "magic bus" in Alaska is just as much a misguided suicide mission as it is a life-affirming adventure.
Emile Hirsch never shies away from those harsher truths in his performance, which go beyond merely conveying pent up resentment or bitterness, but subtly hinting McCandliss might actually know just how misguided this whole thing is and still can't stop it. And neither can elderly leather maker Ron Franz, who Hal Holbrook justifiably won high praise and an Academy Award nomination for embodying in his brief, but unforgettable appearance. He's the supporting standout but each time I watch can't help but think that the most overlooked performance belongs to Jena Malone, who's our sensitive entrance way to the film at its start while also delivering invaluable voiceover work that acts as our guidepost through the story. It shoots a hole right through the popular theory that any use of voiceover narration is lazy.
Like others, I'm guilty of at first classifying the film as a purely emotional experience that wouldn't likely hold up to close critical scrutiny or repeated viewings. You'd figure a story that ends so tragically couldn't carry an urgent pull beckoning you back for more, but it does because from a technical standpoint it's unmatched. Every shot (lensed by cinematographer Eric Gautier) could be framed and mounted and Eddie Vedder's music is such a part of the journey it's difficult even envisioning the movie without it. How much the film editorializes or exaggerates the content of John Krakauer's book or even the real-life events doesn't interest me. But I do think the movie would have more fans if it were actually released during the early 90's period the events took place, when we would have been less cynical and more grateful Sean Penn even dared to ask the big questions, instead of arguing whether we agree on the answers to them. This film isn't just the most complete moviegoing experience of the decade, but the only one that feels monumentally important.
Recap:
1. Into The Wild
2. Wonder Boys
3. Almost Famous (Untitled: The Bootleg Cut)
4. Southland Tales
5. Donnie Darko
6. Zodiac
7. There Will be Blood
8. Punch-Drunk Love
9. The Squid and the Whale
10. Adaptation
Year-By-Year Breakdown:
2000-2
2001-1
2002-2
2003-0
2004-0
2005-1
2006-0
2007-4
2008-0
2009-0
Actors/Actresses Appearing in Multiple Films:
Brian Cox (2)
Robert Downey, Jr. (2)
Jake Gyllenhaal (2)
Jena Malone (2)
Frances McDormand (2)
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