The Jay’s Official 2009 Oscar Predictions



Slumdog Millionaire seems to be a lock, after winning most every pre-Oscars award there is, including the Golden Globe. But MILK is rising in favor. Entertainment Weekly even called MILK the upset winner. I had to force myself to sit through it, and though I found it to be homework, it’s definitely well-made homework, with a great performance by the Pennster (whom I usually loathe). Benjamin Button sure LOOKS like a Best Picture winner, but feels more like one of those epic prestige films that are made to win, but never do (I’m thinking about films like The Painted Veil, Atonement, anything Kate Winslet appears in). Frost/Nixon is forgettable and was probably only nominated because everyone believed they were just supposed to, and did. The Reader is the dark horse, and we should all be frightened by it. If a tiny Nazi movie with some token Kate Winslet nudity can steal a spot from the infinitely more deserving The Dark Knight, who knows what other movies it could topple.

Who Should Win: MILK – The Academy loves a rousing biopic about a tragic figure and a controversial topic. See: A Beautiful Mind, Gandhi. Also, the Academy owes the gay population one for letting Crash beat Brokeback Mountain. And, in a year of relatively classic-free movies, Slumdog Millionaire losing would be less of an upset than people think.

(Full disclosj: The Wrestler was the best film of the year, IMHO. Iron Man was my fav movie.)

Who WILL Win: Slumdog Millionaire – A Bollywood musical about the game show “Who Wants To Be A Millionaire” that is by turns uplifting, inspiring and ultra-violent; that overcomes the obstacles of having no stars, an awkward title and did I mention the Bollywood musical part (?); that ends up being a massive critical hit and grossing HUGEmongous box office? Now, THAT’S what I call a Best Picture winner!


It’s between Sean Penn and Mickey Rourke, this is fact. Brad Pitt was good, but heaping helpings of CGI old midget Brad, and CGI young hot Brad diminish his performance. Also, the movie was ultimately blah, which means HE was ultimately blah. Richard Jenkins should be happy just to be nominated; this is a career achievement for a well-regarded character actor. In any other year, Frank Langella would be in the driver’s seat, but unfortunately he’s up against too strong a field (and people haven’t forgotten that he was Skeletor in the Masters of the Universe flick.). Sean IS fantastic, but he’s done work just as good in other movies; his personal bar is set so high, I don’t believe he cleared it. Mickey Rourke IS The Wrestler. He IS that movie. Every second of the film belongs to him, and he commands those seconds. His is a riveting performance, filled with pathos, humility and dark humor. It’s the best of the year.

Who Should Win: Mickey Rourke – For all the reasons above, and for this: his is a great story. And we love a great story at the Oscars. The one in a million shot, the newcomer, the aging veteran and the comeback; those are the classic stories, and Rourke fits into three of them. Also, imagine the speech he would give!

Who Will Win: Sean Penn – That being said, does Rourke have the votes to win? The Oscars are a political campaign more than anything; you need to shake a lot of friends, make a lot of promises, be nice and be diplomatic. Anyone paying attention to the sound bites that keep coming from the Rourke camp knows he’s one more Chihuahua sneeze from turning a dance floor into a circus. And Sean Penn has a LOT of friends in this town.


Anne Hathaway the Langella of Best Actress nominees, a stunning performance offset by audience indifference to the film itself. The fact that people think Winslet is OWED an Oscar, makes me sick. This isn’t a cumulative contest; it’s based on one performance, the performance you are nominated for. Kate Winslet may be the best actress of our generation, but she is not owed an Oscar. Too bad I haven’t seen The Reader, so I can’t say one way or the other if she was “better” than Anne Hathaway. Meryl Streep was great in Doubt, but she was over-directed, left a bit too much to her own devices, devices that caused her to overact throughout most of the film. Also, Cherry Jones apparently did a better job in the Broadway play. Melissa Leo is the Richard Jenkins, a fine character actor justly rewarded for fine, understated work. And Angelina? Please.

Who Should Win: Anne Hathaway – Blowing away her Disney typecasting, announcing her presence as a new, substantial dramatic leading lady, Hathaway tears through the film, a whirling dervish of venom and rage. But it’s her quiet moments that did it for me, the speech about her brother’s death, how she confronted her Mom about her brother. Slapping the buh-geez-us out of Debs Wings. Stunning work.

Who WILL Win: Because, much as it pains me, the Oscars ARE a cumulative contest, and Kate IS owed an Oscar. I just wish she wasn’t so blatantly campaigning for it.


Heath Ledgsnore. OK, look: yes, he was good in The Dark Knight. But, BUT, the part is a lay-up. It’s The Joker! There is 50 years of material on him. He’s a showy psychopath who gets all the good lines. Obvs course Ledger crushed it! Anyone would have! Are we seriously giving him this Oscar JUST because he died? You’re telling me Michael Shannon wasn’t as explosive? PSH less powerful? RoDo JU not as funny? Josh Brolin less Brolin-y? Can we please ease back on the Heath Ledger pedestooling? Besides, Eckhart was better, anyway.

Who Should Win: Michael Shannon – There wasn’t a more electrifying presence on film this year. Not even for a frame of film.

Who WILL Win: Heath Ledger – Let’s just get this done, so I can stop looking like the asshole disrespecting the dead.


I actually LIKE all five of these actresses, yes even Penelope, and think they are all equally deserving of the statue. You have to be pretty effing great to stand out next to PSH and Meryl Streep, but somehow both Amy Adams and Viola Davis pulled it off. Each have quiet, masterful moments, and affect the film in a tangible way when they’re on screen. Unfortunately, they’re going to cancel each other out. Taraji is the dark horse; her work is tender and lovely in Ben Button, but I don’t think she has the one big scene or speech to push her over the top. Marisa. Marisa is not winning. And for one reason: “Two-Time Academy Award Winner Marisa Tomei”. Never. Not in a million years.

Who Should Win: Viola Davis – When you come on for one scene, ten minutes, steal the movie, turn it flip it and reverse it, give it back to the leads and leave quietly? That’s a supporting role. No other actress in this race affected her movie the way Viola did.

Who WILL Win: Penelope Cruz – Doesn’t she seem like she just SHOULD have an Oscar by now? We all agree she was luminous and crazy and awesome in VCB and that her work with Pedro is stunning, but will never be rewarded, so let’s get her Oscar out of the way so I can stop being the asshole who disrespects the woman who can’t seem to learn English after living here for 15 years.


Well, this will be quick. Danny Boyle is winning this award. Period. David Fincher probably deserves it from a technical standpoint, as his Ben Button is a masterpiece of craft, though not of storytelling. Stephen Daldry, nominated for every movie he’s ever made ever, will win one of these down the line, so no worry there. Ron Howard is a zzzzzzzzzzzzzzzzz. Gus Van Sant did an admirable job documenting the life of Harvey Milk, but the film was far from transcendent.

Who Should Win: Christopher Nolan – Captaining a $200 million ship through the rigors of production, the death of one of this stars and a bleak, cold story into the harbor of massive critical and commercial success, while at the same time actually creating a dynamic, intricately layered film (not movie) is grounds for this award if I’ve ever seen it. Put another way, if James Cameron and Peter Jackson won their awards for doing the same job as Nolan, why shouldn’t he win? Hell, why wasn’t he nominated???

Who WILL Win: Danny Boyle – For all the reasons Slumdog Millionaire is winning Best Picture, Danny Boyle is winning Best Director.


MILK is winning; the degree of difficulty was too high. WALL-E is getting its dues in the Best Animated Feature category. Frozen River has been seen by nobody. Literally no one has actually seen this movie. Even the director of Happy-Go-Lucky hasn’t seen THAT movie. And no one can understand anything said in In Bruges, enough to decide its true worth.

Who Should Win: Wall-E – writing silence is harder than writing dialogue. And writing robots instead of humans is even harder. But writing robots and silence instead of people and words? The Hardest.



Doubt and Frost/Nixon got their lauds on the stage, and don’t an Oscar to say they’re great works of writing. Ben Button is Forrest Gump the sequel and Eric Roth already won an Oscar for the first one. “Kate shows her tits” is not difficult writing, so no dice on The Reader. How can Slumdog Millionaire not win? The elements are outrageous, the cohesion is stunning and the inspiration it gives audience is without equal in this race.

Who Should Win: Doubt won the Pulitzer Prize. An Oscar is a step down.

Who WILL Win: Slumdog Millionaire.


Animated Feature: WALL-E

Art Direction: Ben Button

Cinematography: Ben Button

Costume Design: The Duchess

Documentary: Man on Wire

Documentary Short: The Witness

Film Editing: The Dark Knight

Foreign Language Film: Waltz With Bashir

Makeup: Ben Button

Music (score): MILK

Music (song): “O Saya” – Slumdog Millionaire

Short Film Animated: Presto

Short Film Live Action: On The Line

Sound Editing: The Dark Knight

Sound Mixing: Ben Button

Visual Effects: Ben Button

Good luck in your Oscar pools!


About Jason Matthews

Jason Matthews is the head writer for The site has been nominated for two Weblog Awards (Best Culture Blog, 2006 & 2007), and has been featured on more than 100 websites, including the IMDB, Defamer, College Humor, USA Today’s Pop Candy (Written by Whitney Matheson), Entertainment Weekly’s PopWatch,, Gorilla Mask and eBaum’s World. Jason is also an accomplished playwright. He is currently the Writer-in-Residence at the Ruskin Group Theatre, where through their showcase “Café Plays”, he has written and produced forty-five one-act plays, and premiered his full-length debut comedy ‘Four Night Stand’ to a sold out six-week run in Spring 2010. In addition to his work online and in theatre, Jason was the host of PopLoad on from January – May 2007, and was the Editor-in-Chief of the popular Santa Barbara-based arts magazine CampusPOINT from June 2000 – June 2002. He has a Bachelor’s Degree in Film Studies from UC Santa Barbara, and an intense love for Ben Affleck and Keanu Reeves. Find Jason Matthews on Twitter @
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