The Oscar Quest: Reconsidered (Best Supporting Actor, 2007-2008)

The Oscar Quest began in May of 2010. I finished about fifteen months later, and wrote it up for this site. That was essentially the first thing I did on here. Five years have passed since then. I’ve grown as a person. My tastes have changed, matured (or gotten more immature, in some cases). So it feels fitting, on the five year anniversary of the site and of the Oscar Quest, to revisit it.

I want to see just how my opinions about things have changed over the past five years. I didn’t do any particular work or catch-up for this. I didn’t go back and watch all the movies again. Some I went back to see naturally, others I haven’t watched in five years. I really just want to go back and rewrite the whole thing as a more mature person, less concerned with making points about certain categories and films than with just analyzing the whole thing as objectively as I can to give people who are interested as much information as possible.

This is the more mature version of the Oscar Quest. Updated, more in-depth, as objective as possible, less hostile. You can still read the old articles, but know that those are of a certain time, and these represent the present.


Casey Affleck, The Assassination of Jesse James by the Coward Robert Ford

Javier Bardem, No Country for Old Men

Philip Seymour Hoffman, Charlie Wilson’s War

Hal Holbrook, Into the Wild

Tom Wilkinson, Michael Clayton


This was an interesting year, because certain performances/actors fluctuated between lead and supporting. For instance, Tommy Lee Jones was also nominated by SAG for No Country. BAFTA nominated him there too. But the Academy instead put him lead for In the Valley of Elah (which no one had really seen at the time, and no one’s really seen since). SAG ended up missing Hoffman for that.

BAFTA missed Holbrook (understandably) and Affleck, which also makes sense. They had Paul Dano for There Will Be Blood (who really didn’t get as much traction as the role and the performance would suggest).

The Globes missed Holbrook in favor of John Travolta for Hairspray. So there’s that.

And BFCA nailed the category cold.

Once the nominations went through, Bardem swept every single one of them en route to an easy win. There was never any doubt in this category once the nominees were finalized.

– – – – –

The Assassination of Jesse James by the Coward Robert Ford is to me, one of the best westerns ever made, and it’s perfect from beginning to end.

It’s about… well, the title pretty much tells you what it’s about. Jesse James’ gang is wanted by the cops, and most of the original members are dead or arrested, so he’s forced to hire people he wouldn’t normally trust, including Bob Ford and his brother Charlie. And we watch over some months until the inevitable happens. It’s a brilliant mediation on the western genre and it’s really quite an amazing film.

Casey Affleck plays Bob Ford, and he is the lead of the film. Brad Pitt as Jesse James got billed as lead, but he has less overall screen time than Affleck does. They’re kind of co-leads. Though honestly, Pitt could have ended up here too.

Affleck is really terrific in the role and the only thing that gives me pause is the fact that he’s so clearly the lead of the film. Other than that, he’s as up there as anyone can be in this category. He gives a great performance that shows you exactly who this guy is and what drives him to killing his idol.

No Country for Old Men is the Coen brothers doing Cormac McCarthy. I’m still surprised, nine years later, that this won Best Picture. I still don’t get how that happened. Sometimes the Academy makes one of those choices that seems too smart and cool for them.

Josh Brolin is a guy who, while hunting, stumbles upon the aftermath of a drug deal gone bad. There’s a case with $2 million in it and a dying man. He takes the case and leaves the dying man. Only his conscience gets the best of him, and he goes back to bring the dying man some water, which sets him on the path of being followed by Javier Bardem.

Javier Bardem is a fucking stone cold killer. Where he goes, death follows. From his opening scene, where he flips a coin to decide whether someone lives or dies, he’s the most riveting thing on the screen. There’s something so fascinatingly brilliant about this performance, and he of course swept every category this year en route to the win. And honestly, even though this category is really strong, I can’t really argue against it.

Charlie Wilson’s War is a film that I love, even though it’s compromised on a lot of levels (namely in its ending, which lacked the bite of Sorkin’s original script).

It’s about a congressman who decides to help Afghan soldiers fight against the Russians by providing them with weapons. So he goes around, slowly making friends around town and overseas, and quietly raising the budget for the subcommittee through various ways and means. Mostly it’s about a random drunk congressman who chases women who manages to turn the tide of a war simply by making friends with the right people at the right time.

Philip Seymour Hoffman plays Gust Avrakotos, a CIA agent, who is one of four guys assigned to the “Afghan desk” to plot a strategy for helping them defeat Soviet forces. Wilson meets with him and the two of them work together. That’s the broad strokes. The actuality — Hoffman is fucking great in the role. His first scene is one of the greatest character introductions I’ve ever seen.

These three minutes are the first time you see him, and after this, you want him to be in every scene in this movie:

Every scene he’s in is absolutely perfect. He’s hysterical. Not sure you can actually take him in this category, but fuck, is he by far my favorite performance. He’s just a joy to watch in this (and everything really). I love this character. He’s by far the best thing in the film.

Into the Wild is Sean Penn, and probably his best film. This was a great one and if they had more than five nominees, this would have made it on there. 2007 was actually one of those years where you wish they had ten nominees, because there were so many great choices for them.

It’s about Chris McCandless, who decided to drop everything after college and go travel the world with no money and no car, even. Just hitchhike and go wherever. Eventually he dies of starvation in Alaska, but in between, he did pretty well.

Hal Holbrook plays an old man Chris befriends along the way. His family died in a car crash, and he’s alone. Chris stays with him for a while and he teaches him how to make leather belts and things, and really takes him in as a son. And eventually he even offers to adopt Chris, wanting him to stay. But Chris wants to go off to Alaska, so Holbrook gives him a bunch of gear he can use.

It’s a nice performance. Holbrook is such a sweet presence and does a great job in the emotional scenes (telling about his family and offering to adopt Chris), but he’s no better than fifth in the category. You might like him higher than that, but he’s clearly fifth choice. The category’s too strong to really consider him.

Michael Clayton is a wonderful film. Hearing the title and the logline, I thought this would just be a solid thriller and nothing more. But shit, is this a great movie.

George Clooney is a fixer lawyer who makes problems go away. We start with him almost being assassinated and flash back from there to how we got where we are. Which involves a pharmaceutical company embroiled in a lawsuit for killing people with their product and them knowingly covering it up.

Tom Wilkinson plays Clooney’s mentor, who was on the case for the company for years and years, until one day he has a breakdown mid deposition, taking off all his clothes and ranting. And Clooney’s sent to figure out what the fuck is going on. And the company worries about him, since now he’s seemingly lost his mind and is ranting and raving, but also knows all the dirty secrets. So they don’t know what to do. Which eventually means they hire people to kill him.

Wilkinson is really great here. He plays the guy perfectly, and you totally understand his journey from beginning to end. Though he’s one of those guys where you go, “Of course you nominate him, he’s great,” but then once he gets nominated, there’s really no chance you actually vote for him. He’s really solid, but there’s always someone everybody likes better. He never manages to go higher than third for anybody. Which sucks. But it’s a hell of a performance, so he has that going for him.

– – – – – – – – – –

The Reconsideration: Okay, here’s the deal with this one:

Wilkinson is great, and in a weaker year, he’d contend very highly for a vote, but here he’s just solid. And Holbrook is a veteran nomination that looks nice but is just okay. He’s bolstered by the strength of his film more than anything.

Philip Seymour Hoffman is by far my favorite performance in the category. Is he the best? No. But he’s the most entertaining, and I love him in Charlie Wilson’s War. Still wouldn’t take him, and I don’t know if there’s a bigger champion for that film and that performance than me.

Casey Affleck is the LEAD of the film. And this is as blatant a category fraud as you’re gonna get. I have a hard time voting for him because of this, despite the fact that he is undoubtedly great in the film.

Now, Javier Bardem — one of three leads. But objectively, in this category, he has enough screen time to qualify as supporting. Plus, so much of his performance is creating the air of creepiness and omnipresence that works. Not to mention he’s become one of the most iconic villains of the past decade. So right there, he’s the vote.

– – – – – – – – – –

Rankings (category):

  1. Javier Bardem, No Country for Old Men
  2. Casey Affleck, The Assassination of Jesse James by the Coward Robert Ford
  3. Tom Wilkinson, Michael Clayton
  4. Philip Seymour Hoffman, Charlie Wilson’s War
  5. Hal Holbrook, Into the Wild

Rankings (films):

  1. The Assassination of Jesse James by the Coward Robert Ford
  2. No Country for Old Men
  3. Charlie Wilson’s War
  4. Michael Clayton
  5. Into the Wild

My Vote: Javier Bardem, No Country for Old Men


No Country for Old Men is 100% essential, and I think we all know this. No film buff would EVER skip a Coen brothers movie. Let alone one that won Best Picture and Best Supporting Actor. This movie is incredible and everyone should (and probably has already) seen it.

The Assassination of Jesse James by the Coward Robert Ford is one of my ten favorite films of all time. So this is one of those few times where I pull the card of, if you like movies, and you haven’t seen this one, we can’t be friends. Because this movie is incredible. It’s unlike any western you’ve ever seen, and there’s no reason for any self-respecting film buff to not have seen this movie. I don’t pull this card often, but trust me, it’s for your own good.

Michael Clayton is great. If you’re just getting into movies, and you haven’t seen this, then see it. And if you have seen it, but haven’t really gotten too far into movies yet, then boy, are you gonna love the 70s. This film is essential for all film buffs. You’ll love it. Must see because it just is. It’s an IMDB kind of film. You call it essential because you know 85% of people will love it. Make them see it so they realize it.

Charlie Wilson’s War is such a fucking entertaining movie. I can’t call it great, because there are compromises all over it. But man, is it fun. I can quote this movie all day and think everyone should see it. I don’t think anyone should ever skip a movie written by Aaron Sorkin.

Into the Wild is similar to Michael Clayton in that — it tests well on the popular vote/IMDB scale. So let’s call it essential because it’s great and you’ll probably love it. It’s not all-time essential, but as far as last decade goes, completely essential.

The Last Word: To me, Bardem is the vote. If you don’t mind category fraud then Affleck is also a very fine alternative. Barring that — I obscenely love Hoffman’s performance but even I wouldn’t take him in this category, and Wilkinson can actually be considered worthy of a vote too. But I feel like Bardem has proved himself to be most worthy owing to how iconic the character has become. I think they made the right choice here.

– – – – – – – – – –

– – – – – – – – – –


Josh Brolin, Milk

Robert Downey Jr., Tropic Thunder

Philip Seymour Hoffman, Doubt

Heath Ledger, The Dark Knight

Michael Shannon, Revolutionary Road


Heath Ledger was never losing this category. That takes care of that part.

The more interesting part to talk about is how this category came about.

SAG had 4/5, missing Michael Shannon in favor of Dev Patel for Slumdog. Which made sense, since Oscar likes to have their Best Picture get at least one acting nomination. And Patel made sense, even though it would have been blatant category fraud. (Though not quite, since there are three different actors who play him, and he is only on screen part of the time. Though his character is the lead, so it’s some murky waters, the whole business.)

BAFTA missed Shannon and Brolin in favor of Brendan Gleeson for In Bruges (love that) and Brad Pitt for Burn After Reading (which I am SO in favor of).

The Globes missed the same two in favor of Tom Cruise for Tropic Thunder (never gonna happen) and Ralph Fiennes for The Duchess (ehh). BFCA had Brolin but also had James Franco for Milk instead of Michael Shannon.

Shannon came completely out of nowhere but looks pretty good now that he’s such a respected and solid actor.

This was a category with three locks and two open spots. This must have been a hard one to pick at the time. I guess most people would have put Patel here as one, because no one could really have seen Shannon coming, and either Brolin or Franco would have made sense as the fifth nominee. But fuck if I know how you pick that one. This was before my time.

– – – – –

Milk is pretty easy. Biopic of Harvey Milk, the first openly gay elected official in the United States, from his time entering politics to his eventual assassination. Sean Penn is sublime in this movie and well deserved his second Oscar for it.

Josh Brolin plays Dan White, the man who killed Milk. He’s on the same board as Milk, and the two are polar opposites. Brolin is a religious war vet who is very conservative. They attempt to work together, but their viewpoints are so different they end up disagreeing on almost everything. White wants to prevent a psychiatric hospital being built in his district while Milk wants a gay rights bill to be passed. And over time, as Milk votes against so many of his proposals, he starts to hate him. And then eventually he resigns, only to come back and shoot Milk one day.

Brolin is terrific in the part. You can see his inherent homophobia as well as his legitimate attempts to find a common ground with Harvey. And then later on, you see him slowly start to become more unhinged, leading to the eventual assassination. It’s a quiet, layered performance that is well worth the nomination. Though I think we can all also agree that he got this half due to the performance and half because of No Country the year before this. Him also playing George W. Bush this year also didn’t hurt.

He’s solid here, but I don’t put him any higher than fourth in the category. He had no chance with this one. The nomination is the reward.

Tropic Thunder is one of the great comedies of the past decade. I knew I was gonna love this from the start, and the minute the fake trailers began in the theater, I knew I was in the right place. It’s just a great movie.

It’s about a war movie being shot overseas, which is going horribly over budget and over schedule. All the actors are involved in their own shit and no one seems to want to help the movie get made right. So the director decides to really scare the actors — put cameras all over the jungle and then leave the actors there to act. Only, the director steps on a landmine and dies and now the actors are in the jungle for real, not realizing everything that’s happening to them is for real and not part of the film.

Robert Downey Jr. plays Kirk Lazarus, multiple Academy Award winner and complete method actor. We see him preparing to play Sgt. Lincoln Osiris, a black soldier in Vietnam. To do this, he gets his skin pigmented to look like a black man. Literal blackface. And he’s so deep into character that he refuses to drop it for the duration of the shoot. (Not until the DVD commentary, man.)

He’s the funniest part of the movie. This is a character that could go so wrong, and yet the way Downey plays it, it works completely. The nomination is totally unnecessary but I support it completely. I fucking loved him in this and this is one of the great comic characters of the past twenty years. This was their way of welcoming him back in the fold (since they couldn’t nominate him for Iron Man). And we got an awesome performance nominated to boot. No chance at him ever winning this, but I love that he’s here with every ounce of my being.

Doubt is based on a Pulitzer Prize winning play, and it shows, based on the talents they got to be in this. Meryl Streep, Philip Seymour Hoffman, Amy Adams and Viola Davis.

It’s about a nun at an all boys’ catholic school who suspects a priest of having inappropriate relations with one of the boys. And she takes her suspicions to the old-school head nun, who does everything she can to smear the name of the priest, assuming he did it because she disagrees with his more progressive style.

Philip Seymour Hoffman plays Father Flynn, the priest in question, and while you’d think he’s a lead, there’s actually a compelling case to be made for him belonging in supporting. He also wins this if not for Heath Ledger. He’s fucking fantastic in this too. He plays the character in such a way that you could argue both sides. You could say, “Of course he did it,” and “Of course he didn’t do it.” And he’s really strong in this part. It’s an actor’s showcase, and honestly, were it not for a clear winner, he’s my vote. He’s that good.

The Dark Knight. You’ve seen it. We’ve all seen it.

Heath Ledger plays the Joker.

Pretty sure we all agree he wins this in a landslide.

Revolutionary Road was one of those January Oscar films. The ones you peg a year out as a major contender at the Oscars. So few of them hold up. And this was one of those casualties.

It’s based on a famous novel, directed by Sam Mendes (who already had a Best Picture win under his belt) and starred Kate Winslet (loudly overdue for an Oscar at that point) and Leonardo DiCaprio. That movie screams Oscar. But no one seemed to love it and it quietly faded away, only getting this (very much a surprise) nomination and two other nominations for Production Design and Costume Design.

It’s about a couple raising a family in Connecticut in the 50s, and dealing with their own personal problems an such.

Michael Shannon plays the son of their neighbors, who has been declared insane and institutionalized. The point of the character is that he’s the only one who gets to speak his mind about how hypocritical everyone is and how bullshit all these social conventions are. He’s the powder keg in an otherwise staid film. So I get the nomination. He’s nothing more than fifth in the category. He’s only in a handful of scenes, and while he makes an impression, you don’t take him over anyone else in this category.

– – – – – – – – – –

The Reconsideration: As much as I’d want to vote for Robert Downey Jr. on pure entertainment value, Heath Ledger wins this and no one would ever argue that decision. It’s one of the best performances ever put to screen. It’s perfect.

– – – – – – – – – –

Rankings (category and films):

  1. Heath Ledger, The Dark Knight
  2. Philip Seymour Hoffman, Doubt
  3. Robert Downey Jr., Tropic Thunder
  4. Josh Brolin, Milk
  5. Michael Shannon, Revolutionary Road

My Vote: Heath Ledger, The Dark Knight


The Dark Knight — do I really have to say it?

Doubt is terrific and I’m calling it essential because there’s no reason for anyone who likes movies not to see it. Meryl Streep, Philip Seymour Hoffman, Amy Adams and Viola Davis in a movie version of a Pulitzer Prize winning play. What more could you possibly ask for?

Milk is probably essential. It hasn’t held up as well as you’d think. But it was a great film then and hasn’t become less great. Plus Penn won for it. So that makes it somewhat essential. At worst it’s a very high recommend. But since we’re within ten years, I’m continuing to call it essential. Just see it. It’s wonderful.

 Tropic Thunder has held up as one of the best comedies of the past decade and to me, is an essential film. It’s not, objectively, but as far as comedies go, this one is pretty well liked and quoted by people around my age group. Time is the only thing that’ll tell if it’s really essential, but if I were making the list, I’d say you need to see this because it’s absolutely hilarious.

Revolutionary Road is a film that seemed like a major Oscar contender, but then fizzled out. I remember people being really disappointed by it. But I thought it was terrific. I thought the performances were great and it was really solid. At most, though, it’s just a solid recommend because of all the people involved (DiCaprio, Winslet, Shannon, Mendes and Deakins). Not essential in the least. But with those people involved, why wouldn’t you check this out?

The Last Word: It’s Heath and no one else. This is one of the best decisions they ever made. Totally deserved, and the category is really strong to boot.

– – – – – – – – – –

(Read more Oscar Quest articles.)

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