The Oscar Quest: Reconsidered (Best Supporting Actor, 2003-2004)

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.


Alec Baldwin, The Cooler

Benicio del Toro, 21 Grams

Djimon Hounsou, In America

Tim Robbins, Mystic River

Ken Watanabe, The Last Samurai


This is a fun year to go back to. Because I always liked all the actors in this category but felt the category was kind of weak. So I wonder who else could have ended up here.

SAG — everyone but Djimon Hounsou. They had Chris Cooper for Seabiscuit instead. That’s one of those “Best Picture needs an acting nomination” situations. Though clearly that never stood a chance.

BAFTA — only Tim Robbins. Didn’t even win, either. Bill Nighy won for Love Actually. Which, how awesome is that? Albert Finney for Big Fish is probably the only legitimate choice there for a nominee.

BFCA — Four of five. They missed Hounsou as well in favor of Paul Bettany for Master and Commander. Who also caught BAFTA. He seems like a legit choice too.

Globes — six nominees, only three matched. No del Toro, no Hounsou. They had William H. Macy for Seabiscuit (really?), Finney for Big Fish and Peter Sarsgaard for Shattered Glass.

So damn. Hounsou came out of nowhere for that one. He really only had an Independent Spirit nomination. That must have been a huge surprise on Oscar morning.

And then, when you look at winners… Robbins swept the whole way through except BAFTA. So he was always winning this. That was never in question.

The Cooler is an interesting little film. I like that it caught on. I remember really enjoying it when it came out.

William H. Macy plays the world’s biggest loser. His luck is so bad that just being around him is enough to ruin your luck. Which is why he is employed by a casino as a “cooler.” He shows up at a table when someone has a hot hand and is up a couple grand, and he immediately kills all their momentum until they lose it all back to the house. And we follow him in this lonely life until eventually he meets a woman and falls in love. Which is unfortunate, because that causes his luck to turn, and people start winning when he’s around, which causes a lot of issues with his casino bosses, as you can imagine.

Alec Baldwin plays the owner of the casino where Macy works. He’s an old school owner, who remembers the good old days, where when someone was caught cheating, you took him out back and broke his fucking hands. Where his name was good enough to run the town, and he could get anyone anything and everyone owed him favors. He hates what happened to the town and is watching the whole thing sink from under him.

There’s a wonderful dichotomy to the character, where he does all these dirty, underhanded things to keep things going, but there’s also a genuine sense of caring there and you can see he’s doing it because he truly loves the business. The way he handles Paul Sorvino’s character, who is an aging singer who should not be performing at modern Las Vegas, tells you exactly who this guy is. He keeps Sorvino around even though he’s twenty years past his sell by date, pretends like he’s still a sex symbol, bringing panties he bought in the lobby and pretending like women from the show left them for him, and he keeps him supplied in drugs for his habit. He’s holding onto this dying way of life any way he can, but also because he loves it.

I really like this character and I think Baldwin is terrific in the role. Is this something I’d usually vote for? Not really. He’d probably make third, possibly second most years. Here, he contends with everyone else because the category is so weak. I could see maybe taking him here, given the rest of the category.

21 Grams is Alejandro Inarritu’s movie about drug addiction. I remember this coming out and being a big, classy Oscar film that “film” people liked because of the cast and because Inarritu was this up and coming filmmaker that they loved. But when I saw it, I didn’t love it all that much. I was very interested to go back and see this with a fresh perspective.

It’s an ensemble piece about people brought together after an accident. Kind of a precursor to Babel. Sean Penn is a teacher whose wife needs a heart transplant, Naomi Watts is a recovering drug addict who turned her life around, and Benicio del Toro is a reformed criminal and addict who turned to religion and now helps people in similar situations.

It’s an ensemble piece about people brought together after an accident. Kind of a precursor to Babel. Sean Penn is a teacher who needs a heart transplant, Naomi Watts is a recovering drug addict who turned her life around, and Benicio del Toro is a reformed criminal and addict who turned to religion and now helps people in similar situations. They all come together after del Toro accidentally kills Watts’ husband and kids in an accident. It’s a pretty good film. Don’t love it, but it’s solid.

del Toro is solid in the role. I don’t think he’s as good here as he was in Traffic, but you definitely get a sense of guilt from him and see how it rips him apart, gets him to start using drugs again and practically kills him. He’s very solid in the earlier scenes, though the performance falls apart for me in the third act — or I guess the theoretical third act, because the whole thing is non-linear — when Penn almost kills del Toro as an act of vengeance for Watts’ family, but then del Toro comes back and says, “No, please kill me, I don’t deserve to live,” and then it just devolves from there. That just does not register with me at all and kills a lot of the momentum for me for the performance. del Toro is definitely very solid, but I don’t know if I take him here. Which seems to be a recurring theme for this category. They’re all just kind of “okay” performances.

In America is my favorite Jim Sheridan film. I love it so much. It’s so beautiful in such a simple way.

It’s based a bit on his and his family’s experiences coming to America. His daughter helped him write it. It’s about a family that comes to New York from Ireland and is trying to assimilate into the culture. The mother is pregnant again, and they can’t afford another baby, and they’re still reeling from the death of a son a few years prior. And it’s just great. It’s almost a John Ford movie. It’s wonderful.

Djimon Hounsou plays the family’s neighbor. They know him as the “screaming man.” He’s always locked in his apartment, screaming. And he’s the one the kids are always afraid of, but eventually they work up the courage to knock on his door (to trick or treat), and he takes them in and is really sweet to them. And the family gets to know him and befriends him, and they learn all about him. He’s an artist who has AIDS and is slowly dying. And of course in the end, when the family has a lot of hospital bills to cover a difficult pregnancy, he pays them all when he dies.

Hounsou is an actor who is — I don’t want to say limited in what he does, but he definitely plays to certain levels most of the time. This one stretches those levels a bit and he makes Mateo into a really lovely character. I love this nomination, even though he really doesn’t much contend here. Like to see him nominated and a real joy to see any kind of support for this film, but maybe he’s a fourth choice here, possibly even fifth.

Mystic River is the movie that brought Clint Eastwood back into Oscar’s graces. Which is weird because it’s a pretty standard crime thriller that has not aged well at all.

Three friends are playing when one day a man pulls over, says he’s a cop, and orders them into his car. Only one goes, and it turns out the man is a kidnapper who holds the kid in a house and rapes him. Eventually the kid escapes. Cut to thirty years later and the three kids have gone onto way different lives. One is a cop, the other is a small time criminal, and the third, the one who was abducted, is a construction worker. The film picks up right as the criminal’s daughter is found murdered, setting off a chain of events that will of course lead to them interacting again and some shit going down.

Tim Robbins plays the kid who was abducted. But, you know, as an adult. Because playing him as a kid would be weird. He’s at the bar the night the girl goes missing, and for a while, it sure looks like he might have had something to do with it. He comes home with a hand wound and blood on his clothes. Which sure is suspicious. His story doesn’t seem to check out no matter how many times he tells it, and even his wife starts to suspect he may have murdered the girl.

Robbins is fine in the role. I never particularly loved this performance. I always thought the film was heavy handed and the actors we just left to do whatever they wanted. The scenes where Robbins is just himself, walking his kid to school, he’s fine. I even liked him. But the dramatic scenes, like where he’s telling his wife he doesn’t know who he is anymore, come off as almost laughable. Though, granted, he’s not Sean Penn level hamming it up. I can see giving him an Oscar for being Tim Robbins, but for this performance, I just wouldn’t vote for him. Though the problem with this category is — I might have to by default. This is one of the weakest Best Supporting Actor categories of all time. I might have to throw logic completely out the window and go on more than just pure performance.

The Last Samurai is an awesome movie. Sure, you don’t go into it for a historical lesson, but it sure is fun to watch.

Tom Cruise is a drunk, Civil War vet who has pretty much given up. He’s reenacting battle scenes for fairs and stuff. He’s hired to go teach the Japanese troops to fight as soldiers. Since they’re trying to nationalize and rid themselves of the samurai and feudalism. So Cruise does that, until he gets captured by the samurai after a battle and learns their ways, and realizes they’re actually the noble ones who are being slaughtered. So basically Dances with Katanas.

Ken Watanabe is the titular Last Samurai. Though one might argue Tom Cruise is that, and it’s a Mohicans type thing. But let’s say it’s Watanabe. He’s the wise, noble samurai warrior who would rather talk philosophy to Cruise than kill him. This is a tough performance to rate, because it’s both awesome and… kind of offensive. This is the same character as Cochise in Broken Arrow. The noble “savage” or foreigner or what have you who meets and befriends the white man, and becomes his ally as the white man adopts his ways, without fully giving up his white privileges.

The nomination is solid and is a nice way to bring Ken Watanabe over to America, but 1) he never had a shot at winning and 2) I don’t think he should have won. I might vote for him because I like him, but other than that, the performance is just okay.

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The Reconsideration: This is a really weak category, one of the weakest of all time. At least for me. When I don’t have anyone to vote for automatically, that to me signals one of the weakest categories of all time. This has maybe only happened five times, if that. But, we’ll see what we can do. I have to slightly alter my methodology for this one. I have to decide which performance I like best enough to vote for.

Benicio is the one person who had an Oscar already, so I’d think to take him off first, but in this category, his performance might be second for me. So I won’t immediately take him off, though given the different set of rules for the category, and me not really liking the performance enough to take it — I think he’s first one off.

Robbins would have been first one off, but I do like him and think he does deserve an Oscar, and in a category like this, that does rate consideration.

I think Robbins is better than Hounsou, but I like Hounsou’s character and film better, so that one’s a tossup for me.

Watanabe is solid, but I’m not sure I particularly love the performance enough to take it. He feels like a #4 for performance and a #3 for a vote. I’d rather take Robbins over him.

The only person I haven’t yet dealt with is Baldwin, because I both like his character and like his performance. And I think I have to take him. Because, of all these actors, I like Baldwin the best and think he’s worth an Oscar. Sure, Robbins is objectively worth one more, and I get him winning, but since I do also need to consider my favorite performance, that actually is Baldwin here, so I’m going to take Baldwin and feel a lot better about it than I did five years ago, where it felt more like a consolation prize. Here, I’m feeling pretty confident that Baldwin did give the best performance in the category. So that’s good.

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Rankings (category):

  1. Alec Baldwin, The Cooler
  2. Benicio del Toro, 21 Grams
  3. Tim Robbins, Mystic River
  4. Ken Watanabe, The Last Samurai
  5. Djimon Hounsou, In America

Rankings (films):

  1. In America
  2. The Last Samurai
  3. The Cooler
  4. Mystic River
  5. 21 Grams

My Vote: Alec Baldwin, The Cooler


In America is, in my mind, a perfect film. It’s not perfect, but I love it anyway. It’s so fucking great. I think it’s up there with Jim Sheridan’s best, and may be Jim Sheridan’s best. I cannot recommend this highly enough, and for my money, it’s essential. It’s not, objectively, but listen to me when I recommend things, they’re usually movies you’ll love.

The Last Samurai is an awesome movie that’s probably essential for movie buffs just because everyone else who loves movies has seen it. So just see it. The rest of us have, and we thinks it’s awesome as shit.

Mystic River is essential for Oscar buffs, highly recommended for film buffs because of the cast and how this crosslists with so many other people and things. I don’t love it enough to really recommend it. But you should just see it. It’s easier if you do. No real reason to skip this.

21 Grams is Alejandro Inarritu, which adds a certain level of essentiality to it. I don’t love it, but I like it, and the cast is great. Worth a watch for sure, but you don’t need to consider it essential or something you need to rush into. Get to it when you can. And if you don’t get to it for a while, you’re fine.

The Cooler is awesome. I recommend it. Not highly, but solidly. Definitely worth a watch and I think you should see it, though you don’t need to rush out and see it, all things being equal. There are more important things to get to first, but put it in the Queue and get to it eventually. You’ll enjoy it.

The Last Word: Robbins holds up. Let’s get that out of the way. The performance is whatever, but the category isn’t great, so he looks fine. It’s not Renée Zellweger. I personally think Alec Baldwin gave the best performance in the category and also would have held up, even though his film isn’t known as much as Robbins’. Watanabe probably would have looked bad, though maybe he’d have seemed okay. Hounsou wouldn’t have held up and neither would have del Toro have held up. del Toro having two could be good, but I don’t know if this role is the one to have won. I think Robbins was the best logistical decision they could have made, though I personally still side with Baldwin.

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Alan Alda, The Aviator

Morgan Freeman, Million Dollar Baby

Thomas Haden Church, Sideways

Jamie Foxx, Collateral

Clive Owen, Closer


This year felt like a two-person race all the way with the obvious choice being the veteran.

SAG had — Freeman, Foxx, Church. No Owen, no Alda. Their extra two were Freddie Highmore for Finding Neverland (Harvey gets those people on) and James Garner for The Notebook. Highmore stood a chance at a nomination (was probably #6) and Garner did not.

BAFTA had Owen, Foxx, Alda (which is how he got the fifth spot), and then Phil Davis for Vera Drake and Rodrigo de la Serna for The Motorcycle Diaries. Neither of those two had any chance at a nomination.

The Globes had everyone but Alda, and instead put David Carradine on for Kill Bill Vol. 2. That was never gonna happen, though he may have gotten a small amount of votes.

BFCA had everyone but Alda and nominated Peter Sarsgaard for Kinsey.

So, really, when you look at it all:

Freeman his SAG, BFCA and Globes, was in a major Best Picture contender. He was on.

Owen hit everything but SAG, but I feel like that was because the film missed a deadline, since no one was nominated there. He was clearly on.

Jamie Foxx was the one who hit everything, so he was a lock.

Church hit everything but BAFTA and was in Sideways, so there was no way he was getting left off.

And Alda had BAFTA, which put him and Highmore dueling it out for the fifth spot. Alda’s film having a higher profile and him being a beloved actor probably put him over the top there.

And then, once you get the category — Freeman vs. Owen. All the way. And Freeman winning SAG and being a veteran is what put him over the top. Though I feel like Owen was a fairly close second there.

The Aviator is Martin Scorsese’s film about Howard Hughes. Beginning with his foray into Hollywood and Hell’s Angels and Katharine Hepburn, we move into his aviation phase, and ending with his “crazy” phase.

Alan Alda plays Senator Owen Brewster, who is bought by Alec Baldwin and Pan Am to basically fuck over Hughes. He introduces a bill that gives Pan Am exclusive rights to the sky, then has the FBI raid Hughe’s house, knowing exactly which buttons to press. Eventually he makes him testify in open court, in front of the public and TV cameras, knowing he can’t stand being around other people.

Alda is great here, but has little to do in the film. A lot of this nomination felt like them needing a

Million Dollar Baby is a film that feels compromised by history. It’s great, and it moves you, but… Best Picture? I’m really curious how history remembers this. I’m too close to it all to really know. But anyway…

Hilary Swank is a 30-something wannabe boxer. She’s a girl, and she’s too old. No one wants to train her. She goes to Clint Eastwood’s gym. He’s gruff, but he has a heart. He eventually agrees to do so, because of her unrelenting spirit and tenacity. She eventually works her way up the ladder, eventually getting a championship fight. And then… well, if you don’t know the movie, things happen.

Morgan Freeman plays Eddie “Scrap-Iron” Dupris, Eastwood’s friend who helps him run the gym. Freeman mostly acts as a janitor, but is also Eastwood’s best friend. He’s the one who prods him to train Swank and… yeah, he doesn’t really have all that much to do. But he’s a good presence in the film and he gets a nice emotional ending, by taking over the gym from Eastwood and… well, the voiceover thing is a bit of… I guess we don’t need to get into that now.

He’s good. He’s solid. He’s Morgan Freeman. In this category, I get that he won. He was overdue and this was the perfect way to reward him. I’m not opposed to it. Do I think he gave the best performance in the category? No I don’t. Probably third best for me, top two for a vote. I can see taking him, and am fine with him winning, but he’s definitely not the best performance in the category.

Sideways is Alexander Payne. A movie that I’ve had to revisit so many times over the course of this Quest and given so many chances.

The short version is — I disliked this movie when it came out, and my dislike only grew over time when people went fucking nuts for it. Over ten years later and at least three or four watches, I’m at a place of, “Ehh, it’s okay.” Which is probably the best we can ask for.

Paul Giamatti and Thomas Hayden Church travel up to wine country for a bachelor party for Church. So they go, drink a lot of wine and hook up with women. That’s really the film. More stuff is going on, but not for our purposes here, really.

Church plays a former TV star who is now doing commercial voiceovers. He’s the opposite of Giamatti: he’s charming, he’s social, and he’s not afraid to say what he’s thinking. Even though he’s gonna get married, we see him start sleeping with a woman while up there, which blows up in his face.

I — Church is fine here, and he was definitely going to be nominated for it. He came from relative obscurity to being a memorable part of one of the best liked films of the year. Virginia Madsen was the same. I still don’t get what was so special about the performances, but to each his own. To me, he’s fourth. Maybe you can make a case for third. I don’t see how anyone takes him. But you know, maybe you see what I don’t in this movie.

Collateral is a really great film. Such a simple premise, yet really great.

Jamie Foxx is a cab driver who has a plan. Everything changes when Tom Cruise gets in the back of his cab. He says he has five stops to make, and at the end of the stops, he’ll give him $600, more than he’d make on a regular night. Foxx agrees. At the first stop, Cruise murders a guy. He then makes Foxx drive him to the rest of the stops, where he will kill four more people. The night spirals out of control from there. It’s a great, great movie.

Jamie Foxx and Tom Cruise are the leads of the film. Why Foxx went supporting is beyond me. But hey, he was clearly gonna win for Ray and was great here, so fuck it. I don’t care about the nomination, because the film is great and Foxx was great in it. But there’s no one suggesting he should have won this category, on performance or the fact that he’s lead, so it’s not a problem. He might be second for me in terms of performance, but he’s such a blatant lead I can’t even consider voting for him.

Closer is an actor’s paradise of a film. Four lead roles, relationship drama based on a play (which I’m sure won awards) directed by Mike Nichols.

I’m not sure how to explain the plot of this except — four people get involved in some way.

Clive Owen plays a doctor that Jude Law catfishes. He pretends to be Julia Roberts and sets up a Tinder date, basically. Only, turns out, Julia Roberts just happens to be there at that time, leading to an awkward encounter. But then they start dating anyway and get married. But that gets broken up when Roberts starts sleeping with Law. But then they end up back together anyway. Some stuff happens in between but there’s too much to get into.

Owen and Portman are the two best performances in the film, and Owen is, for me, the best performance in this category. Kinda surprised a little bit that he didn’t win, but I also get why Morgan Freeman was a better choice than him overall. Still, he was the best performance for me, and he’s the person I’m going to vote for. Simple as that.

– – – – – – – – – –

The Reconsideration: Let’s start by saying, this was the perfect year to give Morgan Freeman his Oscar. Because he had almost no competition. Jamie Foxx was gonna win lead (and he is a lead here), Thomas Haden Church was never seriously going to win (the nomination was more than a reward), and Alan Alda was a veteran nomination no one saw coming (and he came along with the film). He had no shot.

Clive Owen is the only one who could have made a legitimate case at this, and the Academy 1) didn’t really know him, and 2) was never really gonna take him because the film ended up with a softer reception than they were expecting. This was Freeman’s in a cakewalk, and I can’t say it was a bad decision.

Now, in terms of how I’d rate it:

Alda, I love, but I can’t in good conscience take him here. Church — I don’t really love Sideways. I think it’s okay at best. Even having seen it again deliberately for this reconsideration, I still don’t see the appeal of the film. He’s amusing, but at best I put him fourth. And even then I’d still want to take Alan Alda over him because I like Alan Alda more as an actor. So that’s where I stand there.

And Jamie Foxx is unabashedly a lead here and I’m not quite sure why they nominated him twice. I remember this year wasn’t all that strong, and there weren’t a lot of choices here, which allowed the outpouring of love for Foxx to spill over into this category. Which — sure. But there’s no way I can vote for him here.

It’s either Owen or Freeman. Freeman should have an Oscar, but for me, Owen was the best performance. So I take Owen. Gotta be honest about who is the best. Overall, I’d rather Freeman win, which is how he won. But Owen was better, so I’ll take him here.

– – – – – – – – – –

Rankings (category):

  1. Clive Owen, Closer
  2. Jamie Foxx, Collateral
  3. Morgan Freeman, Million Dollar Baby
  4. Thomas Haden Church, Sideways
  5. Alan Alda, The Aviator

Rankings (films):

  1. The Aviator
  2. Collateral
  3. Million Dollar Baby
  4. Sideways
  5. Closer

My Vote: Clive Owen, Closer


Million Dollar Baby is an essential film. Best Picture winner, and… yeah, it’s well known in the culture and all of that. Essential for film buffs. I don’t think I need to qualify this all that much.

The Aviator is a Martin Scorsese film, and Martin Scorsese films are essential, especially the really famous ones. The only ones are negotiable are the pre-Mean Streets ones, Kundun, After Hours, and maybe one or two others. That’s about it. The rest, you need to see.

Collateral is, in my mind, an essential film. Is it? I don’t know. But fuck it, I make the rules here. And 90% of film buffs will love this movie, so you see it on that alone. It’s fucking great.

Sideways is an essential film. Alexander Payne has crafted a filmography that has proven itself to be essential all around (at least, from Election forward). That’s how it is. You see them. It’s what you have to do as a film buff. The good news is, you’ll probably really like all of his films.

Closer is good, but not essential. I recommend it for the performances and for talking about these categories. But otherwise you only need to see if it you like the actors in it or love Mike Nichols.

The Last Word: Freeman holds up fine and was probably the best choice in terms of how it looks historically. Owen gave the best performance in my mind and really should have won on those grounds. Foxx is right up there, but he was winning lead and is really a lead in this film too. Don’t think Church holds up at all and Alda is just there as a veteran. Owen and Freeman are the best choices, and while Owen gave a better performance, Freeman is the better historical choice, so I’m okay with it.

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(Read more Oscar Quest articles.)

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