The 25 Best Movies of the Century: No. 25 - ‘Michael Clayton’

0:00This is Bill Simmons, and I want to tell you about my movie podcast, The Rewatchables. where each week I'm joined by Ringer movie lovers, Chris Ryan, Sean Venasy, Van Lathan, Kyle Brandt, Natalie Rubin. We have a whole bunch of people on. We talk about movies we can't stop rewatching. And now you can watch us cover these movies on video in the Spotify app. We have covered over 350 movies, including Heat, Goodfellas, Boogie Nights, Pulp Fiction. We have some real heavy hitters coming up here in 2025. Make sure to follow us on Spotify where you can watch every new episode right now. Just head to the rewatchables on Spotify, now on video.

1:05I'm Sean Fennessey. I'm Amanda Dobbins. And this is 25 for 25, a big picture conversation special about Michael Clayton. That's right. We are kicking off our year-long project, counting down the 25 best slash our favorite films of the century so far. We're doing it with a bag man today. We're doing it about Michael Clayton. We have to talk about 25 for 25 before we dig into this movie for this mini episode, this semi-bi-monthly episode. How often are we going to be doing these? Well, you're the one who made the spreadsheet, but it seems like every other week. More or less. Yeah. More or less. Maybe twice a month, sometimes three times a month.

1:46Sometimes we'll cluster because, you know, there are movie events, personal events. But yeah, we'll be throughout the year because we have 25 films, plus a couple bonus episodes, one of which might be in the can already. Yes, a selection committee. Yeah. Sort of the Selection Sunday style. It's March Madness. Yes. It's just starting now. We had our own version of it last week. So, and they will be rolling out until December. So 25 for 25, what is it? I've already sort of explained what it is, right? Right. It's a collaboration. You and I came together, meeting of the minds. What are the best movies that we can agree on that represent our taste?

2:25What the century in cinema is so far? Where things are going, where they were? What else? What does this constitute? It is the big picture's 25 most important movies of the century so far. And so if you've been following along with the show, you understand some of the implications, the preferences that are implied in that. But we probably should lay them out a little bit so people don't yell at us like deeply. We have some rules. We do. The first rule is that there's one film per director. Correct. So, you know, we don't have five Tarantinos. We don't have five Finchers. Like, you and I could have done that, but that is a very boring list.

3:10So one film per director. Your blood pressure is already rising. Well, that was a very hard thing to accomplish. And we've still said that there's an outside chance that we could make some changes, even though, in theory, our list is locked right now. Yes, we're not going to change that rule. No, no. But we can make substitutions. we cannot undo the ranking after it's been announced. Once an episode's out, the list is locked to that point. But with the things that are not announced, we can still be editing. How much last minute swapping do you think will happen in the top 10? Zero? I think zero, but those 10 have to be in the top 10.

3:54It's like we can't cut one of those. I don't know. I don't know. What if we do? I think I'm already really angry. We can't. I don't know. 10 through 20 is probably where things are going to get a little crazy. We shall see. I don't know. I know you really fought for King Richard. You felt like Will Smith's performance in that film is really important. You had it at number nine right now. So we might have to make a change there. There's not a ton of other rules. The films need to be released starting January 1st, 2000, domestically in the United States. Yeah. All the way up until ongoing. This is a current project.

4:31So if a film hits when a Minecraft movie comes out in two weeks and we witness greatness, we may decide, sorry, film like Michael Clayton, but not Michael Clayton because it's already locked in. You have to go sit down for Jared Hess's A Minecraft Movie, right? I think that is definitely likely. Is there anything you've got your sights on that's coming out later this year that you think could supplant something we've already selected? You don't have to say what it would supplant. Not yet, which is kind of depressing. Tough sledding so far in 2025. Yeah, but, you know, it's early. We tend to be surprised at this point by things that come out of especially Cannes, even though we're not going for some reason.

5:14and so and there are also there are a few directors who have films this year that still deserve a chance a slot on our list so I wonder whether the re-evaluation means that we can shuffle things around you're referring of course to Barry Levinson whose Alto Nights is coming shortly sure I think that that's more or less it right? I mean why are we doing this? because 25 is a nice round number. It's fun to do a project. But also, you know, we've been doing the show for eight years. It's been a long time. That's true. I think it's important to highlight that like this is from us, from you and me and from the show and to honor kind of the show and what we've been doing the last eight years.

6:01So it's very Hollywood focused. Yes. You know, I would like people are gonna... Not strictly. It's not strictly, But we are two children of the 90s who have always been obsessed with Hollywood and grew up reading Entertainment Weekly, unlike movie stars. And, you know, we do see things more widely, you especially. But, like, are there going to be as many—is this representative of the entirety of, like, world cinema in all its many languages and also genres? No, it is not. Like it's just not. It is personal to us. And so we are not trying to be definitive. We are not trying to be representative.

6:46We understand that there are both blind spots and just things we love. And we really did lean into things that we love. So that's how you make a list. But I just, I need people to repeat that to themselves over and over again. And to themselves. Don't share it with me. I think there's no making anyone happy when embarking on a project like this, except for ourselves. And we're happy with where we landed, sort of. I'm still kind of angst for it. Well, there's time. There's a whole year. There is. I have no complaints whatsoever about number 25. Well, except for, is it going to offend people that it's number 25?

7:23Well, it might even offend me, having just revisited the film. You and I, we saw each other this weekend. And the last week in movie going has, there have been some bright spots, but it's mostly been a slog. A little tough. And we were kind of, you know, stomping through the not fun stuff. And we shared that we were both saving Michael Clayton as a treat to watch on Sunday night as like the reward for all of this stuff. And so I did also then go home watching and I was like, 25, really? Like only? Are we sure? I found myself being like emotional by getting emotional about how good this film is and how much I love it I agree with you it just goes down like a cold glass of lemonade it is a very manageable tight beautifully executed thing let me give some details I'll try to give as much detail at the top before we begin a conversation this will be kind of a brief conversation for every movie that we do we're not attempting to do a rewatchables episode here It is more sort of an acknowledgement of why this movie works for us and why it belongs on this list relative to what movies have been for the past 25 or so years.

8:31So Michael Clayton comes out October 5th, 2007 in a fall in which many other great films come out, including A Country for Old Men, There Will Be Blood, a handful of others that are beloved, Zodiac. written and directed by Tony Gilroy who to this point has been a widely acclaimed screenwriter and also script fixer a ghost writer somebody who comes in and helps people solve problems in their screenplays has gone on to obviously incredible success directed a couple more movies is now probably best known as the creator of Andor the Star Wars series which is like the only good Star Wars thing that has come out since The Last Jedi probably um stars George Clooney Tom Wilkinson Tilda Swinton in an Academy Award winning performance Sidney Pollack as well a number of other great character actors strewn throughout the cast shot by the great Robert Elswit shot a lot of PTA movies one of the most gifted cinematographers of his time music by James Newton Howard this movie made 93 million dollars at the worldwide box office pretty good and it had it got seven Academy Award nominations including Best Picture Director Score and Screenplay and Best Actor for Clooney Best Supporting Actor for Wilkinson and Swinton's win.

9:41Why did this movie make the list? It ticks several sweet spots for us, including, and you were setting this up when you were talking about Tony Gilroy. We really like a writer's movie. We like people talking in rooms and talking really well. And this is one of the great screenwriters just absolutely seeing God. It is so perfectly plotted, just the ideas and structured. The dialogue is just like, you know, don't piss off a motivated stripper. Really, really important stuff. And it is sort of just a series of people, mostly men, talking in rooms or in alleys. but with such artistry and cynicism and just execution is spot on.

10:37So that really speaks to us and I feel like we had a lot of writers, writers who didn't quite make the list. So in some ways that can stand for this. The other thing is that it's like a movie star finally finding his moment in George Clooney who is one of the signature stars of our generation, but maybe not always the signature actor and definitely not the signature director. And this is his lights out moment. This is it. So I think in terms of Clooney, it's interesting because this comes in the aftermath of him winning an Academy Award for Siriana. And yet this is the unusual circumstance in which someone got their Oscar too soon rather than too late.

11:26Because this, to me, with maybe the exception of Danny Ocean, is his signature role. This is the best... Is it the best movie he's been associated with? Maybe Out of Sight is in that conversation. Maybe the Ocean's movies are in that conversation. Yeah, but also what he's doing in this movie is playing against everything that he's doing. Certainly in the Ocean's movie, even in Out of Sight to a degree, though there's more in common with Out of Sight, like the kind of down on your luck. But there's not an ounce of charm in this film. There is charisma. But like - He can't help but be magnetic. Yes.

12:06But I think, I don't think he smiles in this movie. Like maybe like a rueful smile that I don't really think counts, but sort of, you know, the George Clooney on the side of a tequila truck, which like, you know, knock it, But that is a big part of his persona. Totally. Is nowhere to be found. And so that he manages to pull something off and hold your attention without that sort of signature charm is what makes it so exciting. I think this is a very soulful performance from an actor who isn't always soulful, who I think was often accused of a little bit of smarm in the early stages of his stardom and who had a hard time kind of finding the right parts to break through.

12:47Should I be an action star? Should I be a genre guy? how do I get over the Doug Ross ER anxiety I think the thing that is cool about this part for him in particular is Clooney usually plays guys who have great luck like good fortune that's something that he kind of finds himself in which is somehow antithetical to great acting in a lot of ways you know like the fortunate soul is not somebody that it's harder to root for that person obviously he's a very handsome guy he's got this incredible charm in this movie he kind of does have everything else. He's incredibly intelligent. He's accomplished in his career.

13:23He has a family. He doesn't have exactly what he wants, but he has on paper the things that you would think you would want. But in the way that he has all of them, they're all without luck. His marriage is broken. His brother is an addict and has helped ruin his business. He's never really been able to transcend this skill that he has, this undeniable skill, the bag man skill, the fixer skill, which his superiors identify as making him a one of one. Yeah. But he knows kind of dooms him to a sort of grungy irrelevance in the wider world of lawyers. And so it is sort of against type for Clooney.

14:04Yeah. It's not really where he usually lives. And yet there are a few moments in the movie where, for example, he plays in an underground poker game. Sure. Which we see twice in the film. starts with a sort of flash forward and cuts backward. Which famously you don't really like except for this, which is perfect. This movie didn't invent it, but it did it in the way that is appropriate to me, which is that it shows you an event early in the movie, which is the explosion of his car, and gets you really thinking about what could happen and where we are in the story. I don't like it when it shows you something that doesn't really matter that much to the story.

14:37Anyhow, the poker game, for example, is like a place where if you saw a guy like George Clooney in a poker game like that, you'd be like, what the fuck is going on here? Like, why is there a guy this handsome, this clean cut, this suited? But we buy it in part because of the atmosphere that Gilroy creates. Characterization, plotting, and dialogue are all superlative in the movie. And so the vibe of the movie is sort of unmatched, I think, for your post-Sydney Lumet, Sidney Lumet-esque character study about a guy in New York trying to solve problems. So easy movie to love. Yeah. In addition to that, I think one other reason why it's here is that it has become a meme movie in a lot of ways.

15:22Yeah. You know, I've got my Michael Clayton hat here. The signs that go outside of people's homes. Yeah, yeah, yeah. It's like a grown-up cult classic. Yes, well put. And that sounds silly because as you enumerated at the beginning of the podcast, it was nominated for seven Academy Awards. It was not underappreciated in its time, but also it came out the same year as There Will Be Blood and No Country for Old Men. and, you know, two other movies about American men operating in a, you know, a capital, in a society. We live in a society. But operating in the rot of America. And so it has always, even though it's in no way an underdog movie, Like it has always felt a little underappreciated or like you're like in on something if you like it.

16:23Hence the yard signs, you know, in this house, we believe that Michael Clayton is an underappreciated. Like, is it underappreciated? I don't know. But it is sort of, you know, it's kind of like a code word or something. Like, you know, if you say to people like, I am Shiva, the guy to death. Like you either know that and you know what the person is referencing or you don't. I think it is probably the number one example of a movie from this century that we can point to and say, why don't they make them like this anymore? Because if you want to compare the other movies from that year, for example, like There Will Be Blood or No Country for Old Men, those are in many ways kind of forever movies and very difficult to pull off and very difficult to conceptualize.

17:07I don't want to take away from what Tony Gilroy put into this movie because he made a Swiss watch. But it's much smaller, much more grounded, much more achievable on its face than those big, big movies. And so this feels like if we can't have one as good as Michael Clayton, maybe three that are three quarters as good as Michael Clayton. It's something that we had gotten used to in the 90s and in the 80s and in the 70s. There's a long history of movies like this. And so it is something that I think is very easy to point to and say, this was the last time this kind of thing was great. And I like adult cult classic, grownups cult classic.

17:41That's a great way of framing it. All of that is true. I think if you got one movie half as good as this, you would feel really good. Because again, I think we're underestimating how hard it is to do what this movie does well. Is there a doubt, a false note in this movie? Like, is there a moment where you're like, nah, I'm not completely locked in. You aren't doing this exactly right. Is there a bad line of dialogue? Like, is there a bad performance? You texted me and you said every single supporting actor is absolutely lights out. I, last night, was thinking to myself, is this the greatest thing that Sidney Pollack ever did?

18:21Like, across all films made, produced, like, everything. It's a great question. I was watching a Sidney Pollack scene when I texted you. Obviously, Tom Wilkinson and Tilda Swinton have big, showy supporting parts. They have like old school Hollywood supporting star parts. They both got nominated. We understand why they're so great. To me, the magic of the movie is Sidney Pollack, Michael O 'Keefe, Ken Howard, Merritt Weaver, Dennis O 'Hare, these people who pop up, who are theater veterans, who show up in movies for one minute or three minutes at a time. Pollock, of course, a filmmaker who, I think to our generation specifically, emerged more strongly as an elite character actor than as the guy who made Out of Africa.

19:07Right. You know what I mean? Or like Three Days of the Condor or, you know, the way we were. Yeah, Tootsie, a number of incredible movies in his career. But he's this guy. He's the guy from Eyes Wide Shut. You know, in this movie, he plays Clayton's boss, a partner at the law firm, somebody who is overseeing in the case of this story a civil case against a U-North which is a kind of Monsanto-esque factory farming agribusiness and it turns out that their weed killer has been killing people in the middle of the country where it's being used most often and so there's this civil action against them and he's trying...

19:46The Polly character is really interesting because he's not a villain. The movie, it has hitmen. And they're not really the villains either. No. It has a CEO. He's not even really the villain. We know his business is very unethical. And we understand that this movie does have a kind of an ethical point of view. Yeah. But the villain is another lawyer, a general counsel for a big company who goes to extremes. Well, yeah, but even she is sort of the... I mean, she is the villain, but she is played by Tilda Swinton with a tremendous amount of sadness and weakness. Weakness is really. And she's like a pathetic person, like laying out her pantyhose.

20:33Like literally. Very physical performance in many ways. And again, another really, really playing against type. Um, Attilda Swinton manages to look ordinary in this movie. She's gained weight. Yeah. She's very sweaty. Yeah, I couldn't actually tell whether she gained weight or was wearing padding, but they do, you know, make a point of shooting her in unflattering corporate clothing. And much of her characterization is the character preparing both physically and, you know, performatively for whatever speech she is going to put out into the world. Which is, says a lot with a little. But yes, so she is the villain, but Swinton plays it.

21:19And I would even say the character is written like, there's not, what are you going to do? Like it's sort of, she's inherited these problems. Someone else has made the decisions for her. She doesn't really, she's not doing anything with conviction. That last line, you know, there's a great confrontation. And the way she screams, you want the money? It's just like someone so out of their depth the whole time. So she is the villain, but like the system, the larger world is really the villain. And everybody is, everybody, including Michael Clayton, is playing their part and like has some guilt in them and is, you know, and who within the film feels guilt about that and how much is sort of the closest that you get to heroes and villains.

22:12It is very gray. I wrote down it's a noir with no sex or crime, an imperfect hero who lives in the shadows. it's also a melodrama without any love Michael Clayton does not have a love interest he's divorced they don't introduce anyone in a kind of baggy side story to say oh well he's living for something he does have a son but even the way that Clooney interacts with the young actor who plays his son there is a kind of like harshness a flatness he has one moment where he really you know kind of semi-inspires him by telling him what he is not but they don't try to force you to love this character in any way which I think is very admirable and the sort of thing that in most movies kind of gets noted to death like we need to have a moment where we're really rooting for him right and even in the moment that they give us to root for him where we have this triumphant like yes he won yeah at the very end of the movie the camera just trails him all the way to his cab and him kind of considering reflecting thinking about what he's lost, who he is in this world, how he spent his life, how he's gotten himself entangled in all of these gross problems of the world.

23:26It's also kind of a samurai movie. Yeah, you put, this was a good observation. You know, a man alone, he's got his own code. He lives within a system that he has to abide by, but until he decides to break their rules to abide by his own rules, you can really see Gilroy using that framework or like like a Knight's Tale kind of framework here too. Very classical kind of writing and screen imagination that's going into it that I think just like makes me feel very seen. You know, these are like the kind of movies that I really, really like, but it doesn't do it in any kind of showy way. Like the filmmaking style is very simple and clean.

24:07You know, it's very intimate. We're really on top of the characters a lot of time. Like you said, it's mostly shot in rooms, a lot of singles going to guys faces there's that moment when Sidney Pollack's character and Michael LaCue's character and Michael Clayton are talking about his new contract and the$80 ,000 bonus it's like very tense very funny he's an asshole yeah it's so good I love that scene it's like there's nothing yeah you don't have to see that on the big screen to get it which is maybe a little different from a lot of the movies that we'll pick here today where a lot of them will be grand cinematic achievements yeah this is like this would have been jammed into a TV show now and it would have fucking sucked.

24:45True. For a number of reasons, including it wouldn't have, you know, it wouldn't be like built within an inch of its life. And I mean that in a perfect way. Like not a wasted moment. Everyone says the exact right thing. Like not a bad line delivery, not perfect. But if you turned this into some like grand, you know, camera like exercise, it would take away from what it actually is, which is people saying truths and not quite truths to each other in like exciting but depressing ways. There is like, there is like, there is a grittiness and like an actual literal grayness in palette to the film that is intentional and I think communicates kind of the darkness and the, And there's, you know, one great, like what I call the working girl shot of like Clooney alone in one tiny box in an office building where you can see all the other office buildings.

25:49So there is visual consideration. It's just like not getting in the way. No, you're totally right, though. The way that a lot of the film takes place at night when it isn't at night. There are no sunny days here. It's all overcast. It's a certain time of the year. That's all intentional. He's always in a black suit, never really in anything else. I think the film's legacy in addition to the meme stuff is fascinating because Tom Wilkinson's performance is a big part of the legacy because the other significant meme is the bad guys. Yeah. And I think this is an interesting complicated portrayal of mental health at a time when maybe we didn't talk about it in the same way that we do now where you know Michael characterizes him as a manic depressive, the Arthur character who is this wizardly lawyer who's been a trial lawyer for many years at this very Tony firm and is hugely relied upon to power through these big cases for the firm, but is also not well and medicated and has a kind of spiritual breaking point with this case.

27:00falls in love with a participant in the case, a young woman who's testifying, portrayed by Merritt Weaver. We see on video him having a kind of breakdown where he strips his clothes off, professes his love to her. We later see him at other times giving these kind of whirling dervish speeches. He's got this incredibly active mind. I mean, the movie opens with just voiceover of one of his, you know, great monologues that is also clearly an episode of sorts. And just set to really beautifully shot, chilling portraits of corporate conference rooms. So, and people walking down halls. Yeah. Does it remind you of anything?

27:41No, not at all. And the baguette moment, the meeting. Yeah. You know, it's a very funny thing to post on social media, but it's a very sad and hard and difficult scene. because, you know, Arthur clearly a mentor to Michael Clayton. Right. I had not really clocked this previously, but there's a moment when we're in Michael's office and the camera pans to a photo on his desk and it's Arthur and his son together. And you realize that these are really like, these people mean a lot to each other. Well, that scene when the, and I mean, this is just like perfect. This is why Gilroy is one of the great screenwriters, but the son is really into this like Game of Thrones-esque book.

28:26Yes. That he keeps trying to. Uh, yeah. Yeah. That he keeps trying to get his dad to read, but instead Arthur and the son end up on the phone. And the son is explaining this idea, like the ideas of this fantasy world to this person who is clearly going through like a real mental episode, but also like the themes are speaking to him. And it's, but they also have like some sort of emotional connection. It's, it's pretty devastating. Yeah, and Wilkinson is amazing in this movie. We shouldn't not have fun at the expense of the character, but the character is really a tragic figure. Yeah. And someone who, in theory, I think stands in for people who are truth-tellers, you know?

29:10And even though he's got this 30-year record of defending big corporations, ultimately he has this moment of realization as he gets clear of his medication, I guess. And I was trying to locate what the movie is really trying to say about that. Like, is it trying to say that if you are in this line of work, you need to delude yourself to kind of continue on and doing that kind of work. Is it actually his break is problematic and, you know, dangerous? And so he is just this sort of like Shakespearean fall from grace type. Like the movie is a little ambiguous about that. Yeah, intentionally. I don't think it's trying to give you an answer one way or the other of this is how you should feel about...

29:55I think now bipolar is the term for it. But again, it was 2007, so I'm not up on my psych book. Anyway, it is about, I think the tragedy is the point. And I think that it's a series of characters who are all confronted both with limitations or setbacks and also the opportunity to do something more right or less right. And how are they each negotiating it in their own way? And his is just like a deep tragedy. And even that scene, I mean, he's holding the baguettes. Again, when this movie has visual flourishes, it has visual flourishes. Like all time. but that scene itself the two actors just going at each other as Zach said last night when we were watching like top five movie scenes of the it is heartbreaking it is incisive it is I'm not the enemy well then who are you you know and it turns even for that character in a way that is a little scary and definitely sad so I don't know I think the ambiguity is the point the other thing that I wanted to note about the movie is like a lot of Gilroy's work, it's very interested in the kind of the intersection of big power and working class people.

31:25And Michael Clayton, whenever we get sucked out of the world of the law firm, he basically gets sucked into his family. So he's got this brother who's struggling with addiction who caused the flame out of his restaurant. He's got a brother-in-law who's a cop. He's got a sister-in-law. I think they're in Jersey, house in Jersey, or maybe is it upstate New York? I can't recall where they are. and he's the son of a cop too and when he's around his family everybody calls him Mickey and when he's in the office everybody calls him Michael these are very small choices is it not Long Island? it's not like Queens toward Long Island because I think at some point because his detective brother ends up helping him out in a couple places and they say I knew your brother out and let Queens I might have just missed it it might even be Long Island let's just say it's very familiar terrain as I watch the movie these are very familiar kinds of guys but I like this kind of this world and that world and you know Michael in theory being the one who got out and got away from the working class lifestyle but is in fact more in the shit than anybody who sees the worst possible things you know the famous sequence early in the film when he's summoned to Dennis O 'Hare's home where he and Julie he's just struck a man in the street while driving it was a great sequence for a variety of reasons I love it.