Jeremy’s Tophunder №43: Rounders

8 min readJun 22, 2020

As opening lines go, Rounders has one of the best of any movie on my list:

Listen, here’s the thing: If you can’t spot the sucker in your first half-hour at the table, then you are the sucker.

I’m not exactly a poker whiz, but I’ve played more poker in my life than most people I know. I’ve played at casinos a few times and not embarrassed myself, and I tend to avoid playing for any real stakes with friends, because I feel bad about taking their money. What I can tell you is that this sentiment is true. I’ve been on both ends of it. I’ve felt like a fish out of water playing at casinos (and I suppose I got a little lucky to walk away with about as much money as I sat down with), and I’ve played home games where I know exactly who is going to lose the $40 they brought.

Rounders came out at just about the perfect time. Poker didn’t really explode into the popular consciousness until the early 2000’s (Chris Moneymaker winning the 2003 World Series of Poker in his first ever live poker tournament resulted in an explosion in the popularity of online poker), but the intrigue of underground high-stakes poker had been around for years. Rounders dove into that world, and while it didn’t become the cult hit it is today until after the poker boom, you could probably argue that it helped facilitate it, with a number of poker pros of that era citing it as an inspiration.

It caught two stars in their absolute prime — Matt Damon was fresh off Good Will Hunting and Saving Private Ryan, and Edward Norton was sandwiched in between American History X and Fight Club. You really couldn’t have asked for a better duo of 20-something actors in 1998. Damon, seemingly as always, is perfect as the pure-hearted kid just trying to help out a friend and be great at poker, and Norton is absolutely spectacular as the smarmy ex-con who deals from the bottom of the deck and generally causes mayhem because he’s the only one that can’t see how obnoxious he is.

The beauty of the movie comes from the supporting cast, though. John Malkovich, as Russian mobster Teddy KGB, submits one of the most spectacular and ridiculously over-acted performances of all-time, and almost certainly the most spectacular and ridiculously over-acted performance from any movie on my list. Like, there’s chewing on the scenery, and then there’s making a seven-course meal out of it.

Like, what is that accent? There are only two possibilities here. Either (a) nobody on the set told him to tone it down a bit, which I would be very thankful for, because this performance is just as funny as anyone from any comedy movie on my list, or (b) he started off even more over the top than this, and what we get in the movie is Malkovich actively holding himself back, which is somehow even funnier. Malkovich’s performance is one that I think about a lot. I genuinely don’t know whether to classify it as good acting or bad acting. It’s so far beyond the boundaries of normal acting choices that I think it honestly might transcend any traditional definition of what makes a performance good or bad. I want to say that it’s bad acting on the part of Malkovich, but if it is, it’s very obviously intentional. So is bad acting still bad when you’re actively trying to be… whatever the hell Malkovich was in this movie? I really don’t know. I have spent countless hours thinking about this over the last however many years since I’ve seen this movie, and today, I’m no closer to a coherent answer than I was then.

As for the rest of the cast, John Turturro is great in just a handful of scenes, Michael Rispoli is great, and Martin Landau is also great as Matt Damon’s law school professor. Even Gretchen Mol, while playing possibly the most infuriating wet blanket girlfriend in movie history, still manages to play the part well. It’s a surprisingly deep cast for such a small movie, and while I can’t call it well-acted across the board (again, I just can’t make heads or tails of John Malkovich’s performance), I’d say the acting is good enough, and the writing is good enough, that it has a disproportionate amount of memorable characters for a movie that’s ostensibly about Matt Damon playing cards.

If there’s anything in the movie that I find a bit annoying at this point, it’s probably the amount of voice-over used to explain the ins and outs of poker, and the intricacies of certain hands as they’re being played. But I know that it’s an unfair criticism, for a few reasons. First and foremost, though, it’s my knowledge of poker (and seeing the movie 40 or 50 times) that makes those voice-overs unnecessary. But for the average viewer, they need that extra explanation for those scenes (and the movie in general) to make sense. It’s kind of the same way that I get a little annoyed at a movie like Moneyball — I know more about baseball (and baseball statistics) than most people, so when a movie “dumbs down” their subject matter to be accessible to a wider audience, it comes off as overly simplistic to people who already knew what was going on.

On top of that, though, are a few moments that feel just a little bit forced. For instance, in the movie’s opening scene, Matt Damon calls time immediately after a big bet from Teddy KGB. I don’t think I’ve ever seen that happen before. In the movie, Mike McD is trying to appear shaken by a big bet, because he has a monster hand and he’s trying to get paid off. But either Matt Damon’s performance (of a poker player) or Mike McD’s performance (of a fake bluff) falls flat. I’m just not sure which. Then at the end of the movie, Mike McD’s huge win over Teddy KGB is just a little off. If KGB is putting Mike on a dead hand, the last huge bet he makes is objectively wrong. Here are the potential outcomes:

The opposing player calls your huge bet with a dead hand (extremely unlikely, bordering on insane)
The opposing player calls your huge bet with a live hand (meaning you put them on the wrong hand and you’ve likely lost the hand)
The opposing player folds (so your enormous bet is irrelevant)

And again, we know that KGB thinks that Mike has a dead hand, because he’s talking about the hand as the cards come out. We all know how KGB is reading the hand. Shoving all-in seems to have no real upside — it makes more sense to put another mid-sized bet, hopefully one small enough that the opposing player is priced into calling. The explanations for KGB’s bets here are either that he’s a really bad poker player (which openly contradicts how the movie establishes his character), or that the scene is constructed in a wildly unrealistic way because the movie needed an exciting ending. Neither of those explanations is particularly satisfying.

But again, these criticisms are stemming from an underlying knowledge of poker that most of the audience doesn’t have. After all, it -is- a Hollywood movie, not a documentary about poker. The poker scenes are just realistic enough that they work, regardless of your knowledge of poker. The only reasons a few of them bother me is because I’ve gone so far down the rabbit hole thinking about how I would have played these hands after watching the movie several dozen times.

Rounders, almost by default, is probably the best poker movie ever. It handles poker far, far better than Casino Royale does (the odds of four consecutive players having a flush, a full house, a better full house, and then a straight flush is roughly 1 in 150 million), and there really aren’t too many other movies where poker is a central theme (Molly’s Game is the only other one that comes to mind quickly). Rounders just seems to capture the underground poker culture in a way that movies usually fall short in. It probably helps that screenwriters Brian Koppelman and David Levien played a lot of poker in New York in the early and mid-90s. The story is great (albeit predictable), and, like most great sports movies, the sports scenes are just barely realistic enough that I don’t get mad. Unlike most sports movies, though, the protagonist actually turns out to be far less interesting than the supporting characters. If anything, that’s the lasting legacy of Rounders for me. Worm, Teddy KGB, Grama, Knish, and Petrovsky are all great characters who submit great scenes, and ultimately, kind of steal the movie out from underneath Matt Damon, which seemingly has never happened before or since. I still have one more Matt Damon movie to get to before this project finishes out, but Rounders will always be one of my favorites.

(For a refresher on the project, I introduced it in a Facebook Post on Day 1)

Here’s our progress on the list so far:

2. A Few Good Men

3. The Social Network

4. Dazed and Confused

5. The Shawshank Redemption

6. The Fugitive

7. The Dark Knight

8. The Departed

9. Saving Private Ryan

10. Inglourious Basterds

11. The Big Short