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The Heist Movie Trophies

To commemorate the release of ‘The Hurricane Heist,’ two experts on cinematic robberies dole out awards for the best heist movie one-liner, mask, gadget, and more

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Spoiler alert

Shea Serrano: JAAAAAAAAAAAAAAAAAAAAAAAAAAAASON! A NEW HEIST MOVIE COMES OUT FRIDAY! IT’S CALLED THE HURRICANE HEIST! JASON, GET READY FOR THIS, BECAUSE IT’S NOT JUST A REGULAR HEIST MOVIE ...

Jason Concepcion: THAT’S CORRECT!

Shea: IT’S A HEIST MOVIE …

Jason: IT IS!

Shea: THAT HAPPENS …

Jason: WHAT ARE THE WEATHER CONDITIONS, MY GUY???? SHOW ME THAT DOPPLER RADAR!!!!!!

Shea: DURING A HURRICANE!!!!!!!!!!!!!!!!!!!

Shea: It’s going to be so, so, so bad and I honestly can’t wait to watch it. Jason, do you like heist movies?

Jason: Shea, I love heist movies. I would never rob a bank. I would never break into a top-secret facility to steal a list of spies. I would describe my driving style as “cautious,” so I would never engage in a high-speed chase across an urban cityscape using a custom-built vehicle. I can’t hack a computer. Pretending to be a different person and perhaps wearing a mask and using some gadget to alter my voice in order to get around security sounds thrilling but also super stressful. All those activities sound stressful, in fact.

Shea: I like that this heist movie conversation has already just turned into a list of things you couldn’t or wouldn’t do.

Jason: But I want to do them. I just don’t want to go to jail or get banished to some covert black site or get murdered by thick-necked organized-crime thugs. That doesn’t mean I wouldn’t love to rob a bank, though, Shea! I mean, who hasn’t walked into a bank and thought, “Hey, wouldn’t it be great to walk out of here with a sack of free money?” That’s where the heist movie comes in. That’s why I love heist movies.

Shea: Wish fulfillment is definitely a good reason to love heist movies. Do you love all of the parts of heist movies or only some of the parts of heist movies?

Jason: I love everything. But to me, in order to be considered a true heist film, three crucial elements must be present. I call it T.P.S.—assembling the Team, Planning the caper, and taking down the Score. You have to have the three parts. Those are essential. Everything else is basically a flourish.

Shea: I love all the parts of heist movies. I love the thing they do where we get to meet all the different members of the heist crew. I love the thing they do where someone gets pulled back into the game to do “one last job” or when someone describes a potential heist as impossible. I love the thing they do where, after it looks like a plan has begun to fall apart, we find out at the very end that that’s exactly what was supposed to happen. I love the thing they do where they plot out how the heist is going to happen (my personal favorite version of this is when they do it in a diner booth and use condiments and other tablewares to represent different things). I love the thing they do where some tiny thing from the beginning of the movie turns out to be a very meaningful thing later in the movie. I love the double cross. I love the reverse double cross. I love the getaway scene. I love the cop who is always half a step behind. I love all of it. What am I missing?

Jason: Oh man, I love the tiny meaningful thing! The Lookout has one of my favorites.

Shea: That’s a solid movie. I really like the tiny meaningful thing in The Town, and of course I’m talking about how Claire (Rebecca Hall) tells Doug (Ben Affleck) the story early in the movie about how sunny days always remind her of her dead brother because he died on a sunny day and then the movie ends with her in her apartment with the FBI, and she’s on the phone with Doug and tells him he should come over, that it’ll be one of her “sunny days.”

Jason: You’re missing two scenes.

Shea: Which ones?

Jason: The one when they break up the score after the heist and the one where the heist crew, now flush with cash, begins making a ton of mistakes. Draping significant others in mink coats and diamonds, rolling up to the neighborhood dive in a sports car, that sort of thing. I call that The Lufthansa (after the heist in Goodfellas) and the result is always ruin and murder. But, of course, I love that stuff too!

Shea: Let’s do a thing to celebrate all this stuff, yeah? Let’s give out some trophies for different heist movie things, words, and moments.

Jason: I’m in. Are there any rules we need to have in place beforehand? There have to be rules. There are always rules.

Shea: Yes, but they’re easy. The four rules:

  1. The Point Break Rule: For the purposes of this article, we’re only going to consider heist movies that happened after 1991. You can circumvent this rule by opting to choose a remake of a movie (the original Ocean’s 11 came out in 1960, the remake came out in 2001; the original The Italian Job came out in 1969, the remake came out in 2003; the original The Thomas Crown Affair came out in 1968, the remake came out in 1999; etc.), but that’s the only way around it. That means we’re losing iconic heist films like Dog Day Afternoon (1975), A Fish Called Wanda (1988), The Thief (1981), The Sting (1973), and so many more.
  2. The Heat Rule: Conversations like these are often very Heat-heavy. I get that (Heat is obviously incredible). But I don’t want it to happen here. So, with apologies to Vincent, Neil, and Chris, nobody is allowed to offer up Heat to win any of the trophies we’re giving out.
  3. The Joker Rule: Any movie or character from a movie or whatever that you’d like to talk about here has to come from an actual heist movie, which is very different than a movie in which a heist happens to take place. For example, the opening scene of The Dark Knight is a bank robbery, and a bank robbery is absolutely a heist, but nobody would ever categorize The Dark Knight as a “heist movie.” So, with the exception of the one trophy we have set aside for moments exactly like this, those kinds of movies (and characters and scenes from those movies) are out.
  4. The Top 5 Rule: This one is more of a general guideline than an actual rule, but I vote that we stay away from regular, normal categories that happen in these kinds of lists. What I mean is, I don’t want to do a bunch of stuff like The Trophy for the Best Heist Movie Ever or whatever. Let’s try to hit things that either (a) haven’t been done before, or (b) haven’t been done to death yet.

So those are the rules. Everything else is fair game.

Jason: I’m giving Heat the Trophy for Best Heist Movie That We Aren’t Mentioning.

Shea: Let’s do 11 trophies ...

1. The Trophy for the Best One-Liner in a Heist Movie

Shea: Did you see the movie Heist? I don’t mean the one that came out in 2015 that had Robert De Niro in it (which was really bad). (The big twist in it was a pregnant woman on a bus turned out to not actually be a pregnant woman; she was a plant and they used her belly to hide stolen money in, which is a version of a hustle that has been happening in Walmarts and Targets across America for years.) I mean the Heist that came out in 2001 that starred Gene Hackman. In it, Hackman plays Joe Moore, leader of a gang of expert thieves, and as the leader of a gang of expert thieves, he has to be the smartest, most forward-thinking, most prepared person in every room that he walks into. And those rooms, given the company he keeps, are often already filled with other people who consider themselves the smartest, most forward-thinking, most prepared person in every room they walk into.

Despite the movie not being all that great, there are three very good lines in it. The third-best line is when Danny DeVito (the movie’s main antagonist) is on the phone and he yells, “Everybody needs money! That’s why they call it ‘money.’”

The second-best line is when Delroy Lindo (he’s Hackman’s main crime partner) is sitting in a car next to a jumpy soul and he mentions how if he’s feeling nervous then maybe he should pray a little. The jumpy soul sort of laughs him off, and so Lindo responds by telling him a story about how one time he was working with a guy who would carry a Bible around in his pocket in front of his heart. Lindo says that everyone made fun of the guy for it, but one job ended in a firefight and the Bible stopped a bullet that would’ve destroyed the guy’s heart. The jumpy soul, moved by the story, finally begins to pay attention. “No shit?” he asks earnestly. Lindo pauses for a moment, then says, “And had he had another Bible in front of his face … that man would be alive today.”

And the first-best line—which is also the best one-liner that has ever happened in a heist movie—happens when a person impressed by the way things have turned out says to Hackman’s Joe Moore, “Nothing like a good plan, Joe.” Joe, without missing a step, says, “I wouldn’t tie my shoes without a backup plan.” That single line, I would argue, perfectly encapsulates the most appealing character trait (a confident coolness rooted in intellectual superiority) of the most appealing type of character in a heist movie (The Leader), which is why it’s the A1 pick here.

Jason: That line is incredible. Heist is great because I think there are like 15 double crosses in that movie. Like, Joe and Jimmy (Sam Rockwell) double-cross each other so much that they basically end up where they started except Jimmy’s with Fran, Joe’s wife.

Shea: I feel like two things should be mentioned here: (1) Sam Rockwell has that very specific kind of face where, as soon as you see him in a movie, you go, “OK, yeah, this guy is definitely gonna try to be up to some shit.” The instant he’s introduced in Heist, it’s clear that he’s on the hunt for a double cross. (2) This movie came out in November 2001. Four months earlier, a different heist movie called The Score came out. It starred Robert De Niro and Edward Norton. The Score was better than Heist in basically every way possible (it was more nuanced; the characters were cooler; the reverse double cross was way more unexpected; the reveal of the reverse double cross was more energetic). And still, there’s no way around not giving the following trophy to one of its principal characters …

2. The Trophy for the Worst Execution of a Double Cross in a Heist Movie

Shea: Let me be clear here. I’m not saying that the way that the double cross was written into The Score was bad, because it wasn’t. It was very serviceable and fun. What I’m saying is that the person who executed the double cross did so in the clumsiest, most short-sighted way possible.

A recap: Edward Norton plays a semi-slimy young thief named Jack Teller. He partners up with Nick Wells, a glacier-cool old safe cracker played by Robert De Niro, to steal a sceptre worth millions of dollars from a customs house in Canada. Teller worked the hustle from the inside—he got a job there as a nighttime janitor weeks beforehand to not only case the joint, but also so that he could disable the alarms and reroute the cameras while Wells was breaking in; also, it should probably be mentioned that Teller was pretending to be mentally disabled while he worked as the nighttime janitor, which I guess he did to make the other people who worked there less suspicious that he was going to rob the place. After Wells breaks into the safe and steals the sceptre, Teller holds him up at gunpoint and takes it. He tells Wells that he didn’t like how he disrespected him, and that he was taking the sceptre (and the money that would come with it) for himself.

The security guards finally realize they’re being robbed, the alarms get sounded, and then the police come busting in. Teller, now pretending again to be mentally disabled, walks out of the front door during the mayhem and then fucking books it to catch a bus out of town. THE PROBLEM WITH THAT, and what Wells had tried to explain to him beforehand and then reinforces to him a few minutes after they escape when they talk on the phone, was that as soon as Teller did that, everyone knew he was in on the scam. That’s why the double cross here was so bad. Because not only did it not work (Wells suspected that Teller was going to try it, and so he had a fake sceptre wrapped up that he gave to him), but it also exposed him as one of the thieves.

Jason: Doesn’t he also reveal himself to be one of the thieves to that old man he was working with?

Shea: Yes! He was paired up to work with an old man and they had become friends over the weeks that they’d worked together. The old man walked into the room where Wells was hacking into the computer system at the customs house as he was doing it, but Wells could’ve easily just bopped him on the back of the head and knocked him out or tied him up or something without letting him see his face. Instead, he made it a point to let the old man know that he’d been playing him the whole time. Ultimately, Teller was just too insecure to be a top-tier criminal.

3. The Trophy for the Best Heist in a Non-Heist Movie

Jason: This is easy—Ethan Hunt (Tom Cruise) and his crew of outlaw spies stealing the NOC list from CIA headquarters in Mission: Impossible (1996). The list is kept on a computer which is locked in a vault that can only be accessed by voice identification, a six-digit access code, retinal scan, and a key card (which Ethan and his team don’t have), and that is protected by an alarm triggered by any sound above a whisper, a sensor that detects heat which can be triggered by an unauthorized person’s body heat, and a pressure sensor on the floor.

Ethan and his team take down the list by:

  • Faking a fire alarm and infiltrating the building dressed as first responders.
  • Getting into the lunchroom in disguise, putting a tracking device on the CIA analyst allowed to access the room, and slipping a drug into his drink that makes him violently ill.
  • Dropping down 30 feet through an air vent on a rope to hack the computer while trying not to sweat or touch the floor or have any sweat touch the floor or make any sound at all.
  • Killing a rat by biting it.
  • Downloading the list.
  • Escaping in the fire trucks.

It’s actually pretty wild to think they’ve now made six of these movies! Mission: Impossible is criticized for being confusing—which it isn’t except for the [SPOILER] part where Ethan’s mentor Jim (Jon Voight), who you think is dead, turns out to be alive and is in fact the mastermind behind the convoluted plan which framed Ethan for the murder of his own team in Prague at the beginning of the movie. So, I don’t think there’s a Mission: Impossible film franchise without the CIA heist scene.

Shea: This is a really good pick, but I’m saying that mostly because this is the Mission: Impossible where Ethan Hunt has the best haircut, because best haircuts are wildly important to me. (If I need to give an answer here, then I’d probably go with the Dunkaccino scene from 2011’s Jack and Jill. It just stole way too much of Al Pacino’s integrity.)

4. The Trophy for the Best Setting for a Heist in a Heist Movie

Shea: Is it a bank? It has to be a bank, right? I don’t want to overthink this category.

Jason: Oh hell yeah. A bank is a (sorry) rich text for a heist. As I said above, who hasn’t thought of robbing a bank? That said ...

5. The Trophy for the Best Gadget or Technology Used in a Heist Movie

Jason: The Inception dream-sharing technology! I’m confident this one cannot be topped. We’re talking about a reverse heist (planting a thing instead of stealing one) inside of a dream and none of that would be possible without the dream tech. Without that, there is no movie! And that shared-dream twist makes Inception’s T.P.S. elements feel totally new. (Also, shouts to Christopher Nolan for making a movie that depends heavily on technology in which you barely see the technology.) The Score portion, in particular, is a reverse heist inside of a heist inside of a heist. And the stakes aren’t some pedestrian thing like prison. If Dom and his crew fail, they might just spend all of eternity trapped in their own crumbling subconscious with no way out except dream-suicide.

Shea: Please let me say two things. First, it feels a lot like you cheated here, but yes, you’re correct. This one is unbeatable. And second, I’m also awarding this movie the sixth trophy of this column. I’m giving it The Trophy for the Best “I Think I Understand This Movie But Maybe Not” Feeling After Watching It. I’ve seen Inception probably a good 10 times, and still I’m not all the way certain I know exactly what happened in it. (And it would be great if you didn’t send me a bunch of diagrams drawn out that are supposed to explain it, because that’s always what happens when I say I didn’t really understand the movie.) (And just to be all the way, totally, completely clear, it’s not that I don’t understand the whole movie—that part is easy—it’s that I don’t understand the ending. Was he inside of a dream or was he in the real world? If you have a firm answer for that, then I would very much like to receive it.)

Jason: I have no answer! The ending of this movie is something that will bother me forever. I NEED TO KNOW IF DOM IS IN THE REAL WORLD OR NOT. Christopher Nolan cutting away from the totem when it’s about to reveal whether Dom is in a dream is the one time I’ve wanted to fight a film director. And I love that movie.

7. The Trophy for the Most Clever Twist in a Heist Movie

Shea: There are 100 different ways to play this one, but here’s what I’m looking for in a good twist in a heist movie. I need for it to do three things. It has to:

  1. Not be a double cross. Don’t get me wrong. I don’t mean to say that I don’t like a good double cross, because I LOVE a good double cross. It’s just that the double cross can’t be the only big twist in the movie. It needs to be something extra.
  2. Be entirely unexpected WHILE ALSO making sense. This is way harder to pull off than you’d expect.
  3. Be a called shot. The person doing it has to tip his or her hand in a way that is innocuous during your first watch through, but then becomes a big, bright, flashing sign every time after that.

With those things in mind, the trophy for the most clever twist in a heist movie goes to Clive Owen’s Dalton Russell from Inside Man (2006). In Inside Man, Russell and his robber teammates rob a bank owned by a war criminal. During the process, he talks to a hostage negotiator on the phone (Detective Keith Frazier, played by Denzel Washington). As they’re talking, Russell tells Frazier that he’s going to walk out of the front door when he’s “good and ready.” A bunch of other things happen, and more things happen, and then more things happen, and then finally the movie ends with this scene:

If you’ve not seen Inside Man and need an explanation: While the robbery was taking place (it happened over several hours of a standoff with the police), the heist crew built a false wall in a storage room and Russell hung out in there for a week until the police presence evaporated. When everything was clear, he climbed out, put on a hat and glasses, and then walked out the front door just like he said he would. (He even purposely bumps into Detective Frazier in the lobby on the way out, but Frazier doesn’t know it’s him because he never saw his face.) It was a brilliant play, and one that the movie slyly worked at setting up for its entirety.

Let me ask you a bonus question since we’re here, Jason. Is Jodie Foster’s Madeleine White secretly the best character in the movie? Because the more I watch it, the more it starts to feel that way. Clive is at his most Clive Owen-y. And Denzel is fantastic, as usual. But, I mean, she has such a strong gravity in this movie. It’s my second-favorite Jodie Foster performance, behind only her performance as Clarice Starling in The Silence of the Lambs, and slightly ahead of her performance as Kyle Pratt in Flightplan. (And I know Flightplan isn’t a super good movie, but that doesn’t mean that she’s not super good in it.)

Jason: I love Inside Man. I would just like to point out, though, that the heist plan—a hostage situation acting as cover for a robbery—is nearly identical to the plan in Quick Change, the 1990 Bill Murray film in which he dresses as a clown in order to take down a bank.

OK, that said, I disagree. For me it’s the moment in Reservoir Dogs when you realize that Tim Roth’s Mr. Orange IS ACTUALLY AN UNDERCOVER POLICE OFFICER. Also—Reservoir Dogs is one of the most rewatchable heist pictures of all time, and you never see the actual heist! This is the exception to the T.P.S. rule! There’s no score! It’s just T.P. The last two-thirds of the film is an extended Lufthansa culminating in an iconic Mexican standoff and shootout. See: Lufthansas always end in ruin and death!

Here’s how the twist plays out: A gang of anonymous criminals, all going by names based on colors, is assembled in order to take down a jewelry store. The caper goes sideways when cops appear seemingly out of nowhere and surround the store. In the course of the escape, Mr. Orange is shot in the stomach. Mr. White, an avuncular mentor type, and Mr. Pink, a classic hothead, bring Orange back to the gang’s hideout to bleed out on the floor. Clearly, because of the way the cops seemed to be one step ahead of the gang, someone snitched to the cops.

Enter Mr. Blonde, an ice-cold psychopathic murderer. He arrives back at the hideout with a tied-up police officer in the trunk of his car. White, Pink, and Blonde proceed to work the poor guy over. Then White and Pink go to ditch the getaway cars, leaving Mr. Blonde in control. He proceeds to torture the policeman, first cutting off his ear, then dousing him with gasoline. He’s about to light him up when—bang, bang, bang, bang—Mr. Orange, drenched in blood, shoots him, revealing that he, in fact, is the mole.

8. The Trophy for the Best Mask in a Heist Movie

Jason: The full clown costume from Quick Change!

Shea: No, sir. Not only is this in violation of the Point Break rule we laid out earlier, it’s also in violation of the actual ex-presidents masks from Point Break, which are the greatest heist movie masks of all time. It goes:

  • First place: The ex-presidents masks from Point Break.
  • Second place: The nun masks from The Town.
  • Third place: The clear masks from Set It Off.
  • Fourth place: That gross-looking melty-face rubber mask from The Robber.
  • Fifth place: The face-paint masks from Dead Presidents. (These are honestly probably cooler than the masks in third and fourth place here, but they’re far too impractical to finish any higher than fifth place.)

Jason: OK. I revise my choice. I’m going with Julia Roberts playing Tess Ocean playing Julia Roberts in Ocean’s 12. It’s more of a metaphorical disguise, not a mask. And I’m not saying it should win the trophy. I just think it’s a super weird thing that happened in a heist movie.

9. The Trophy for the Second Most Important Member of a Heist Crew (Assuming the Leader Is the Most Important)

Shea: My heart is telling me that the Getaway Driver is the second most important member of a heist crew, but I think that’s only because drivers have been so romanticized this past decade and a half. When I focus all of my energies and brainpower into being as objective as possible about this particular category, it’s not the Getaway Driver who I come up with as the second most important member of the heist crew. Because do you know who it is? It’s the Unpredictable One.

Nearly every heist crew from nearly every heist movie has the Unpredictable One in it. And the Unpredictable One is important for any number of reasons, including but not limited to:

  1. Being the muscle. There’s always a moment when someone in the bank (or whatever it is that’s being robbed) bucks back some. And when that happens, you need a person who’s going to react in such a big, violent, intimidating way that everybody else in there falls in line.
  2. Creating tension. It’s always interesting when someone in the heist crew starts butting heads with someone else in the heist crew. It makes everything feel more volatile, more precarious, more intense. And that usually leads to ...
  3. Causing a mess. You know what part of the heist movie I tend to enjoy? When things start to unravel, or go bad, or fall apart. And whenever that happens, it’s typically because the Unpredictable One has done something unpredictable.

Now, I know that not EVERY heist movie crew has the Unpredictable One—in fact, the best argument against the Unpredictable One as the pick here is that there wasn’t an Unpredictable One in the Ocean’s 11 franchise, and the Ocean’s 11 franchise is the overall most compelling, most well-constructed heist movie crew. THAT BEING SAID, I think this kind of character shows up enough elsewhere to make him or her undeniable. (My no. 1 favorite Unpredictable One in all of the heist movies is Queen Latifah’s Cleo Sims from 1996’s Set It Off, a wildly underappreciated movie.)

Jason: I can’t argue with this. Heist movies would be boring without the Unpredictable One causing a ruckus and providing comic relief. You know who’s an underrated Unpredictable One? K-2SO from Rogue One: A Star Wars Story.

10. The Trophy for the Best Wahlbergian Performance in a Heist Movie

Shea: Oh, hey. What’s up Mark Wahlberg in The Italian Job?

Jason: That’s perfect. Honorable mention for the cocaine dealer rip scene in Boogie Nights, which wins the combined Trophy for Best Wahlbergian Performance in a Heist in a Non-Heist Movie.

11. The Trophy for the Most Conflicting Death Scene in a Heist Movie

Shea: I really, really, really love Hell or High Water (2016), which somehow manages to feel like both a contemporary heist movie and also a traditional Western. The characters—Jeff Bridges as a weathered piece of saddle leather who’s really a Texas Ranger named Marcus Hamilton; Gil Birmingham as his bullied-but-beloved partner; Chris Pine as the quiet and handsome Toby Howard; and Ben Foster as his wild ex-con brother Tanner Howard—are all wonderful and fully fleshed out. The setting (the dusty expanse of West Texas) is beautiful. And the pacing (deliberate, but with a taut energy) is confident. It’s just an all-in-all great movie, and it’s capped off by a hillside shootout that leaves Tanner dead, leaned up against his rifle after having the top piece of his head shot off by Marcus from some hundred yards away.

There was really no way around the death—not only did they have Tanner pinned in, and not only had we just watched Tanner commit murder himself, but also the movie needed for him to die for you to know that Toby, Hell or High Water’s true center, and his estranged wife and children were going to be free from a life of worry—but it still felt … I don’t know. Is “weird” the right word? Tanner was obviously a bad person, but there were also whispers that he had goodness in his bones, it seemed. (This is a thing Ben Foster does exceptionally well in movies. He’s so good at appearing manic and wild while also giving his characters juuuuuuust enough depth that you begin to insert backstories into your brain to excuse his actions.) So even though it was clear that he had to die, it was still hard to watch.

Even now, after having seen Hell or High Water many times, I don’t watch that part. I just skip right past to the end when Toby and Marcus face off on the porch, Marcus suspecting that Toby was also in on the robberies, Toby knowing that Marcus killed his brother but also knowing that there’s no way Marcus will ever be able to tie him to the robberies and he’ll get away with if he just does nothing and says nothing. This is the pick for me. Do you have a different one?

Jason: Kind of. I have always found it extremely weird that Ben Affleck’s Doug, the leader of a bank robbery crew from Southie, is unambiguously the hero of The Town despite the fact that, like, he and his gang maybeeeeeeeeeeeeeee kill a bunch of cops during the climactic shootout at Fenway Park??? I mean, we never see cops die on screen. But my dudes unleash several thousand full-auto clips in the direction of dozens of police officers. It would be extremely lucky if a few weren’t clipped. That’s all. I always found that strange.