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Craig Gillespie On ‘Dumb Money’ And Why He Loves An Outsider

Craig Gillespie is an enigma, an opinion I shared with him during this interview. It’s hard to find a through line through his films – narrative, style, or genre – which does see to leave a lot of critics not knowing quite what to do with him. He’s hard to define, in a business that loves defining people. When I bring this up to Gillespie he starts laughing, because he knows it’s true. A hopelessly sweet movie like Lars and the Real Girl doesn’t have a lot in common with, say, the needle-drop rage in I, Tonya or his gritty, stylistic take on a Disney villain with Cruella.

His latest is Dumb Money (which just premiered at the Toronto International Film Festival and is opening limited this weekend), as Gillespie tackles a full-on ensemble movie about how GameStop became the battle line between ordinary people looking to make some money and the financial institutions hell-bent on making sure that doesn’t happen. Keith Gill (Paul Dano) is a little-known YouTube investor who loves GameStop stock partially because he feels it is undervalued because of the amount of financial institutions shorting it, and partially just out of his nostalgia for GameStop. Eventually, his recommendation catches on, becoming a movement against the banks that were shorting the stocks. Now, on paper, Keith is a millionaire as his wife (Shailene Woodley) and brother (Pete Davidson) wonder if he has a plan at all.

Meanwhile, we circle through a number of investors (America Ferrera, Anthony Ramos, Myha’la Herrold) and their thought processes on how long to stay in. We meet the financial titans losing hundreds of millions a day (Seth Rogen, Vincent D’Onofrio, Nick Offerman). And, of course, the two schmucks (Sebastian Stan, Rushi Kota) who founded the Robin Hood app and find themselves way in over their heads, finally leading to the day they take away the option to buy GameStop, which caused the stock to tank and signaled to the world, oh, right, this truly is rigged.

Ahead, Gillespie takes us through why he was very determined to be as faithful to the actual story as possible, and explains how Dane DeHaan wound up in this movie as a GameStop manager with a rat tail. And he comes up with a convenient through-line for his movies. He says it was never intentional, but when you look back at his movies, he does love an outsider.

(I was supposed to speak to Gillespie in Toronto, but we had to reschedule to Zoom because a day before I was supposed to leave for the festival I tested positive for COVID. Something that seemed quite obvious to Gillespie once I tried to speak, as I was still pretty sick. Then, immediately after this, went back to bed.)

Craig Gillespie: Hey there, Mike. How you doing?

It hasn’t been the best week…

Do you have COVID?

Yeah, I do. I was supposed to go to Toronto.

Just to empathize, my family was coming to Toronto with me. My one son, not the son that was involved in this story, but the other son that lives with his girlfriend, they flew in the night before us, on the red eye. He didn’t feel great the next morning, she tested positive. They had to miss the whole premiere. They flew to Toronto and missed it.

I wanted to see it again in Toronto with that crowd because I knew it would play well, and apparently it did. I’m sad I missed it but I’m glad you got to experience that.

Yes, I did. I was very happy I got to experience it.

I’m just going to go say, I bet it was more important that you were there than I was there.

[Laughs] I was sitting there and being like, “Where’s Mike?”

Last time I spoke to you was for Cruella. When the GameStop stuff was happening, were you finishing that up?

I was definitely on the tail end of that, and was starting to gear up for another film that I was developing. I was living it with my son and in the thick of COVID. It was this slow burn because he was in the early on Wall Street Bets, so he’d be talking about it and talking about it rising. I think a lot of people turned to the internet to just start to look for outlets while COVID was on. And it just had this slow build to it. So it started to get intense. I was getting the blow-by-blow. And then it started getting really intense, coming up to that final day. And literally that conversation that Keith has with his parents when he announces how much he’s up and he’s not selling, it was not dissimilar to when our son the night before, it was like he was up this much and we’re like, “What are you doing? You going to sell? What’s going on?” Not nearly the same kind of numbers, but for him, very impactful. And watching him the next morning, every three minutes, getting up at six for the pre-market, every three minutes checking, when’s he going to get out? It’s in the stress levels trying to find that moment. When’s he going to stop? When’s too far? And he did get out with his option. He timed it perfectly, and then the market crashed the next day with the Robin Hood freeze.

Oh wow. So right before that?

Yeah, it was the day before. And then living that outrage and that incredible frustration and anger and what felt like a system rigged against them – and how you could tank the stock, and trying to figure out what happened, and seeing Elon Musk interviewing Vlad Tenev and being like, “So what’s the deal?” We try to say as true as possible: how the events happened, what actually happened, what we know about what we’ve discovered since the congressional hearings. All of that stuff we tried to embed in the film.

I didn’t know much about Keith Gill. I remember when this was happening, the media just talked about “Redditors are doing this.”

And obviously it’s these things. It’s this confluence of events that made this happen. It’s like you couldn’t orchestrate this in a vacuum. It was a perfect storm, and it turned out that the guy who had been talking about it for a year was Keith Gill.

By the way – and I know you knew it was funny because you showed it like five times – but every time Paul Dano is staring at the cat and then looks at the camera and smiles, I laughed out loud. At the end, you show the real one, but I still think Paul Dano’s is funnier for some reason.

[Laughs] Well, he’s a professional actor.

Okay, good point.

But yeah, we tried to stay so faithful. And even to the point where we have Pete Davidson playing Kevin Gill, and I’d looked at some of his social postings and it felt like a great fit. And he was.

Yeah, he’s great in this.

And the actual person does do DoorDash. He supposedly got a car – we’re not entirely sure – but it seems to be he got a car from his brother after all this happened. And then it’s like, I want to have the scene between the two of them because we know the press was trying to approach him as well. And Rebecca Angelo and Lauren Schuker Blum went back and did some research and found out that he ran the track mile naked in college in a thunderstorm, and so they wrote a scene around that. So we’re always constantly looking for the facts and drawing from those.

How worried are you about audiences picking up jargon? Do audiences know what shorting even means? I remember I learned that from the end of Trading Places and that movie doesn’t explain what they’re doing at all. So I had to look it up.

[Laughs[ We should put a Trading Place meme in there, huh? Just to explain it. Interesting thing. It’s like this is something you’ve seen in films forever and ever. It’s like even you watch The Big Short and do you really understand exactly what happens?

Well, the whole premise of that movie is the banks don’t want you to understand it.

In fact, even as much as you have Margot Robbie explaining, it still doesn’t seem to get explained.

Right, the people who run finance don’t want normal people to understand…

Exactly. But it’s a very complicated thing, like Apollo 13, do we understand exactly what they’re doing to get the spacecraft down to earth? But there was just this very basic situation happening here, which was, the big banks want the stocks to go down. The Reddit users want the stocks to go up to screw over the banks. But within that, and something that I think is incredibly tangible is they’re dealing with finance. They’re dealing with money that’s going to change their lives. When you see America Ferrera’s character and she’s up half a million dollars. The change, the impact that would have on her life is astronomical. And she can relate immediately and in a nanosecond, she can lose it all.

So, Dane DeHaan. That was incredible. I was not expecting that.

I got an incoming call from Dane that he liked to be in the movie. I love Dane DeHaan as an actor. He’s such a beautifully complex guy. And honestly, I felt awkward about it. We got on the Zoom and I’m like, “Dane, we’ve pretty much cast the film. I would love to work with you.” I said, “The only thing I have is I’ve got the manager that plays opposite of Anthony Ramos.” And he’s like, “I’ll do that.”

Oh, that’s great.

Yeah. He’s like, “I’d love to do that.” And I was like, “Are you sure?” He’s like, “Yeah, it’d be fun.” Literally, an hour later he texts me, “Hey, what if I had adult braces in a rat tail?” So immediately he started bringing stuff to that character. “I don’t think I should reveal the braces until later in the film.” And so it’s just the thing, when you’re working with great actors, they just say they’re so addicted to the process and they’re bringing ideas and they’re bringing depth to their characters. And so the complexity with which he could do those scenes, which on the page could be really simple – the insecurities, the disconnect between the common person and what they’re struggling with – it resonated. When you sit with an audience, it resonates so quickly and so strongly. It has to do very little.

I’ve been thinking about this for a few days, and keep in mind, I’ve had a fever for a few days, too. So if this makes no sense, that’s why. I’m imagining you at a bar and someone asks what you do for a living. You tell them you’re a director. They ask what kind of movies you make. What’s your answer? I ask this because you’re an enigma to me.


You’re laughing because you know that’s true.

Oh, it’s absolutely, it’s a very funny comment. And it depends on the person. It’s like, which one of my movies will this person be seeing? It’s like, I don’t think necessarily all of them.

That’s a good point. Probably not.

Sometimes they’ve seen none of them.

Oh, come on.

I can go through the list. “Have you seen I, Tanya?” “No, what’s that?” “Have you seen Cruella?” They say they don’t have kids.

Who doesn’t love Lars than the Real Girl? That is the sweetest movie ever made.

But it didn’t get to a huge audience. So that one is an unusual one. And then, of course, you’ve got to give the logline to that, which doesn’t give you the context of it.

That’s true. People are going to think it’s erotic.

You just have to see it. It’s hard to explain it, but it really, really is a heartfelt film.

Cruella is interesting. At the time, the critical reaction was a lot of hemming and hawing, but now when people talk about it, they seem to love it. It’s considered this movie everyone likes now. Do you notice that?

It’s such a stressful thing. It was also, Cruella came out a very odd time, in the middle of COVID. So that in itself was something. And I guess with Cruella, interesting thing, it’s so not like anything else that was coming out of Disney at the time. In the best sense of it. I’ve got a wonderful relationship with Disney and they really let me run with it.

Last time I talked to you, we both kind of described it as a “dark and gritty” version. And it is.

It is. And it’s not in any negative way, but every time a production head would come in to start working on the movie, on Cruella, I’d stop him and be like, “You’re not making a Disney film. We’re making an independent movie.” That’s how you need to think about it. And it would just dramatically shift everybody’s perspective. So it’s, in some ways, it was always the idea that we’re getting away with it. But it only works if people like it so it seems to be over the course of time, I’d say yeah, it’s definitely resonated.

I guess the bigger point is just, you can do a number of genres you can do a number of styles successfully. I don’t think a lot of people can do that. But at the same time, you don’t get established as someone known for a particular style.

The only two constants for me, probably, are typically it’s about an outsider. I don’t know. That’s something I wasn’t overtly trying to do. But as I look back, it’s definitely a theme.

Oh, I think that’s definitely true. Even in something like the Chris Pine movie, The Finest Hours, he’s kind of an outsider.

Yeah! He’s a marginalized character, the underdog. Nobody expects that he can get out there and do it. And then the dance with tone that I love to have, no matter what the genre, it varies. But even Fright Night has that dance of tone and comedy and horror. It’s more challenging, but it’s more gratifying to me… It’s funny, it’s like life, to me, is the way that we interact as human beings in our relationships within our families, humor is always a part of it. It’s always used. It’s either to connect or to be divisive. And I love to be able to use that in films, too, because it gets you to know the characters in a way that you can relate to. And I think that’s part of why people connect to the characters in the films because they’ve been on this journey with and gotten to know them in a way that feels very familiar.

There was this one quick moment, which is the big fuss in the movie with Anthony Ramos and in every case we’re trying to find a way they have so little real estate, which is a rare thing about this movie because there’s so many characters mingling. So they’ve got three or four scenes to make an impact and to connect with the audience. One of the scenes that’s written for Anthony is him with his family when he shows them he’s got $175,000.

At the dinner table.

At the dinner table. We all land together and meet for the first time in that apartment on location. Anthony’s meeting these actors for the first time. I said, “I would like you guys to speak in Spanish.” Anthony’s saying, “I’m not great with that.” But it’s not uncommon at all, in a bilingual family, people will be speaking Spanish and English at the same time, conversing that way. So we’re like, “Great. The parents can speak in Spanish, you can speak in English.” And then the mother is like, “I would probably switch to English when it gets serious.” It’s great. So it’s sort of this organic approach to it, which I love. But then it gets to the end of the scene and she’s like, “Be careful with this. It can be like a drug.” And it gets very serious and it’s lacking. I’m not quite understanding of the whole relationship there. So I said, “Anthony, when she says that, take the phone and sniff it like a line of coke.” And then she just spontaneously slaps him over the shoulder. I didn’t ask her to, but immediately started to get their relationship.

That’s great.

They can tease each other and be direct with each other and undercut each other. And you understand the family dynamic in a three-second moment.

I’m looking forward to people seeing this in the theater, and I know it’s soon…

Very soon!

It was good to talk to you, thank you for putting up with my voice.

Try and get some rest!

Oh that’s the next thing I’m doing.

‘Dumb Money’ opens in theaters on September 29th. You can contact Mike Ryan directly on Twitter.