‘Dumb Money’ Director Craig Gillespie on His Personal GameStop Stock Craze Experience and Why Paul Dano and Pete Davidson Are a Perfect Duo

The tale of an unlikely folk hero’s rise during the not-so-distant past is front and center in Craig Gillespie’s latest film, “Dumb Money.” Paul Dano stars as Keith Gill, a financial analyst who made YouTube videos as Roaring Kitty, and generated a mass following from the basement of his home outside of Boston. Gill also posted regularly on the Reddit meme-stock forum WallStreetBets, a popular virtual gathering spot for amateur investors, a.k.a. “dumb money.”

Gillespie’s “Dumb Money” follows Gill in 2020, during the height of the Covid-19 pandemic, when he led an online uprising against the big-shot finance guys out to short-squeeze the GameStop stock. “Dumb Money” shows Gill encouraging his followers, a handful of whom are portrayed here, to buy shares of the stock to drive up its value. This does not sit well with Gabe Plotkin (Seth Rogen), the founder of Melvin Capital, who loses billions as Keith makes several million. It also ends up spelling disaster for the co-founders of Robinhood (portrayed by Sebastian Stan and Rushi Kota), the app that retail investors used to purchase shares of the stock.

Director Craig Gillespie, who has previously directed riveting real-life stories such as “I, Tonya” and the Hulu limited series “Pam & Tommy,” had an in-depth conversation with Entertainment Voice, in which he discussed working with Dano, reteaming with Rogen, and his personal connection to this bizarre moment in stock market history.

You experienced the GameStop stock phenomenon firsthand during the pandemic when your son became an investor. Let’s talk about what it was like living through that with him and how it shaped your perception of the stock market.

It was interesting. I mean, it wasn’t on my radar, honestly, at all, except for the fact that he would be constantly coming down and mentioning this Wall Street ban and what was going on there. He was in early on. So, as the movement would start to happen, we’d be hearing about it. Elon Musk would tweet “GameStopped,” and you get to see a bump in the stock and the excitement from the WallStreetBets group, and then Mark Cuban would chime in with something on Twitter, and again, there’d be another little boost, and it just kept percolating and slowly building, as you see in the film. 

But, then it got into this very intense period… this 24 hours where it spiked to 400. And at that moment with him in the house, the intensity of watching the [global] stock market [at all hours], checking it every three minutes, he was really trying to time it just very much like our characters in the film… He got out just at the right time. I lived this whole thing with him, but then the surprise, the frustration when Robinhood shut down the buy option, that sheer outrage that was happening online… that’s all of that intensity that I was witnessing through him. That’s what I wanted to capture in the film. It was such a riveting, intense time.

After that epic roller coaster, you received Lauren Schuker Blum and Rebecca Angelo’s screenplay, which was adapted from “The Antisocial Network” by Ben Mezrich. What was it like working with them to bring the screenplay to life?

I was very familiar with them already. They had sent me a script, “American Right,” which I almost did, except the timing didn’t work out. [It was] about the political system going on in the United States. I love that script. That was very much on my radar to the point that we were now working on another script, which was “Chippendales.” And, we were working on that while they were writing “Dumb Money.” So we were talking about “Dumb Money” all the time, but it hadn’t occurred to me [to direct], because I wasn’t available and I was about to shoot this other film, but that film, for various reasons, imploded, and the next day, they sent me the script. I read it immediately and I knew it was going to be good because… they’re such intelligent, thoughtful writers, but the layering of it, the intensity, that pressure build-up that I was hoping for, it was all baked into the script.

Interestingly, because it was all happening in real time and the congressional hearing and the fallout of that hadn’t resolved itself until [after] I [came onboard the project]. Going back and immediately looking at Keith Gill and seeing that testimony at Congress, I was like, “This is where our film has to end.” That wasn’t actually in the script, originally. We got to put that in and build towards that moment and you sort of layer in the touchstones for that because it was a great rallying point for everyone.

Keith Gill, played by Paul Dano, is an intriguing character. Even though he holds much influence over his followers and comes to be worth millions, he manages to stay humble. What was it about Dano that led you to cast him for this role, and what was it like working with him?

Paul has such a range as an actor. He’s always been on my radar, and he gives such a beautifully nuanced, contained performance so often. Even that year, he was doing “The Batman” and “The Fablemans.” The breadth of his performances are amazing. And, as I was trying to figure [casting] out, my son was like, ”If you like Paul, you need to watch “Swiss Army Man.” The exuberance that he has in that, and the joy and the innocence, with these qualities that I thought, “Oh, wow, that is so similar to what Keith has when he posts these videos.”

When Paul and I spoke, we talked about it, we connected on the material. In terms of working with him, he just elevates everything… He was doing all of his homework. He was watching all of the posts that Keith had done, finding any information that he could on him. 

[Paul is] classically trained. He’s been in theater since he was 11, and I [paired him] with Pete Davidson [as his brother], who is a whirlwind. He is just so spontaneous in the best sense of the word, goes off instinct. And, I gotta say, I was so excited to see those two together, to see what would happen in the room. In the best way, they just react to each other, as opposed to acting. And, so whatever Pete would throw at Paul, he’d give it back, and he’d just be happy to go off script. They sort of created this magic together. 

Seth Rogen as Gabe Plotkin is on the opposing side of Keith, but he is not as insufferable as he could be, and there are parallels between him and Keith. Tell us about that character and what is was like working with Seth for this role.

It was very important to the writers and myself that this wasn’t black and white. Humanity is more complicated than that. The internet has a way of distilling things down to a very basic level, and we wanted to show that even though all this was happening, and that [the wealthy investors] were being targeted, at the end of the day, it’s a human being. It’s a person with a family and children who is a good father and husband. And, to show that, it adds to the complexity of what’s going on with everything. 

With Seth, the opportunity to cast against type, I always find interesting. You’re not expecting it; you think he’s going to be on the side of the underdogs. For him to be able to bring that humanity to it, but still stay true to what was going on and the moves that were being made, I think it makes it a much more interesting character.

He’s so versatile. Obviously he’s done some drama in the past, but I love to work in the space of drama and humor. And, he has a beautiful way of being able to still find humorous moments that aren’t at the sacrifice of his character. The situation just makes you chuckle, it makes you smile, but he’s doing it in a very deft way because people know him for his humor and they expect it, but he’s got to underplay it so that we still are invested in his character on a dramatic level. I thought his performance was amazing. 

Then we have the fictional characters representing the “dumb money,” including Jenny, the nurse and single mom played by America Ferrera. How did you determine which types of people you wanted to follow in the story?

We really wanted to represent the different motives for people that were on WallStreetBets. There were people there just to make money. There was a large group of people who were about the movement and really sticking it to Wall Street, and showing this frustration at the disparity of wealth. There were people that were conflicted; they wanted that and the money. 

In America’s case, we wanted somebody who really had that voice for the frustration, for the feeling of the people who are marginalized, that feeling that the system is rigged against them. And, in many cases, it is. You know, the lack of government handouts that was happening at the time, being an essential worker, there was so much that [Jenny] had to shoulder.

I needed somebody that could have that fierceness, have that conviction. And, again, keeping with the style of the film, that sort of deft touch for humor that America has. She can dance between the two, and just be really accessible to the audience because, you know, sometimes when somebody gets on a soapbox, it gets a little bit grating, but she has this way of bringing the audience in to connect with her and root for her that is just wonderful.

Dumb Money” releases Sept. 15 in select theaters and opens Sept. 29 in theaters nationwide.