“You know what I’ve noticed? Nobody panics when things go according to plan. Even if the plan is horrifying! If, tomorrow, I tell the press that, like, a gang banger will get shot, or a truckload of soldiers will be blown up, nobody panics, because it’s all part of the plan.”

That’s dialogue delivered by Heath Ledger’s Joker in The Dark Knight. You might hate Batman in particular or superhero movies in general, but the power of that dialogue cannot be denied. It posits a truth that hasn’t changed since the earliest days of hunter-gatherers scampering across the plains. That truth is; there’s a certain way things are supposed to go. 

If you work hard, you’ll advance in life. Bad people will be punished while good people will be rewarded. One of my favorites is that the rich became rich due to hard work, and not a mountain of advantages. Once in a while, though, the plan goes haywire. When that happens, to paraphrase the Clown Prince of Crime, people start losing their minds. That’s the premise of Dumb Money, a comedy based on events that are too ludicrous to be made up.

First thing, do you know what a short squeeze is? I certainly didn’t, because finance in general is confusing and frightening to me. To quote Investopedia, “A short squeeze is an unusual condition that triggers rapidly rising prices in a stock or other tradable security. It occurs when a security has a significant amount of short sellers, meaning lots of investors are betting on its price falling. The short squeeze begins when the price jumps higher unexpectedly and gains momentum as a significant measure of the short sellers decide to cut losses and exit their positions.”

The most famous recent example of a short squeeze happened in 2021. We’re introduced to the architect of that moment, Keith Gill (Paul Dano). By day he toils anonymously for MassMutual as a financial analyst. He’s better known as Roaring Kitty, an obscure Redditor on the wallstreetbets Subreddit.* He’s smart, very smart, and he’s come to believe something that sounds insane but quite possibly isn’t. Keith believes in potential. His numbers don’t lie. He’s found a modest stock offering with the potential to blow up.

Keith has analyzed the stocks for video game retailer GameStop. Shares are cheap. He believes that they’ll skyrocket. His wife Caroline (Shailene Woodley) believes in him, and supports his decision to buy massive amounts of GameStop stocks. On his RoaringKitty channel, Keith tells his followers what he’s doing and why. His decisions affect the stock market and the lives of real people, including:

• Keith’s dirtbag brother Kevin (Pete Davidson), their mother Elaine (Kate Burton), and father Steve (Clancy Brown).
• Jenny (America Ferrera), a nurse and single mom looking for a little financial breathing room.
• Marcus (Anthony Ramos), a GameStop clerk stuck dealing with a lousy boss (Dane DeHaan).
• Riri (Myha’la Herrold) and Harmony (Talia Ryder), a pair of college students who have found each other and found a way to pay off their massive student loans.
• Gabe Plotkin (Seth Rogen), the founder of Melvin Capital Management and his offbeat partner Steve Cohen (Vincent D’Onofrio).
• Vlad Tenev (Sebastian Stan) and Baiju Bhatt (Rushi Kota), the founders of financial tech company Robinhood.
• Ken Griffin (Nick Offerman), a hedge fund manager who wields enormous financial power with zero responsibility.

About this point in the review, you might be thinking to yourself, “A comedy about stocks? Ugh, pass.” Trust me when I tell you that director Craig Gillespie is the right person to helm this story. As the director of the entertaining I, Tonya, Gillespie knows how to jump into a niche subject and extract the relatable madness within. Dumb Money is relatively briskly paced, and Gillespie expertly hops throughout his large cast of characters. He lingers just long enough to give us an idea of who these people are, and he pumps the brakes equally in moments of drama and comedy.

Screenwriters Lauren Shuker Blum and Rebecca Angelo do an awful lot right in their clever screenplay. They know that the majority of viewers aren’t exactly well-versed in finance. As a result, they take a page from jargon-heavy films like Apollo 13 and Master and Commander by using a ton of impenetrable terminology, but in a way where we understand the gist of things. More importantly, they show us in brush strokes how the short squeeze makes the characters feel. Do they feel desperate? Triumphant? Quietly confident? Angelo and Blum know the most important lesson of screenwriting, which is that it’s more important to learn how the characters feel about the story that the story itself.

I’ve come to realize that one of Craig Gillespie’s talents as a filmmaker is the ability to direct actors with a well known persona in a unique way. His cast is crammed full of rock-solid performers who absolutely understand the assignment. Paul Dano originally came to prominence playing lunatics like The Riddler in The Batman and Eli Sunday in There Will Be Blood. Recently, he’s gotten to take a crack at more sympathetic characters. As Keith/Roaring Kitty, Dano plays a good husband, a good father, and the rarest of things – a decent person on the internet. The flip sides are Seth Rogen as Gabe Plotkin and Sebastian Stan as Vlad Tenev. Both are charismatic and likable performers, and both tend to do their best work playing scumbags who aren’t as smart as they think they are.

Once in a while, the plan falls apart. Everyone loses their mind. Sometimes, things work out the right way as opposed to the planned way. Dumb Money might not be about a gang of steely-eyed professionals or a movement that stands up for what’s right. Instead, it’s about a moment where mostly the right things happen to mostly the right people. These days, I call that a win.

*The film portrays wallstreetbets as a little grimy but ultimately goodhearted. My kid, who knows a thing or two about both Reddit and finance, tells me that wallstreetbets is an absolute sewer. Enter it at your own risk.

Tim Brennan Movie Critic

Tim has been alarmingly enthusiastic about movies ever since childhood. He grew up in Boulder and, foolishly, left Colorado to study Communications in Washington State. Making matters worse, he moved to Connecticut after meeting his too-good-for-him wife. Drawn by the Rockies and a mild climate, he triumphantly returned and settled down back in Boulder County. He's written numerous screenplays, loves hiking, and embarrassed himself in front of Samuel L. Jackson. True story.