Joseph Gordon-Levitt plays a sensitive, smirking, volatile Travis Kalanick in Super Pumped: The Battle for Uber, the newly debuted Showtime TV show based on Mike Isaac’s book of the same name. Season One chronicles the rise and fall of Uber, the global ride-hail giant that Kalanick founded and grew to a $68 billion company before he befell a cascade of scandals and was ousted by his own board. The pilot episode, set to a thumping score, suggests a glossy thriller about a brilliant outsider who may transform not just the taxi industry but the world. In the series, Gordon-Levitt’s Kalanick meditates with Arianna Huffington (Uma Thurman) in a candlelit garden and squares off with Benchmark powerbroker Bill Gurley (Kyle Chandler). He parties. He swaggers. He does a lot of defiant yelling.
Gordon-Levitt is the latest acclaimed actor to portray an infamous businessperson in a Hollywood drama. He’ll soon be joined by Amanda Seyfried as disgraced Theranos founder Elizabeth Holmes in Hulu’s miniseries The Dropout, and Jared Leto and Anne Hathaway as WeWork co-founder Adam Neumann and his partner, Rebekah, in Apple’s limited series WeCrashed. Before this recent spate of real-life tech dramas, there was Damian Lewis as billionaire hedge fund manager Bobby Axelrod in Billions, a character partly modeled on SAC Capital founder Steve Cohen; Ryan Gosling in The Big Short as Deutsche Bank salesman Jared Vennett, based on Deutsche trader Greg Lippmann, who profited on the collapse of the housing market; Justin Timberlake as serial entrepreneur Sean Parker in The Social Network; and, of course, Leonardo DiCaprio as profane and corrupt stockbroker Jordan Belfort in Martin Scorsese’s Oscar-nominated biopic The Wolf of Wall Street.
There is a broader debate to be had about whether these productions irresponsibly glamorize white-collar crime, but I have a narrower objection: The actors who play the chief bad actors in these stories are always hot, even when their real-life counterparts are not. This sends exactly the wrong message on a level even more fundamental than turning corporate scheming into zippy entertainment. When we rechristen Kalanick as Gordon-Levitt, Belfort as DiCaprio, and Lewis as Cohen, we prove that bad behavior pays in more ways than one. The subtext is clear: if your actions are extreme and absurd enough, they are also great material. You can sell life rights! Write a book! Go on the conference circuit telling your tale! As long as you don’t end up in prison—or, actually, even if you do—a good script and a hot actor can not only help to launder your reputation, but manifest a cooler, sexier you. Becoming famous by way of an attractive Hollywood face is a special kind of reward.
The most egregious case study remains the real wolf of Wall Street, Belfort, a man who was not bad-looking in his heyday but did not exactly have the face of a generation’s beloved heartthrob either. After defrauding investors of millions of dollars at penny-stock shop Stratton Oakmont in the 1990s, Belfort pled guilty to securities fraud and money laundering. He landed in federal prison in California, where he served 22 months of a four-year sentence and began work on his best-selling memoir. The Wolf of Wall Street nabbed him an advance of more than $1 million from Random House, plus another $1 million in film rights. Martin Scorsese’s antic, cheerfully profane film version was critically well-received and earned five Oscar nominations, including best actor for DiCaprio.
Belfort has griped that Scorsese’s interpretation makes it seem like he tried to “rip people off” when he wanted to “make them money” and “help build America.” That hasn’t stopped him from capitalizing on the film’s success and integrating the Hollywood portrayal into his new identity as investment and sales guru and ladykiller. Belfort’s social media feeds are sprinkled with clips and memes from the film, and he delights in talking about the time he spent with DiCaprio. “Obviously he killed it; he was spot on,” Belfort declared of DiCaprio to his 3.6 million TikTok followers in a post last year, looking decidedly un-Leo-like at such close range. DiCaprio’s Wolf of Wall Street is also a fixture of Belfort’s sales training program. At a sales master class he held in New York City a few years ago, for example, Belfort instructed audience members on pitching techniques by screening clips from The Wolf of Wall Street and then pausing to narrate DiCaprio’s lines himself, a bizarre display of life imitating art imitating life.
Super Pumped careens in a possibly even more absurd direction by casting Gordon-Levitt as Travis Kalanick, a very normal-looking man who in reality bears far more resemblance to co-star Kyle Chandler than any other actor in the series. Gordon-Levitt, the onetime teen pin-up who went on to steal manic pixie dream hearts in (500) Days of Summer, uses his natural charisma and sly smile to dubious effect as Kalanick, whom the show portrays as an increasingly erratic but still empathetic figure. It’s a perfect exhibit in how a pretty face with magnetic screen presence can soften the slimy, shifty qualities that many of these people exude in real life.
In a recent interview with Late Show host Stephen Colbert, Gordon-Levitt had plenty of criticism for Kalanick and Uber, alluding to how the company systematically evaded rules and law enforcement with a software program it called “greyball.” But, Gordon-Levitt cautioned, “I’m not a journalist, right, so it’s not my job just to say what happened, it’s my job to say how it felt. And I think he was a really exciting guy to be around.” With Super Pumped, Gordon-Levitt is helping to transform Kalanick into that flawed, exciting guy for a global audience, his amiable, boyish face the perfect advert.
The examples go on and on: It feels almost unkind to instruct you to Google Steve Cohen and Damian Lewis side by side. And if social media has taught us anything, it’s that everyone is a little vain and worries about their image. Scammers, petty criminals, and powerful business people bent on fame and glory are certainly no exception. So why give them the satisfaction of being played by a hot actor in a dramatization of their downfall? Why not let them worry that should the scheming and law-breaking go wrong, it might not only be their actions that get critiqued on the big screen, but also their very image? What if business leaders who did bad things didn’t expect to bask in the golden glow of DiCaprio or the nerdy cuteness of Gordon-Levitt when their stories made it to film, but rather feared being introduced to the public as unattractive or merely average, which the vast majority of them are? I’m not saying this would prevent the next WeWork, but come on: Why not turn a small perk of gross malfeasance into an equally small deterrent? People will keep making films and TV shows about the Jordan Belforts and Travis Kalanicks of the world because we love a heist and a scandal. Crime will still pay, in a way. It just doesn’t need to come with a makeover.
