If good things should happen to good people–and bad things should happen to bad people–then whose lives should be made into TV shows? That’s the question posed by three splashy (and equally problematic) Big Tech docudramas playing out this spring.
Disgraced disruptors Elizabeth Holmes, Travis Kalanick, and Adam Neumann are making headlines again as Hulu’s The Dropout, Showtime’s Super Pumped: The Battle For Uber, and Apple TV+’s WeCrashed adapt the ex-CEOs’ oustings into episodic character studies—all starring A-list actors.
Amanda Seyfried anchors The Dropout as Theranos founder Holmes, whose medical testing company doubled as a dangerous fraud. Joseph Gordon-Levitt stars in Super Pumped as former Uber CEO Kalanick, who resigned amid allegations at the height of #MeToo. As for WeCrashed, Jared Leto and Anne Hathaway appear as the hard-partying Neumann and his wife Rebekah, whose shared narcissism all but destroyed their co-working startup WeWork.
Each limited series (or, in the case of Super Pumped, self-contained season of a planned anthology) adapts a book or podcast, summarizing months of news stories and market mania that unfolded in real-time not so long ago. To make matters even more redundant, The Dropout and WeCrashed were beaten to market by documentaries The Inventor: Out For Blood In Silicon Valley and WeWork: Or The Making And Breaking Of A $47 Billion Unicorn, released in 2019 and 2021 respectively.
This sort of narrative double-dipping tends to dilute source material and alienate audiences. But the promise of highly skilled TV stars skewering Silicon Valley helped transform the scheduling coincidence into something of a pop culture event. First-looks revealing outrageous prosthetics and trailers teasing unblinking eyes arrived like sideshow advertisements, all but commanding: Come see the altruistic heroes of Hollywood fight the fiendish freaks of big business–now via caricature!
Seyfried, Gordon-Levitt, Leto, and Hathaway are the right actors to do it, to be sure. Their performances are funny, well-informed, and smart (as was to be expected from these award-winning ringers). And yet, there is an underlying paradox in this trio of titles: By putting some of Silicon Valley’s most notorious wrongdoers back on screen, isn’t Hollywood celebrating their misdeeds–even unwittingly?
Storytelling requires highs and lows, meaning that characters (no matter how detestable) must experience change. Here, that means audiences must watch as true-to-life tyrannical titans of industry rack up as many brag-worthy wins as they do cataclysmic losses. For every boardroom embarrassment, there is a spare-no-expense rager; for every crisis of confidence, a self-assured jam session; for every fall from grace, a view from the top of the world.
To get to the declines of Holmes, Kalanick, and the Neumanns, we must first weather their reward-laden rises—a frustrating way to ensure some viewers only ever see the victories. Super Pumped’s third episode, for example, centers on Uber’s never-ending pissing contest with Lyft. It’s practically an end-zone dance for Kalanick, whose business strategies worked wonders on that one problem at that one time.
Similarly, when we are taken back to the entrepreneurs’ origins–namely, the impassioned speeches in which they first made utopian promises to their employees and investors–these would-be Bill Gates look less like liars and more like wunderkinds led astray. The revolutionary ideas they first spoke to are extra compelling against the backdrop of the ongoing Great Resignation. Think Mark Zuckerberg’s relentless refusal to accept the Harvard establishment, as seen in David Fincher’s (increasingly out-of-touch) The Social Network, and you get the idea.
You don’t root for Holmes, Kalanick, or the Neumanns in quite the same way you might have once admired the flip flop-wearing wunderkind played by Jesse Eisenberg. But that’s because each show grapples with the ethical slipperiness of its subject matter differently—and with varying degrees of success.
WeCrashed morphs the Neumanns into farcical creatures of high-camp, making their happiest moments into cringe-inducing displays of tone deafness. Super Pumped blurs the lines of reality and fantasy, letting Kalanick’s Goliath vision of himself give way to a fighter not half as smart as David. The Dropout plays Holmes as a hyper-driven sociopath, giving Theranos’ intense business arc the breakneck pacing needed to match her rapid psychological unraveling.
These strategies toward nuanced portraits of interesting figures work some of the time. Still, it’s painfully easy to imagine the shows’ living-breathing inspirations enjoying lighter scenes and even being happy they exist at all.
You can almost picture Kalanick cracking open a cold one while marathoning JGL’s meanest monologues—or envision the Neumanns, lounging in their still-perfectly agreeable living quarters and soaking up comparisons to WeCrashed’s very good-looking lead actors. Maybe Holmes is the odd one out, considering she’s still facing prison time. But an exciting new personal connection to Mamma Mia! counts for something, right?
These heavy silver linings for Holmes, Kalanick, and the Neumanns reflect an irritating imbalance inherent to Silicon Valley villains. Self-important public figures with this much power tend to play outsized roles in their victims’ lives—a dynamic that too often continues even after the evil-doers’ comeuppance. Now, Hollywood is forwarding that regrettable reality by retelling these all-too-recent true stories as glossy portraits that prioritize the villains over the people they harmed—when it should probably be the other way around.