For the last few years, scammers and corporate con men and women (but especially women) who tricked America’s elites have captured headlines. But in the last few months, the most prominent ones got the Hollywood treatment from major streaming sites: swindler-socialite Anna Sorokin in Netflix’s “Inventing Anna,” famous fraudster Elizabeth Holmes in Hulu’s “The Dropout,” and WeWork’s culty co-founders Adam and Rebekah Paltrow Neumann in Apple TV+’s “WeCrashed.”

There’s too much of this content out there for any one person to take in, unless you’re me and you’re obsessed with so-called “girlbosses,” a term born in the Sheryl Sandbergian “Lean In” moment for women succeeding in the corporate world. It became a joke when many of the so-called girlbosses turned out to be as bad as the boy bosses, including, allegedly, the “Nasty Gal” founder who popularized the phrase. It’s been zombified into a running internet joke in this post-Elizabeth Holmes moment and is usually half-aspirational and half-tongue-in-cheek.

This final crest in the media wave of these stories, which happened before COVID-19 hit, comes as America’s richest men have made billions during a pandemic that saw millions of women lose jobs.

I watched all of these shows and binge-consumed the journalism that birthed them (although I didn’t watch Showtime’s “Super Pumped,” about forced-out Uber founder Travis Kalanick; it doesn’t to my knowledge include much girlbossery, has a lower Rotten Tomatoes rating than any of the three below, and requires a Showtime login I do not have).

Here are my thoughts on the big three, whether you should watch them, and whether you should believe them — because these shows, like the girlbosses they’re about, tend to bend the truth.

“Inventing Anna,” Netflix

Is it good? No.

Is it factual? No.

Does it girlboss? Yes.

“Inventing Anna” is heavily invented itself: each episode starts with a tagline/disclaimer saying “This story is completely true. Except for the parts that are totally made up.” TV super-creator Shonda Rimes (“Grey’s Anatomy”) leaves it up to you to decide whether this is referring to the lies Anna Sorokin (Julia Garner, “Ozark”) tells New York’s elites as she convinces them she’s a German heiress, or to the show itself.  


But it’s a double-entendre. Though the story follows the rough shape of Sorokin’s young life, many characters are amalgams of real people or spun from whole cloth — most notably, the colead, journalist “Vivian Kent” of “Manhattan magazine” (Anna Chlumsky, “Veep”) based on Jessica Pressler of New York magazine (this is the second time this has happened to Pressler, who wrote the article inspiring the 2019 movie “Hustlers” and Julia Stiles played a fictional version of her). This allows Chlumsky’s character to do things an ethical journalist wouldn’t do — tell Anna’s lawyer (Arian Moayed) she’s on their side, or break-in to Anna’s parents’ home in Germany — and the cumulative effect is worse when she does things Pressler actually did, like buy Anna clothes for court.

But where “Inventing Anna” insists on fidelity to real life, it’s annoying, such as in Garner’s uninventive portrayal of Anna. It’s a dead-on impression of Sorokin, according to Pressler and others who know the real Anna, it makes for a dead-on-arrival performance. A good impression never equals good acting, and because Anna isn’t a public figure we can’t tell how good the impression is anyway — so it seems like an in-joke.

This results in a show that works hard to make Anna, who could be one of the more sympathetic girlbosses on the list because of her ambitious outsider status, seem as unsympathetic as possible.

“The Dropout,” Hulu

Is it good? Yes.

Is it factual? Mostly.

Does it girlboss? Yes.

I can’t say much about “The Dropout” that hasn’t been said better — critics liked it the most out of any of these shows, it’s fairly true to its namesake podcast and John Carreyrou’s book “Bad Blood,” and Amanda Seyfried balances an OK Elizabeth Holmes impression with a thoughtful interpretation of the woman who wanted to be the next Steve Jobs. 

But I think this show falls short of truly great TV, and much of that faltering comes from showrunner Elizabeth Meriwether (“New Girl”) and her team’s propensity to amp up true-life details in hard-to-believe ways, in the service of dramatic effect.


In the end, when Holmes’ company comes crashing down, she’s chased from its ’ empty headquarters by her former counsel (Michaela Watkins) telling her she hurt people over and over. It’s over the top and falls flat, because Watkins’ character — a fictional amalgam of several lawyers — was right there at Holmes’ side through all of it. Carreyrou’s book, by contrast, ends with Holmes’ presentation at a chemistry conference, where she wows with her characteristic persuasiveness but at the end, a lone voice in the crowd yells “You hurt people.”

These blown-up details are for pointing out how much damage Holmes did, but the show is lighter on the corporate and media culture that failed to catch her for so long and rewarded her false narratives.

“WeCrashed,” Apple TV+

Is it good? Not in the classic sense.

Is it factual? Sure.

Does it girlboss? Right through the glass ceiling.

If you want a fine show anchored by a good performance, you can stop reading — “The Dropout” is that show. But sue me: despite the fact “WeCrashed” starts poorly, ends iffy, and isn’t well-written, I was more entertained.

This has everything to do with the two leads, Jared Leto and Anne Hathaway, as Adam Neumann and Rebekah Paltrow Neumann respectively. The internet has had a lot of fun hating on Leto in the last year, from his fat suit Super Mario impression in “House of Gucci” to his starring role in “Morbius,” the most widely-mocked superhero movie in years. 

But in playing Neumann — a deeply un-self-aware man who reportedly wanted to become “president of the world” and aspired to live forever — Leto’s maximalist tendencies work. After all, we’re talking about an actor who is sort of a cult leader himself. Rebekah in this show has enough girlboss energy for them both, allegedly firing employees for “bad energy” and declaring that she herself is “the soul of the company.”

Leto and Hathaway are not doing good impressions of the Neumanns, they are riffing, and watching their shared psychosis as their unicorn company’s fake valuation soars into the billions feels like more of a spiritual condemnation of laissez-faire capitalism than a corporate comedown story.

I think one of the reasons we’re obsessed with girlboss scammer TV is much the same reason audiences in decades past loved to see supposedly “promiscuous” women murdered in slasher movies, or in centuries past, burned at the stake for being witches: America loves to see a woman punished for grasping at power. In TV and often in reality, women are given less room to mess up in the corporate world anyway: “The Dropout” in particular spends some time focusing on how Holmes’ fraud will make it even harder for women in Silicon Valley. But it feels like the show blames Holmes for that.

“WeCrashed” is different. These two essentially get away with a lot of money — though the show tries to convince you otherwise with an eleventh-hour twist that ends its finale really poorly — because it’s convincing you that the actual problem here is not the people. It’s the system that rewards them.