In the second episode of Inventing Anna, a new drama series that chronicles the rise and fall of infamous fake German heiress Anna Delvey (Julia Garner), fashion stylist Val (James Cusati-Moyer) outlines a sure-fire way to spot an aristocrat from a thirsty wannabe socialite. It’s all in the wine order.

“New money always gets the most expensive bottle. Anna ordered like generational wealth: regions, years… Anna was the real deal,” gushes Val. However, the inconvenient truth is that Anna was not a blue blood with intermittent cash-flow issues caused by an overbearing father who limited her access to a hefty trust fund. Rather, she was Anna Sorokin, the daughter of a truck driver and a housewife who migrated to Germany from Russia during her childhood.

In 2013, Anna was among the many thousands of 20-somethings who flocked to New York with little more than lofty dreams of making it in America. Remarkably, armed with an indeterminate European accent, sloppily glamorous aesthetic and unbridled chutzpah, she soon infiltrated high society. Once there, Anna swindled acquaintances, hotels, banks and other businesses out of more than $US200,000 and attempted to secure a $US22 million loan with fraudulent paperwork before being arrested in 2017 and going on to serve just under four years of a four-to-12-year prison sentence.

The so-called “SoHo grifter” story first entered the public domain via Jessica Pressler’s 2018 New York magazine article “How Anna Delvey Tricked New York’s Party People”, upon which the Shondaland-produced Inventing Anna is based. Eight of the series’ nine episodes home in on various individuals who were drawn into Anna’s orbit, with the conflicting recollections of uppity society woman Nora (Kate Burton), tech-futurist boyfriend Chase (Saamer Usmani), hotel concierge and aspiring filmmaker Neff (Alexis Floyd) and others working to suggest that Anna was more layered than a matryoshka doll.

The show offers viewers the vicarious thrill of watching Anna chartering a private jet to a conference hosted by Warren Buffett one day and chowing down at New York’s trendiest restaurant with former child star Macauley Culkin and disgraced hedge-fund manager Martin Shkreli the next, all without a functioning credit card. The upbeat soundtrack featuring Megan Thee Stallion, Doja Cat, Rico Nasty, Lion Babe and Australian artist Tkay Maidza adds to the sense of euphoria.

On a deeper level, Inventing Anna attempts to shed light on what motivated Anna’s schemes. Was she merely a materialistic girl who scammed to support her penchant for designer wares or a sad loner attempting to buy friendship? Or had she internalised the “fake it till you make it” mantra of the entrepreneurial American so effectively that she believed her own tall tales?

Anna maintains she was building the Anna Delvey Foundation, a members-only club for the global art world elite, and exercised artistic licence to secure the connections and capital necessary to get the project off the ground. Stories of ambitious young women who build “girlboss fempires” in the cut-throat, male-dominated business world are millennial lore. Take Audrey Gelman of women’s workspace The Wing, Leandra Medine of fashion blog Man Repeller and Sophia Amoruso of e-commerce start-up Nasty Gal: all women who built once-thriving businesses in their 20s by practising “lean-in feminism”, which encourages women to self-actualise through corporate success.

Never mind that the archetypal girlboss is typically white or white-passing, comes from money and treats her (often female) employees terribly. As Jia Tolentino writes in her essay “The Story of a Generation in Seven Scams”: “The feminist scammer rarely sets out to scam anyone, and would argue, certainly, that she does not belong in this category. She just wants to be successful, to gain the agency that men claim so easily, to have the sort of life she wants.” At one point, a delusional Anna chastises older male lawyers and investors for not taking her seriously because she’s an attractive 25-year-old woman, although – given she is living a lie – they are correct to question her authority.

Anna cultivates transactional relationships that she then deploys to advance her interests – as do many of the women around her, albeit more discreetly. Striving Vanity Fair photo editor Rachel (Katie Lowes) is drawn in by Anna’s perceived ability to facilitate luxurious experiences, but ends up stiffed with a $US62,000 bill for a vacation to a Moroccan riad favoured by the Kardashians. While Rachel maintains that meeting Anna was “the worst thing that ever happened to me”, she capitalises on her misfortune by penning a juicy personal essay and securing book and TV deals worth hundreds of thousands.

Vivian (Anna Chlumsky), a dramatised version of journalist Jessica Pressler, encourages Anna to reject the plea deal she is offered and promises to make her famous. Vivian isn’t motivated by concern for Anna but by the fact that without a trial she will have no story. With her career in tatters and a baby on the way, Vivian sees Anna as an opportunity to salvage her journalistic reputation before it’s too late. She goes into labour at her office but refuses to leave before securing a critical source needed to file the article. In a scene that reveals the horrors of the American workplace, her colleagues cheer her on as she grimaces through contractions. Given the grim prospects for ascension through aboveboard channels, it’s hard to blame Anna for cutting corners.

At a swanky art opening, Anna encourages a monied stranger to purchase a Cindy Sherman film still. When the woman dismisses the work as “just another 8 x 10 of her playing dress-up”, Anna passionately defends Sherman’s practice of photographing herself dressed as female archetypes. Blurring life and performance art, Sherman would sometimes inexplicably appear at work or an art opening dressed as a nurse or pregnant housewife. By inhabiting a partly real, partly fabricated “Anna Delvey” character, Anna gestured towards Sherman and other artists, such as Lynn Hershman Leeson and Amalia Ulman, who use alter egos to explore identity, femininity and authenticity. It’s possible that Anna saw her actions as being in service of art.

Like Sherman, Anna understands the power of image. The Instagram account @ annadelveycourtlooks chronicles Anna’s trial outfits, which were created with the assistance of fashion stylist Anastasia Walker, who has worked with Courtney Love, Chance the Rapper and T-Pain. The looks mixed designer brands such as Yves Saint Laurent and Victoria Beckham with chain store finds from Zara and H&M, favouring a restrained black, white and beige palette. On April 24, 2019, on the second day of jury deliberations, Anna wore a virginal white baby-doll dress, black ballet flats, her signature square Celine glasses and a thin, black ribbon tied around her neck, evoking a vulnerable naif that would have made Sherman proud.

Whatever you think about Anna’s character, it’s hard to argue with her assertion that “Anna Delvey is a masterpiece, bitches”. While Inventing Anna is not quite so triumphant, it offers an entertaining portrayal of a young scammer and the elite world that embraced her. 

Inventing Anna is available now on Netflix.

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