Screengrab via Netflix.

Remember When Armie Hammer Played a Scammer on ‘Gossip Girl’?

Anna Delvey, eat your heart out.

by Andrea Whittle
Mar 29 2019, 1:13pm

Screengrab via Netflix.

Towards the tail end of the second season of Gossip Girl, a guy named Gabriel Edwards (played by an awkwardly deadpan Armie Hammer) shows up wearing a too-big pinstriped suit and stirs up a whole bunch of Network TV Drama. We first meet him in a lounge at Teterboro Airport, where he, Serena van der Woodsen and Poppy Lifton are about to kick off an impromptu trip to Spain. He introduces himself to Serena and claims to have met her years earlier at Butter (an exquisite early 2000s nightlife reference).

Since this isn’t HBO, we never do get to see what happens in Spain. But by the time we cut to the next episode, Gabriel crashes a seder dinner at the Waldorfs, sweeps Serena off her feet with lines like “I only have eyes for one girl, and she’s the most exquisite thing in the world,” and starts glad-handing every parent on the Upper East Side. He claims to be a tobacco industry heir who’s renouncing the family business in favor of pursuing his big, philanthropic dream: To provide wireless access to the developing world.

He pitches the business with a smorgasbord of virtuous-sounding tech mumbo-jumbo (“satellites,” “need to get in early,” “have to review the prospectus,” “WiFi for African schoolchildren”) and utter charmlessness of an inexperienced car salesman who already met his monthly quota and is about to clock out for the day. Investors, he says, will “triple their money by the end of the summer.” Somehow, with nothing more than an elevator pitch and the implicit trust of one of the city’s most powerful families, he manages to scam dozens of people out of millions of dollars in the span of a few days.

It takes a generous suspension of disbelief to fully enjoy any frothy teen drama. But when this storyline aired in 2009, it felt above and beyond in its absurdity. There’s no way a random dude with no real credentials, a bad haircut and the personality of a stale slice of Wonder Bread could convince a bunch of millionaires to hand over their money without so much as proof of an actual business plan................ right!?!? But, according to every high-profile scam of the past 18 months, it actually is that easy. It wasn’t an unlikely plot. It was just ten years ahead of its time.

Watching Armie fumble his way through his four-episode arc made me feel exactly the same way I felt watching the Fyre Festival and Theranos documentaries, a sentiment best described as “SERIOUSLY?! THAT GUY?!!!!??? HOW???!!!!” But if there’s one thing I’ve learned from all of this, it’s that no matter what your overall vibe is, if you believe in yourself and have access to people with cash and decision-making power, you can pull off anything.

The sexy, charm-filled, Hollywood con artists of Catch Me If You Can and Heartbreakers were way off the mark. Real scammers have bad hair and no sense of style or humor. They’re awkward and a little shifty. Years before his career-shifting turn as the Winklevii in The Social Network and almost a decade before he finally figured out that a leaner, scruffier look worked way better for him in Call Me By Your Name, Armie’s stiff, weirdo delivery predicted the methods and mannerisms of our era’s most entertaining, infuriating figures.

Armie plays Gabriel with the oafy dullard affect of a Billy MacFarland. He has a vague, Elizabeth Holmes-ian vision of improving the world with technology that doesn’t exist. His chosen targets (rich people, people who are desperate to prove they can fit in with rich people, people who work for rich people) are pure Anna Sorokin (née Delvey.) There’s even a touch of Operation Varsity Blues woven into the story: When Lily van der Woodsen finds out that Rufus Humphrey invested Dan’s college fund in Gabriel’s venture, she sets up a mini reverse-scam of her own and starts paying him “dividends” on the investment from her own account to ensure that he has all the Yale cash he’ll ever need.

Now, in a world where high profile scammers litter the cultural landscape like FEMA tents on a gravelly stretch of Great Exuma Island, going back and watching everything play out (Season 2, episodes 20-23, they’re on Netflix) feels downright uncanny. I highly recommend it.