‘Pretty Problems’ Contemplates Our Fascination With the Ultra-Wealthy

Less than ten minutes into director Kestrin Pantera’s film Pretty Problems, wannabe fashion designer Lindsay (Britt Rentschler) and her husband Jack (Michael Tennant) have lost phone service in California wine country on their way to a weekend away with absurdly wealthy, brand-new-practically-strangers friends. When they make it to the chic, modern country dwelling of Cat (J.J. Nolan) and Matt (Graham Outerbridge), Jack voices our exact thoughts as he says, “That’s a murder house. That’s a house where murder happens.” While a murder (spoiler) doesn’t occur in this film, it does exhume pointed truths about the ultra-wealthy and our collective obsession with them.

When Pantera listed off her favorite films to me over Zoom–The Social Network, Fight Club, The Royal Tenenbaums, Wayne’s World–it was clear that her deep familiarity with tales of twisted comedic class divisions have perfectly set her up to direct this satire. She also credits her move from California to North Carolina, plus two years spent in Taiwan, as giving her the ability to understand things outside of American ethnocentrism. That perspective shines during the film’s more vulnerable moments, like Lindsay’s earnest desire for more friendships in her lonely adult life and her preoccupation with what her husband isn’t.

Pretty Problems kicks off with Lindsey, who—dissatisfied with her job, marriage, and tax bracket—leaps at the opportunity to become friends with dry-humored, free-spirited, and vape-addicted Cat, who waltzes into her boutique one day insisting that Lindsey join her for a weekend away. The weekend is jam-packed with an itinerary that would make even the most ambitious bachelorette parties seem tame: karaoke, wine tasting, murder mystery night, pool-side massages, a hokey cacao ceremony, and a copious amount of drinking and psychedelics.

Admittedly, there were a couple of times I expected the trope-y characters to fall flat; but the film was often a step ahead of me, harboring more complexity than I credited it for. A kooky rich woman looking for her next little boredom project? That was Cat. But instead being vapid and self-absorbed, a real loneliness and kindness peeked out from underneath her exotic array of headscarves. I was also ready for the finance bros who’ve evolved their substance abuse issues into identities like “sommelier” and “brewery owner,” Matt and Kerry (Alex Klein), to be your basic, stereotypical rich douchebags. And they sort of are—but in a surprisingly touching scene, the two of them kindly welcome Jack into their crew for the weekend.

When I brought that scene up to Pantera, she joked that “a long conversation between guys on a deck sounds like a death sentence.” But her multifaceted approach to comedic directing came into play again. “I always try to empathize with the point of view of every character,” she said. She cited Wayne’s World again, noting that director Penelope Spheeris “did a really good job” creating these “totally empathetic guys.” “With the two douchebag rich guys in our movie,” she said, “they weren’t classically like punk jock jerk guys.” Allowing those human moments to expose themselves elevates what could have easily been a flat farce of a film.

Television and movies are having a field day skewering the ultra-wealthy, and frankly, it’s a theme I will never tire of. Succession, Big Little Lies, and The White Lotus all did it well. But Pretty Problems is less of a takedown of the one percent as it is a critique of our fascination with them. When Jack learns that Cat’s offer to fund Lindsay’s clothing line is as empty as her pockets are full, it’s not because she’s malicious and out to embarrass Lindsay or plans to steal Lindsay’s creative IP—it’s just that she’s just as lonely and flawed as Lindsay. “Lindsay’s isolated because she’s broke, Cat is isolated because she’s rich,” Pantera explained. Unfortunately, the rich really aren’t that different from anyone else.

Pretty Problems releases on Friday October 7th in select theaters and on demand. As for what’s next, Pantera said all she wants to do is “make funny action and sci-fi movies.” The next project she’s hopping on as director has the incredible working title of Spy Sluts. Lindsay and Jack might be lost in the movie, but Pantera certainly is not.