Courtesy of IFC Films. An IFC Films release.Pretty Problems, a comedy from IFC Films and directed by Kestrin Pantera, is now showing in theaters and available on video on demand.
In Pretty Problems, a couple discovers that being in the 1% does not 100% guarantee happiness.
Lindsay (Britt Rentschler) works at a consignment boutique. Her husband, Jack (Michael Tennant), is a disbarred lawyer working as a door-to-door salesman. They both desire more out of their lives, their careers and their marriage. They’ll soon learn to be careful what they wish for.
One day at work, Lindsay meets eccentric bon vivant Kat Flax (J.J. Nolan), who, despite having just met her, invites Lindsay to a weekend getaway at her home in Sonoma’s wine country. Lindsay digs Kat’s vibe and lifestyle — and Kat bought a ton of clothes — so Lindsay accepts the invitation. Jack, who thinks this whole thing is weird and potentially setting them up to be murdered or indoctrinated into a sex cult, grudgingly agrees to come along.
Kat and billionaire husband Matt Flax (Graham Outerbridge) welcome them to a lavish home with a spectacular view of vineyards and lots of unusual art (“This man is made of dicks!” Jack notices of a statue).
Also sharing the weekend are Matt’s friend, Kerry (Alex Klein), and his girlfriend of the moment, Carrie (Charlotte Ubben), who says she’s model/actress/dancer so much that it has become true in her mind.
Over the weekend, Lindsay and Jack embark on a wild, drug- and alcohol-fueled odyssey of uncomfortable conversations, unconstrained karaoke, Roaring ’20s murder-mystery role-playing parties, unexpected reunions with former sex partners, spirit-cleansing shamanic rituals and a whole lot of awkward economic disparity that will put their marriage, and their images of themselves and each other, to the ultimate test.
Rentschler, who is also a writer and producer on the film, took us inside the humor, the characters and the moments of inspiration that make Pretty Problems a comic destination well worth the trip.
Let’s Just See What Happens
Rentschler says that Pretty Problems got its spark from longtime friend Tennant. “We were at his birthday dinner, and he kind of had this weird look on his face,” she says. “And the next day, he called me and was like, “You know what? I think we need to make a movie. And I think we need to do it with just our friends. We’re not going to hire celebrities. We’re not going to try to produce something on a huge scale. We’re going to write it for our people. We’re going to make it with our people. And then let’s just see what happens. Let’s see if we can do it that way.”
Sonoma Is The New Napa
Set mostly in California’s Sonoma Valley, Pretty Problems was a hit at the Sonoma International Film Festival, where it won the Jury Award for Best English Language Feature Film. Jokes like Sonoma being “the new Napa” definitely played to the crowd. “That joke has never paid off better!” Rentschler says. “It was such a thrill. It was so cool to see the house packed, and then by our second showing, they were turning people away at the door. It was unbelievable, and it was so cool to see people who are from that region come out and enjoy all those jokes about their homeland.” That includes poking fun at the area’s spotty cellphone coverage and its snooty sommeliers (Tom Detrinis delights as biodynamic wine purveyor Georges, who says that “market price” is whatever he’s feeling at the moment).
Luxury On A Budget
The characters might drive a $100,000 Tesla with $150,000 of wine in the back seat, but Pretty Problems had more of a Toyota Corolla and a case of Corona production budget. Rentschler says they took the work-with-what-you-have mindset of indie filmmaking to bring the world of outrageous excess to life. “We were able to borrow this house. This family was incredible,” she says. “They were going to be at one of their other properties during the time that we were shooting. They let us come in. They let us shoot. And everything that we found was there. We just kind of rearranged it.”
In fact, Rentschler says that anyone can be a patron of independent cinema just by letting a filmmaker borrow their stuff. “If you have a car, if you have a store, if you own a restaurant, if you have a vacation home, and an indie filmmaker asks you if they can borrow it, please say yes. It can really be the difference between something getting made and something not getting made.”
Go Grab Dick Imagery!
So that house really came included with all the penis art? “Oh, baby! We even held back! We held back on that,” Rentschler laughs. “We had two cameras operating so that we could get as much footage as possible in our days because we had such a limited amount of time. Whenever it was just a single A-cam shot, Kestrin’s like, “B-cam! Go grab dick imagery!” We’d be like running around the house. We had such a good time. There was just so much phallic art.”
Vape ’Em If You Got ’Em
You’ll notice that Kat always has a vape pen at the ready, and discerning eyes will notice that every pen complements Kat’s wardrobe. It was an element of Kat’s character that was born from a serendipitous moment with Nolan. “It was actually [J.J.’s] idea!” Rentschler says. “It was one of those brilliant moments where, as a producer, as a writer, you do as much as you can to create the world and have your vision, and then you invite other people in — and they’re such brilliant creatives in their own right. They add things that you never even knew could be there. She came in on the very first night, and she pulled a vape out of her cowboy boot and she hit it. And Michael and I looked at each other and were like, “Oh, shit. This is perfect.” And J.J. was like, “Oh! What if Kat vaped? Can I go buy a vape that matches every single one of my outfits?” And we said, “Yeah! You absolutely can.” Nolan went out and purchased about 15 vape pens. It was a worthwhile expenditure.
Savage, Bro!
Kerry lives a life of carefree opulence and rigorous body-image maintenance. He’s beneficiary of his grandfather’s inventing the tater tot during World War II. Kerry’s a dim but likable playboy played by Klein, who is married to Rentschler. “What I really love about what he did with Kerry, is that he didn’t just keep the meme part of it,” she says of her husband’s role. “He mixed his own sweetness in with this guy, and that’s why it ended up being so much more unique than your normal stereotype of a trust fund bro.”
Not Your Grandmother’s Bingo
In an early scene, Jack is trudging from house to house, making his solar-panel pitch to anyone who’ll open the door. One such man mistakes Jack as being the guy from “Tittie Bingo.” Wary of Googling “Tittie Bingo” at work, I asked Rentschler about it. “Tittie Bingo is a real thing!” she says. “It happens in Austin, and you gotta go to Austin to find out. Get thee to SXSW!” Of course, Pretty Problems won the Audience Award at SXSW 2022.
Oh, God. I Want A Milton.
Throughout the film, there are mentions of a mysterious entity named Milton who seemingly grants wishes and pulls all sorts of strings behind the scenes to make stuff happen. Milton is a force of pure benevolence, and I want one. “Oh, God. I know,” Rentschler sighs. “If we ever find out where you can order a Milton, I will let you know.”
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