A candid conversation with the ‘Palm Springs’ star on endless days, existential funks, pirate hooks, Michael Keaton, and the art of “dealing with your shit”
If you want to get a sense of who Cristin Milioti is, ask her about the hook.
“Wait, so you heard about the hook?!” she says, eyes widening as she doubles over laughing on her couch. Actually, it’s technically not her couch; she’s staying at a friend’s house in L.A.’s Los Feliz neighborhood, sort of stuck in between places. She had been filming out in California when the state, the country, and the world at large went into lockdown mode. Luckily, Milioti had a place to crash and her “silent-film, Muppet, trash-can dog,” Rupert, was with her, so all’s as well as it can be in the early summer of 2020, which is not very well at all.
But back to the hook. Both her Palm Springs director, Max Barbakow, and her co-star Andy Samberg have mentioned an incident involving the actress and some sort of implement; and given her reaction, you get the sense there’s a story here. “Well, yes, there is,” Milioti admits with a sideways smile on her face, as Rupert, the silent-film, Muppet, trash-can dog stops pawing at the edges of her extremely oversize tie-dye T-shirt before exiting the frame of the Zoom call. “But then we’d have to talk about the pirate costume, which means we’d get into the whole crazy montage thing, and, well…” she trails off, before comically adding in a Broadway diva’s voice, “Are we inching into spoiler ter-ri-tor-y?”
Yes, we are. It’s been almost six months since Palm Springs, the comedy that she’s promoting in the middle of pandemic limbo, premiered at the Sundance Film Festival, back when you could safely have a film festival, and ended up walking away with massive word-of-mouth buzz and a deal worth $17.5 million and 69 cents. (The 69 cents is key — it officially put Palm Springs over the top enough to make it the biggest sale to ever come out of the festival.) And when we talk in the middle of June, this movie about a cynical maid of honor (Milioti) and a charmingly goofy guest (Samberg) who meet-cute at her sister’s wedding is still a little ways from its July 10th streaming premiere on Hulu. Consider this your official spoiler-alert warning. If you’re one of the legions of folks who watched the movie over the weekend, then you know the deal. If you haven’t seen it yet (and were lucky enough to avoid the slightly oversharing trailer), you may want to check back in later. Everyone from the film’s creators to those first fest audiences have been a little protective about the left turn this film takes.
Which, as many delighted viewers now know, is the fact that Milioti’s character, Sarah, follows Samberg’s character, Nyles, into a cave in the middle of the desert. There’s a flash, and a whoosh, and a fade to black. When she wakes up, she discovers that it’s once again the morning of the hellish day she’s just endured. In fact, Sarah is now doomed to relive and repeat this 24-hour stretch alongside Nyles — who, we find out, has been stuck doing this for a long, long time — ad infinitum. Initially, she’s enraged. Then, a certain fuck-it attitude kicks in, which leads to the duo taking advantage of doing whatever you’d want courtesy of a perpetual reset button. Planes are stolen and crashed. Biker bars become the scene of ridiculous Eighties style dance-offs. One of the now-endless matrimonial ceremonies is suddenly interrupted by Samberg finding a pre-planted bomb in the middle of the cake and shooting the device, via crossbow, into the sky.
Since that last vignette required her co-star to become a makeshift James Bond and the script merely said her character was his archenemy, Milioti wanted to ensure that he had a proper D.I.Y. Bond-worthy nemesis to greet him on the day they shot the set piece. “The challenge became: ‘What’s the most absurd villain I can come up with where she’d only have access to what’s at the wedding, or maybe a CVS down the street?” she says. “I asked the wardrobe department, ‘Can you get me the shittiest eye patch and Captain Hook hand that you can get at a Duane Reade?’ That was what we came up with. And I wanted to keep it a secret so Andy wouldn’t see it coming. I wanted too see him react, then see how I reacted to his reactions in the moment…” She begins giggling uncontrollably. “It’s possibly my favorite scene I’ve ever filmed.”
Except Milioti wasn’t quite done with the hook yet. A little later in Palm Springs’ 21-day shoot, she and Samberg were set to film what would be the most dramatic scene in the film: After having hedonistically enjoyed hundreds of variations of that single summer day together, Sarah and Nyles sit by a campfire and finally talk about their respective pasts. “It was the one sequence we had allotted the most time in the schedule for,” Samberg says, in a separate phone call. “It’s 3 a.m., there had just been a sandstorm, and it’s freezing cold. Everyone’s tired and a little tense. We both had blankets over our legs, and we’re really going deep into the scene … and then, out of the corner of my eye, I see this cheap-ass plastic hook…”
“I’d asked the prop department to sneak the hook to me right before we started shooting,” Miloti remembers. “And in the middle of one of his speeches, I slowly, slowly, slooowwwly pulled the hook out from under the blanket when I thought he wasn’t looking, and just … gently … caressed … his face with it. I didn’t want him to see it. I wanted him to feel it first.”
Samberg claims that he started laughing so hard that it ruined the shot. (“What can I say? I got Clooneyed by her,” he says, referring to George Clooney’s penchant for on-set pranks.) Barbakow later confirms, however, that part of the take made it in the finished version. He also thinks even though you don’t see the hook, the impromptu addition added a level of spontaneity to the scene that helped sell it. “The one thing Cristin kept putting her foot down on was that the performances and the intimate moments had to be respected,” he says. “But she’s also mischievous as hell. And that combination was what made her absolutely perfect for what we were going for.”
“We both like a little fucked-upped-ness in our comedy,” Samberg says. “And the more weird and edgy and fucked up it got, the more she was willing to play with it. I think that’s a big part of her personality … and I don’t think she had been afforded a lot of opportunities to go there in her career.”
When Milioti first got the script for Palm Springs, she instantly recognized that it was part of a subgenre she calls “time-loop comedies” — a category that includes the Mt. Everest-like peak of Groundhog’s Day and the recent boho New York-centric spin on the concept (and personal Milioti favorite) Russian Doll. She dug the humor, the way it tweaked the same-day-times-infinity premise, and the eventual detour into pathos when Sarah decides she’s going to find a way out of this situation or die trying. But what struck Milioti the most was the fact that this project was coming to her at the exact same moment that she felt stuck in a bit of a rut. “I was at a point where I was questioning a lot of things,” she says. “Personal things. Professional things. Without totally lifting up all of my covers, I felt like I was running away from a lot. I was trying to escape certain things, and there was a lot in my life I didn’t really want to look at.
“So I’m reading through it and laughing,” she continues, “and then I got to the end and went, ‘OK, wow, this is a pretty Zen fucking movie.’ Like, it’s weird and crazy, and there’s a whole montage in the middle that’s just bananas — and I love that type of stuff! But it also felt like this examination of what it’s like to finally have to come to terms with your shit. I found myself thinking, you know, maybe being stuck in a time loop isn’t that different from having to face up to things you don’t like about yourself. We all have these moments, especially in adulthood, when we think Why is nothing changing? Why am I making the same mistake over and over again? And that was when” — she switches into a voice that might be best described as caffeinated morning-show radio DJ — “this wacky, kooky wedding comedy turned into something that suddenly felt incredibly relevant to what I was going through.”
It was also one of the very few times that Milioti felt that a potential project actually “got” her sensibility — a sensation, she readily admits, that she’s found in the theater but rarely felt in her two decades as a working screen actor. Growing up in New Jersey, Milioti discovered a love of performing in high school, doing double duty as a theater geek and a singer in jazz and rock bands. When she enrolled in NYU, however, she quickly found herself bumping up against a preordained sense of what she should and shouldn’t be doing.
“There was this desire to, for a lack of a better word, pigeonhole me from day one,” she says. “I’ve always wanted to do odd, offbeat, dark things … I’ve always wanted to play characters, and they were always telling me I couldn’t. That I would never get cast in anything like that. Or that when I sang, they’d tell me, ‘Your voice doesn’t really sound like it belongs in musicals. You should change it. Make it sound like the kind of voice that people wanna hear people on Broadway sing like.’ I just started mimicking anyone who I thought people liked. I found myself consciously trying to imitate Sutton Foster whenever I had to sing something — and Sutton Foster has a gorgeous voice! But I don’t sound like her. At all.
“What they were teaching me, whether they meant to or not,” Milioti says, “was essentially: ‘You aren’t enough. Try and be these other things, or you will fail.’ Because I couldn’t quite fit into those molds. A lot of people in the industry encounter this, but especially women. You’re asked to fit into this one specific thing, and if you can’t do that, no one knows what to do with you.”
She noticed this happening even more once she started trying to book professional gigs after she dropped out of NYU. (“I was a hotheaded 19-year-old from New Jersey, so of course my attitude toward them was ultimately: Go fuck yourself. I’m out.”) Milioti had fallen in with the off-off-Broadway black-box theater crowd, who were doing the sort of deeper, more deranged stuff that made her feel creatively alive onstage. Then she would find herself going out for “all of these CW shows” that she knew she wasn’t right for — but that she chased anyway, “because really, I just wanted to work” — and felt as if she’d kept reliving the same horrible don’t-call-us-we’ll-call-you audition over and over again. Even when she did book an occasional plum gig, like a guest shot on The Sopranos, the experience often ranged from negative to downright nightmarish. (See: her description of having to parade in front of a lot of male cast and crew members in her underwear for her part on the HBO show in a recent Vulture interview.)
Earlier in her career, she remembers an agent, who was very interested in bringing her on as a client, taking her out to brunch. He asked her: Whose career would you like to emulate? “And the first name out of my mouth was, ‘Michael Keaton!’ And he goes, ‘No, no, I mean, a woman! A woman’s career.’ And it was like, well, listen, I could name you tons of women whose work I love! But that wasn’t what you asked me. I want to be Beetlejuice. I want to be Batman. I want to be Birdman! You know what? I probably have a Multiplicity in me, too! It was this repeat of, ‘That thing you want?’ We’re not going to give that to you.”
But, Milioti says, she also recalls another conversation a few years after that ended up being a bigger influence on her career aspirations. “There was this casting agent named Meg Simon, who was always having me read for things,” she says. “One day, I’m going over some pages with her, and she just shut off the video. She said, ‘I come and see you in all this weird off-Broadway shit that you do — it’s why I keep bringing you in. And every time you come in here, Cristin, you just give me some Blake Lively impression!’
“She just point-blank told me, ‘Stop all of that,’” Milioti adds. “’I want to see what you can do, not what you think you should be.’ For an actor who feels like she’s just doing everything wrong to hear that is … it was so helpful. Hugely helpful. It was this earth-shattering epiphany for me because it reminded me, right, there’s a reason I chose to do this. It’s not about booking a sitcom.”
Milioti would eventually end up booking bit parts on sitcoms, showing up on series like 30 Rock (she’s the cartoonishly sexpot comedian with the baby doll voice) and becoming the face of the mythic “mother” in the popular TV show How I Met Your Mother. There was also A to Z, a high-concept must-see NBC romcom starring Milioti and Superstore’s Ben Feldman that folded after one season. But mostly, the New Jersey kid with the fuck-you attitude stopped trying to be someone else and just followed her bliss. She did theater, ranging from dystopian dramas like After the Blast to the Broadway adaptation of the movie Once to David Bowie’s avant-musical eulogy Lazarus. (“How do you take notes on singing ‘Changes’ from the man who wrote ‘Changes’? With an open heart and a fucking shit-eating grin, because it’s David Fucking Bowie!”) She performed shows at Joe’s Pub and collaborated with the R&B singer/producer Boots and Run the Jewels on a song called “Delete Delete”; that’s her singing the hook, which she also wrote. She racked up small but memorable supporting roles in The Wolf of Wall Street and the standout second season of Fargo.
But it was her part in the now classic Black Mirror episode “USS Callister,” in which Milioti becomes trapped in a toxic fan’s sci-fi fantasy and turns the tables on him, that upped her “who’s that actor?!” status. It was also the role that prompted Samberg and Becky Sloviter, the head of production for the Lonely Island’s production company Party Over Here, to call her in for an informal sit-down. “It was what we call a ‘general meeting,'” Samberg explains. “A sort of introduction to talk about maybe working on something in the future. I happen to be in the office that day, so I swung by to say hi. I was just going to pop in for 10 minutes. Three hours later, we were still talking and laughing. You could just sense a rapport there.” When the Palm Springs script came across their desks a few weeks later, he said, they both immediately went ‘Milioti.’
From there, it was all over but the shouting — and the whirlwind 21-day shoot and crazy pirate costumes and biker-bar dance rehearsals. (Milioti and Samberg bonded during those awkward choreography sessions, she admits, “because nothing allows you to get to know someone quicker than being in the foxholes of idiocy together. Also, The Foxholes of Idiocy: My Life in Entertainment would be a great name for my memoir.”) “It wasn’t until Andy [Siara, Palm Springs‘ screenwriter] and I heard Cristin and Samberg trading lines that we thought, ‘Oh, this is going to work,'” Barbakow says. “And it was also immediately apparent, after you heard the choices Cristin was making, that she would be the emotional catalyst of the movie as well. We realized: ‘Oh, this is her story.'”
Milioti, for her part, felt vindicated. Not because Palm Springs had given her a lead role, or that it confirms that she may be the 21st century’s best screwball comedian, or the fact it could possibly be the sort of high-profile summer-movie hit that nudges her inches closer to an ever-shrinking A list. It’s because, she says, it proved that the sort of fully formed, highly flawed “characters” she had wanted to play way back when she was starting out, the ones that professors and agents and people who kept continually telling her “no” said she would never get? It felt like there was a place for her to play them onscreen now. The refusal to let herself be easily categorized — to remain, as she calls it, “genreless” when everybody was telling her to brand herself as this type, or that flavor-of-the-month clone — had paid off. Milioti may finally be getting her Michael Keaton 2.0 moment.
“I like that you see that Sarah is inherently a good person,” she says near the end of our conversation. “But I really like that you get to see that this is someone who’s made horrible choices, that’s dealing with some issues, that has to go through a journey of acceptance to get on the other side of things. You get the sense that this woman has never listened to herself — and when you don’t listen to yourself, you do a lot of fucked-up shit. I loved that the movie made room for all of that. You get to see the good, the bad, and the ugly with her. And I was very interested in the ugly.”
Now, Milioti says, exhaling loudly, she’s trying to borrow a few pages out of her character’s playbook. She’s been using this time being stuck in one place to untangle her own self-admitted fucked-up shit. When we talk, Black Lives Matter protests are still going strong throughout the nation, and Milioti has been masking up and marching as much as she can. But she’s also been reading up on the larger social structures and attitudes in an attempt to educate herself on her own part in all of it; Robin DiAngelo’s White Fragility has not only opened her eyes but set her tunneling down a recommended-reading rabbit hole. She beats herself up about not being more cognizant about these things sooner, then sees what can be done to make up for lost time. Daily calls are being made to senators, which is something she might not have had time to do if she’d been on a set right now. Should you be curious about the ways in which author/podcast host Brené Brown’s thoughts about shame extend past the personal, Milioti is happy to share her thoughts. When it’s suggested that a question is threatening to turn the interview into an extended therapy session, her gleeful reply is: “Why the fuck not turn this into one?”
She wants people to enjoy Palm Springs, and she wants them to see her work “because, let’s face it, that’s what every performer wants,” and now, most of all, she wants to use this rinse-repeat nightmare we call 2020 to emerge as a better, kinder, more generous person — to both others and herself. “It’s an eerily prescient movie,” Milioti says, “because who doesn’t feel like they’re waking up and reliving the same experience over and over right now? But it also reminds you that the question, really, is, what can you do with that time you’ve got?” Then she says goodbye, setting off to see what the rest of her day brings. So long as it’s different from yesterday, she feels like it’s all gonna be A-OK.
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