Falling in Love With Cristin Milioti, Again and Again (and Again)

Kevin Fallon
·11 min read
Photo Illustration by Elizabeth Brockway/The Daily Beast/Getty
Photo Illustration by Elizabeth Brockway/The Daily Beast/Getty

No one laughed harder at the 69 joke than Cristin Milioti.

The actress, the mother from How I Met Your Mother and your favorite part of so many projects since, plays the lead in Palm Springs, the mind-melting existential romantic comedy co-starring Andy Samberg and produced by his Lonely Island crew.

Manifesting all the energy from the gasps in the audience after a shocking out-of-the-gate plot twist, the film launched a competitive bidding war after its premiere screening in January at the Sundance Film Festival.

The keen interest was surprising at a renowned indie film festival branded with a certain industry gravitas, where the most expensive film acquisition was for Birth of a Nation, a 2016 movie about Nat Turner’s slave rebellion. (That film was eventually torpedoed by scandal.) This was a 90-minute rom-com from the guys who brought you “Dick in a Box.”

More shocking was the news that came out of those bidding wars. Palm Springs had eclipsed Birth of a Nation’s $17.5 million record by an extra, purposeful 69 cents: $17,500,000.69 to become the biggest Sundance deal in history.

“I know it’s super juvenile humor, but I was screaming when I saw that,” Milioti tells The Daily Beast. “The fact that it was 69 cents is so funny to me, and will always be very funny to me.”

The chef’s kiss to the whole thing was that many of the Hollywood trade publications who report the ins and outs of major Sundance deals were constricted by standards into reporting the figure flatly sans context.

“That’s what’s so funny about the joke,” Milioti says, still laughing just as hard six months later. “Nobody wants to write, ‘By 69 cents, which is of course a joke about a sex position…’ It’s the perfect set up.”

Ahead of Palm Springs’ debut July 10 on Hulu, Milioti is talking by phone from Los Angeles, where the New York-based actress started renting a friend’s house in the scramble for shutdown safety.

Outside of the jarring experience of, after months of isolation, standing shoulder-to-shoulder in solidarity with thousands of people during the Black Lives Matter protests, it’s been just her and her dog, repeating the same day over and over together.

It hits on what’s become, now, the second hugely surprising distinction held by Palm Springs since that initial Sundance premiere: It may be the most eerily timely and resonant film of the coronavirus quarantine era.

For Milioti, who followed up her Tony nomination and Grammy Award for Broadway’s Once with a scene-stealing turn in The Wolf of Wall Street, Palm Strings is her first leading role in a major movie.

It’s also emblematic of everything she’s been trying to do and say with the characters she’s played: Women who are warm, but tough; who treat making mistakes as normal, not messy; who are hopeful and romantic, but don’t surrender themselves in the process; who are afraid and might not be equipped to face those fears, though they try.

If Palm Springs is a rom-com, Sarah is unlike any rom-com heroine you’ve seen.

Most people had their meet-cute with Cristin Milioti seven years ago in the pouring rain. Now they’re going to fall hard for her in the desert.

“Get right with your Lord and govern your own shit…”

Palm Springs takes place at a wedding in, well, you know.

Milioti is Sarah, whose sister is the bride, and for whom there is no wine glass big enough to get through the tedium of the romance pageantry. Intrigued by the borderline unsettling, yet somehow charming, energy of Nyles, another guest played by Samberg, she downs her last fuck to give with her merlot and hooks up with him.

<div class="inline-image__credit">Hulu</div>
Hulu

But then a man charges them in the desert, shoots Nyles with an arrow, and chases him into a glowing cave, through which a horrified and scared Sarah follows. (Cue those aforementioned gasps.) What she learns, much to her chagrin, is that the cave was an entrance into an Infinite Time Loop that traps both her and Nyles, who now will be living the same day at that damn wedding, over and over.

A clever Groundhog Day-esque homage filtered through the Lonely Island lens—which on its own was enough to score a Sundance record—suddenly speaks profoundly to an audience forced by shutdowns and quarantines to confront heady, somewhat terrifying questions about their own lives.

On the one hand, it’s rolling over in the morning and realizing, huh, I guess this is the person I’m stuck with every day, until who knows when. How do I make the best of it? How does that change my relationship with myself? In quarantine, what is time anymore, other than remembering to shower every few days?

On the other, it’s the epic, torturesome battles between yearning and reality: The desire to free oneself from the confines of circumstance, and the crushing truth that, no matter how much you want it, it’s not possible. What then? How do you deal with that?

You could look at Sarah and Nyles as two people forced by fate into each other’s lives, helping the other grapple with their romantic desires and reluctance to commit. Or you could look at them as high-concept versions of all of us. The film isn’t asking what we need from other people, or even from a life outside of an Infinite Time Loop. It’s asking what we need from ourselves.

(It is imperative that this heady discussion be interrupted with a point that cannot be stressed enough: Palm Springs is also very, very funny. Goofy, hilarious, raunchy, surprising, and all of that. But yeah, also...life, man…)

“It’s become eerily relevant for our time, but I thought that it applied to life regardless, because I thought that it was a movie about the inability to escape one’s self,” Milioti says. “You wake up every day with yourself. And like you can try and run, you can try and numb yourself. You can try and distract yourself. But at the end of the day, you just have yourself, and you either have to get right with your Lord and govern your own shit, or you’re going to be really unhappy.”

Of course, she loved the romantic comedy elements, too. But it’s the running theme of talking about this movie: There’s so much Other Big Stuff that’s exciting to discuss.

“I’m afraid it’s going to sound pretentious or something, but it is truly like how I felt when I read it,” she says, through a sort of giggle-apology. “Like yes, absolutely, you’re focused on this romance. But also, I think that we all understand very deeply that feeling of wanting to get away from yourself.”

“I’m a very sexy baby…”

Our first long sit-down with Milioti was back in 2015 when she starred in season two of Fargo, during which we were illuminated to her unorthodox pop-culture education. She was 9 the first time she saw the Fargo film—fully admitting now that this was wholly inappropriate—and considered herself an amateur Coen Brothers scholar by the time she left middle school.

(Milioti once gave a speech at an awards ceremony where she and McDormand were both honored onstage, and delivered a heartfelt tribute to how McDormand’s Fargo performance taught her at age 9 how strong women could be. McDormand tracked Milioti and her father down afterward: “You let her see Fargo when she was 9?!”)

That she’d eventually star in Noah Hawley’s Fargo series on FX is one of the full-circle moments that you can’t script. When you look at Milioti’s career, it resembles a certain kind of rocket launch, a series of big breaks that have propelled the next, all one right after the other, but each circling back with poignant moments like that; an upwards trajectory with a spiraling smoke trail of curlicues.

When she was cast as “Girl” in the Broadway adaptation of Once, a character whose name is supposed to telegraph a blank slate in the musical love story, she was praised for, as The New York Times wrote, turning in a “full-fledged version of what she only threatened to be in the film: a kooky, life-affirming waif who is meant to be irresistible.”

The weekend before the Tony Awards, she was asked to audition for The Wolf of Wall Street. On the Saturday before the ceremony, she had rehearsal for the telecast in the morning and rushed to her screen test before noon, strapping on heels and teasing her hair along the way. She spent Tonys night reveling in her show’s embrace. The next day, nursing a brutal hangover, she got the call that she was cast opposite DiCaprio in her first movie.

And it was after seeing Once that How I Met Your Mother creators Craig Thomas and Carter Bays, who had exhausted practically every TV sitcom actress in Hollywood as a possibility, felt that they finally found the actress to play the show’s most pivotal character. The day after her final performance as Girl, she flew to Los Angeles to shoot her first scene for the show.

All of this, however, can be traced back to her still-memorable first break, playing the woman forever known as the “Sexy Baby” on an episode of 30 Rock.

Fey took a chance casting Milioti, who had then been doing very, very off-Broadway theater work, during the series’ era of A-list guest stars. But she proved pitch-perfect for a complicated role, a spoof of female comics who play up their sexuality, infantilizing themselves to appeal to men. (Hence, “I’m a very sexy baby.”) The gag, of course, was that there was far more to her story than Fey’s Liz Lemon was giving her credit for.

That breakout role is interesting to think about now in the context of Milioti’s Palm Springs performance. You can look at every character she’s created and see the ways in which she’s rebutted tropes of each project’s respective genre: Romantic comedies like A to Z, romantic dramas like Modern Love, sci-fi thrillers like Black Mirror: USS Callister, dark mysteries like Fargo.

It’s as conscious a mission as Milioti has had when mapping out her career. It’s why it’s not surprising to hear that, in her mind, Palm Springs was never a romantic comedy.

“Obviously, that is what this is,” she says. “But I’m always afraid that people equate that term with something that is, like, fluffy.”

It’s fair, especially when applied to Palm Springs. You think of a rom-com leading lady a certain way. Sarah, however, screams things like, “Suck my dick, Officer Bitch!” at a cop, is very specific about the kind of ball hair she wants on her penis tattoo, and, on a more serious level, is clearly battling buried emotional issues.

“I was so excited to be able to play someone who was a full-body human,” she says. “I think that she does some very shady shit, for lack of a better term. And she is in a lot of pain. To me she was not a trope, and I was very, very excited by that.”

It’s her secret weapon to be exactly the kind of actress you might be inclined to cast as a trope, but who refuses to settle for that.

She has those big brown eyes, the ones so many have described as saucer-like (“doe-eyed” is a common one, too). They are so radiant and warm, it’s no wonder that out of every actress in Hollywood, she was the one cast as the woman a guy would take one look at and feel certain she was the person with whom he would want to spend the rest of his life.

But they’re eyes that you look at and can tell are instantly sizing you up, or hiding everything she wants to share, or feeling everything at once. Her characters give you the sense that if you look through those eyes, you’ll have an entirely different way of seeing the world.

It’s understandably hard to articulate because it’s a quality that’s intangible. Hawley did a better job of describing it than perhaps anyone has yet. Speaking at a panel event promoting Fargo, he was asked why he thought of Milioti specifically for the series. Thinking back to all the characters he’d seen her play at that point, he looked at Milioti and delivered a simple answer: “I was rooting for you.”

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