Cristin Milioti: ‘I slapped the hell out of Leonardo DiCaprio for 12 hours’

The star of ‘How I Met Your Mother’ and ‘Palm Springs’ talks to Ellie Harrison about her ‘once-in-a-lifetime experience’ on ‘The Wolf of Wall Street’, how we are too obsessed with reboots and nostalgia, and her new show ‘The Resort’

‘I am drawn to things that are weird and spiky’ (Getty Images)

Cristin Milioti likes things “f***ed up”. At least, that’s what Andy Samberg, her co-star in the 2020 time-loop romcom Palm Springs, told The New York Times. In that film, Milioti’s wedding guest, Sarah, dies over and over again, in a variety of grisly ways, but still wakes up at the dawn of each new day. In Black Mirror’s award-winning “USS Callister” episode, her digital clone, Nanette, gets stuck in a depraved virtual universe. And her new show, The Resort, sees her holidaymaker, Emma, becoming transfixed by a missing persons case featuring beheaded iguanas and a man whose memories leak out of his ears and bottom.

“I am drawn to things that are weird and spiky,” the 36-year-old actor says. “I like things that tread a very fine line. The Coen Brothers’ whole catalogue was deeply seminal to me. Their movies are so twisted. They make you laugh at things that you’re shocked you’re laughing at. They’re also very moving. And eerie. And they’re beautiful. So I don’t like things in perfect little packages. I like getting into like the nitty-gritty of the challenges of being a human on the planet. Because why wouldn’t I?”

Milioti is talking to me over video call from a hotel room in Los Angeles. It’s morning there, and her hair is tied in a haphazard ponytail, dark brown bangs nestled above pool-sized eyes. Her baggy tee bears a picture of a howling wolf and her knees, clad in tie-dye leggings, are pulled up to her chin. She’s in LA for the premiere of The Resort, but she’s much more at home in New York, where she’s lived for 18 years. “The only time I’ve ever liked staying in LA is when there was the shutdown,” she says. “I don’t do great here. I find it very isolating. And I think it has its priorities out of whack… sometimes the energy of this town seems so rooted in status and trophies. It makes me uncomfortable.” She’s planning on being a New Yorker for life. “For sure, there’s no doubt my mind,” she says. “Life is long and crazy, but I would be shocked if I didn’t live there.”

New York, after all, has been good to Milioti. She’s had a busy career on and off-Broadway, winning a Grammy – and receiving a Tony nod – for her leading role as a flower seller who falls in love with a Dublin busker in the hit musical Once. That show was based on the film that came out in 2007, at a point when Milioti had just dropped out of her acting course at New York University to find work. She also starred in the Brooklyn-set satire Stunning, the futuristic drama After the Blast, and played PA-to-an-alien Elly in the David Bowie musical Lazarus. It was first performed at the end of 2015, making Milioti one of the last people to work with him before his death from liver cancer in January 2016 (he had kept his illness a secret for months). “Working with Bowie was as mind-blowing as you can imagine,” she says. “One of the most beautiful parts of that experience was that I got to sing ‘Changes’ in that show, which is one of my favourite Bowie songs, and it was wild. It was incredible to sing that song for him and to explore his brain and to be a part of something that was extremely meaningful to him in a time of his life that was... I don’t know how to describe it. I can only imagine what he was going through at that time. He was incredibly lovely and kind and invested. It was a real honour.”

In 2013, while Once was enjoying its three-year run on Broadway, Milioti also appeared in a little film called The Wolf of Wall Street. She played Teresa Petrillo, the first wife (and voice of reason) of Leonardo DiCaprio’s quaalude-popping stockbroker Jordan Belfort. “I spent so much of that experience being so terrified of messing it up,” says Milioti, sipping on, in her own words, “the tiniest can of sparkling water you’ve ever seen” from the minibar. “I’d never been on a movie set that big. It was a once-in-a-lifetime experience. I wish I had taken it in more and let go more. But if I had fully taken it in, I would have blacked out. I don’t think my brain was even computing.”

For much of the film, Teresa is the supportive, patient wife. She’s the one who shows Jordan a newspaper ad looking for brokers, she’s the one who encourages him to target rich investors rather than unsuspecting poor clients, and she’s the one who stands by as he flirts outrageously with Margot Robbie’s Naomi Lapaglia at a Hamptons beach party. But later, when she discovers Jordan is cheating on her with Naomi (she catches him snorting cocaine off her breasts in a limousine), she finally snaps. Hitting Jordan repeatedly, she asks him if he loves his new mistress.

“That was a wild night,” says Milioti. “We shot from 8pm to 8am and we did that scene over and over and over.” Did she ever accidentally catch DiCaprio’s face with her hand? “I did, a bunch of times,” she says, eyes widening. “I just kind of slapped the hell out of him for 12 hours. I always had a real attachment to that scene, because you get to see this character, who has swallowed a lot of her feelings down, really get to let loose.” The scene was shot outside Trump Tower, and yes, he did make an appearance. “Ugh,” sighs Milioti. “He crashed the set and he was a complete and utter buffoon, as we all know.” She doesn’t want to give him any more airtime than that.

Before it all went south: Milioti and DiCaprio in ‘The Wolf of Wall Street’ (Appian Way/Paramount/Kobal/Shutterstock)

2013 was a big year for Milioti. It was also the year she joined the cast of the long-running sitcom How I Met Your Mother, shown in the UK on E4, as the mother herself, Tracy McConnell. Fans adored her, but were incensed when, in the show’s final ever episode, it turned out that the woman whom viewers had been waiting to meet for nine seasons had actually died six years earlier. “I had never seen the show when I signed on to it, which was a huge blessing because I didn’t understand the pressure that was behind that reveal. Like, I truly had no idea,” says Milioti. “It was definitely helpful for me to not fully know how long people had waited to meet that character.” She also wasn’t on any social media at the time, which she says was a relief. “I was isolated from it in a way. I know there was a very strong reaction, but I never looked into it.”

Her character in The Resort, Emma, is a world away from the endlessly enthusiastic Tracy. Tracy is an optimist. She believes in soulmates. She’s in a band called Superfreakonomics. Emma, meanwhile, is a cynic. She’s fed up. She’s lost. She’s a woman who, on the first night of her holiday in Cancun with her husband of 10 years, swigs prosecco in a hot tub alone and types “how do I know if I should leave my relationship?” into Google. While her partner Noah (William Jackson Harper) is perfectly happy to plod along, she’s looking for something more. So when she falls off a quadbike in the jungle and finds the phone of a college student who went missing 15 years ago, she becomes obsessed with the case – the only thing that makes her feel alive. Milioti thrives in this sort of role: mercurial, skittish, eccentric. What ensues is a relationship drama with a thriller, a mystery and a comedy thrown in. The two go off on tequila-fuelled searches for clues and make for a goofy but surprisingly successful pair of detectives.

The unhappy couple: Milioti and Jackson Harper in ‘The Resort’ (Peacock)

The Resort sees Milioti reunite with Palm Springs writer Andy Siara. Like that film, the show deals with the construct of time. Emma is struggling to live in the present, and is fixated on a historic cold case. “Someone once told me that a different term for nostalgia is time sickness,” says Milioti. “You feel, like, an actual sickness and an aching to go back to a different time. That really resonated with me. Emma would so much rather be anywhere than where she is. She’s just so desperate to go back in time to where life was lighter, and there were more doors open and more possibilities, and she was more herself. That’s why she becomes obsessed with the disappearance of these two young people.”

Milioti sees nostalgia everywhere in modern society. “Maybe this is just because I’m getting older,” she says, “but it does feel like, as a culture right now, we are so specifically obsessed with nostalgia. Especially in the entertainment industry, where you’re condemned if you age and people are obsessed with rebooting things. It’s like, ‘What if we just rebooted that thing that we all loved when we were 12? Or when we were 20? Or when the world didn’t feel as deeply dark as it does now?’ It’s this thing of wanting to stop time, and wanting to time travel, and wanting to get back to some imagined former self, or something. I think nostalgia can be really, really dangerous. And actually, when I started talking with Andy about this project, he would always say the show is about the toxicity of nostalgia.”

Milioti in ‘How I Met Your Mother’ (CBS)

Milioti admits that she, like Emma, is very preoccupied with the passing of time. “When I was younger, time wasn’t passing quickly enough,” she says. “I would obsess about like, well, when will I be able to do this? When will I have my own apartment or, you know, insert whatever, here, in this blank. But now that I’m older, it feels like there’s not enough time. The most valuable thing outside of your health that you could have is time. And there is just not enough of it.”

She shakes it off, laughing. “I do spend a lot of energy thinking about what I want to do with my very brief time on this planet,” she says. “It’s so finite.”

‘The Resort’ is available from 29 July on Peacock exclusively on Sky and NOW, with new episodes dropping weekly