When Cristin Milioti found out she had been cast in The Penguin, she was on a black sand beach in Iceland, about to mount a horse. It was a few days after she had taken part in a chemistry read with co-star Colin Farrell, and word came via text. “I put my phone away and then I got on one of those incredible little horses that they have there, the special Icelandic horses, and I galloped on a black sand beach and giggled and cried,” Milioti tells me from her home in New York. “It was amazing. It was ecstasy, to be able to take that in and then be in a place that is so big and expansive and spiritual.”

It’s a late morning at the tail end of August, and Milioti has returned from a sojourn in LA “very very very” early that morning. As such, she’s sitting in her pajamas, a far cry from the gothic high glamour demonstrated in The Penguin, the HBO limited series spin-off of 2022’s The Batman, in which she stars alongside Colin Farrell [who embodies eponymous Penguin/Oz Cobb, rendered unrecognizable in prosthetics]. The show centers around Cobb, a disciple of the Falcone crime family who goes rogue in an attempt to seize power of the drug trade in Gotham. Milioti meanwhile portrays Sofia Falcone, the cast-aside daughter of the Falcone clan who’s discovered a new euphoric drug called “bliss,” and Cobb’s ally-turned-nemesis.

Milioti’s Falcone oscillates between a cool-as-a-cucumber, cigarette-wielding sartorialist and an unhinged killer. But although she’s decidedly the villain, The Penguin’s writing is layered, and Falcone’s behavior, as it unfolds, is the result of a lifetime of lies and condescension at the hands of her morally bankrupt father and a stint in a corrupt mental health facility. Though the show is a high-stakes spin-off of a DC comic, Milioti’s performance needles at a universal truth: she delivers a relatable portrayal of sexist gaslighting, a woman’s autonomy obliterated by the “crazy woman” trope. “I think it’s not an uncommon experience as a woman in the world to feel like you’re being gaslit by, you know, society,” says Milioti. “There are innumerable instances throughout history, forever, of women being lied to and punished. It was sort of thrilling to get to portray that, but also get to portray her seeking revenge.”

In the show’s fourth episode, Falcone’s story reaches a crescendo. Pushed to her limits, she opens the gas valve of the Falcone mansion as her family slumbers. A particularly cinematic moment (and one that Milioti references in conversation), sees her don a gas mask as she saunters around the house checking on the bodies, her silk dress shimmying as she skips, eerily scored by jazz classic “So Long, My Love.” It’s a pivotal moment in the character’s development: her wardrobe graduates from muted blacks to exuberant silks, her simple makeup is rendered charcoal and experimental, and her usually pinned-back black hair is unkempt, falling around her face. 

“It was so thrilling to get to that fourth episode,” Milioti considers. “She becomes so much more physically free…what she wears, it’s looser, it’s louder. You know, she really gets to breathe for the first time.” It’s in that episode that—after being interrupted by her one remaining male family member, she puts a bullet in his head—thus gaining the respect of the mob’s henchmen. It was a scene that resonated with the show’s female audience, “So many women have stopped me and have referenced that moment in particular. [It’s] thrilling to watch even though it’s obviously morally reprehensible. I feel like that’s sort of one of the many moments that Sofia has that’s a sort of fantasy moment for people who’ve been interrupted,” she says. This kind of unbridled impulsivity was a breath of fresh air for Milioti, who describes herself as a chronic overthinker. “I have never thought of her as crazy, I love her so deeply. But I definitely think of her as unpredictable, which is also so thrilling to play. You know, someone who takes things moment by moment. I’m someone who’s so trapped in my own brain sometimes that it was really wonderful to play someone who operates on instinct.” 

But although The Penguin has undoubtedly been Milioti’s maestro moment (and saw her nominated for an Emmy, a SAG award, a Critic’s Choice Award, and a Golden Globe) it was far from her breakout role. The Italian American actor was cast in The Sopranos at age 21, played Leonardo DiCaprio’s character’s first wife in The Wolf of Wall Street,  and played time-warped Sarah in 2020’s Critics Choice Award for Best Comedy, Palm Springs, to reel off just a few. 

And although thanks to The Sopranos and The Penguin she’s perfected the Italian American gangster-adjacent character, Milioti’s range is expansive. In How I Met Your Mother, she takes on the cookie-cutter Everygirl, while a cameo in sitcom 30 Rock sees her portray a hyper-sexual bimbo. This scope, Milioti tells me, is far from accidental. “I look for the ability to push myself in a new direction. I really try to take on as many varied things as I can. I like discovering new colors—I guess, for lack of a better term….If it’s similar to something I’ve just done, I try to pivot away,” she explains.

One of these diverse roles was in the musical Once, which follows the story of an Irish musician and Czech immigrant (Milioti), who fall in love by dint of their shared passion for music. In 2011, Milioti was cast in the American Repertory Theatre’s production of the musical, but the show quickly graduated to Off-Broadway, and then, in 2012, to Broadway itself. Milioti was, per Rolling Stone, “a revelation in the part, delivering punchlines with a delightful deadpan and singing the show’s hyper-romantic ballads with passion and intensity.” The production’s album won the Grammy Award for Best Musical Theater Album. 

In 2021, Milioti dusted off her singing chops once again to release a bare-bones cover of Bon Iver’s “715 Creeks.” Does Milioti harbor ambitions to sing professionally again? “Gosh, Yes. I miss it so much. I miss singing so much. I really miss it,” she gushes without hesitation. “I notice such a difference in my countenance when I sing regularly. I did a concert maybe two years ago—I used to do them more often, in New York, and just noticing the two weeks of rehearsal leading up to it. Or you know, sitting with all these women in my apartment working on harmonies—it’s like an instant joy pill. [Evidently, bliss is still heavy on her mind]. I miss it a lot and I’m always trying to keep my eyes peeled for opportunities to get to sing more.… It’s a whole different part of my brain and it’s one that I have to revisit,” she says emphatically, before laughing at her enthusiasm and apologizing for the “long-winded answer.” 

So, what’s next for Hollywood’s hottest new television villain? The actor has recently filmed a pilot for a new TV show Seven Sisters with Elizabeth Olsen, and wrapped filming for a secret project she’s not yet at liberty to discuss. As for reprising her role in another season of The Penguin? “My honest answer is I don’t know. I would love to revisit it, and gosh that would be a dream come true but no one has mentioned anything.” But for now, Milioti is eager to rest. “I think the downtime for the foreseeable future will just be resting for a moment, and experiencing the last days of New York summer.” 

As for her longer term career trajectory? Just as her Sofia Falcone resonated with women who were belittled by the patriarchy, Milioti will be seeking out roles that strike a chord with their audience. “Oftentimes my favorite things to watch reflect my experience of the world, even if actually they’re showing me a whole new different way to look at things. I think that any piece of work that feels like a connection, including connecting over how insane it feels to be alive right now, that’s certainly what I seek out to experience when I watch things or when I read things, and it’s certainly the type of work that I seek out to create as well.” 

Judging by The Penguin’s glowing reception, Milioti’s work will be shaping and reflecting our universal experiences long into the Gotham night, and beyond. 

Photographed by Arnaldo Anaya Lucca

Styled by Anna Katsanis

Written by Juno Kelly

Hair: Tommy Buckett

Makeup: Lisa Aharon 

Flaunt Film: Norman Nelson