Cristin Milioti Reflects on Her Journey from ‘The Sopranos’ to ‘The Penguin’

Cristin Milioti prefers to keep her personal life private, but she’s found herself discussing it quite a bit recently due to her high-profile roles. Last fall, she gained critical acclaim for portraying Sofia Falcone in HBO’s “The Penguin,” where she starred alongside Colin Farrell’s titular villain from the 2022 blockbuster “The Batman.” This spring, she led the first sequel episode of Netflix’s “Black Mirror” anthology series, titled “USS Callister: Into Infinity.” These projects have garnered a lot of attention and praise, causing Milioti, who is 39 years old, to spend a significant amount of time doing interviews and promotional work for nearly a year.

Milioti finds herself in a tricky predicament due to her experiences. “I’m extremely proud to have been involved in everything, and I want to discuss it,” she shares during a gloomy day in Los Angeles at the Chateau Marmont. “It’s awkward to overthink oneself in a public setting, but it feels uncomfortable even when it’s not public.

She takes a moment, her eyes scanning thoughtfully for the appropriate words. “Clearly, there’s a side of me that enjoys standing on stage and proclaiming, ‘Quiet now, I’m about to sing!’ Yet, this confidence lies in a different realm than introspection.

In a chat, Milioti appears strikingly ordinary: She’s quick to chuckle at herself, eager to forge bonds, and unconcerned with focusing on herself or her acting techniques – even her reluctance towards reviewing her own performances. “I don’t believe it feels authentic,” she admits. “I don’t think we’re designed to encounter ourselves in that manner.” However, when prompted by EbMaster to reminisce about notable moments from her entire career, Milioti wholeheartedly seizes the chance.

The Sopranos (2006–2007)

Director Steve Buscemi cast Milioti in her first on-screen role, as a mob boss’ daughter on Season 6 of one of the most acclaimed TV shows of all time.

I hadn’t watched it due to financial constraints as we didn’t have HBO. To be honest, I was quite anxious because the set was so large and I wasn’t familiar with how they functioned. Had I realized the magnitude of that show, I would have been in a state of anxiety. Steve Buscemi was incredibly kind. It’s easy to feel insignificant amidst such a production, but he made me feel just as important as someone who had been on the show for a long time. At the time, I was on the verge of leaving college due to mounting debt and frustration. The job offer came in, and I thought, “I can now drop out.

30 Rock (2011)

Milioti guest starred as a comedy writer who embodies the over-sexualized and infantilized anti-feminist stereotype of the early 2010s so completely that fans still quote the character’s catchphrase — “I’m a very sexy baby” — back to her.

Among the roles I’ve had the privilege to embody, that one still stands out as a personal favorite. When I walked into that audition, I felt a strong connection and knew exactly how to approach it. I was a huge fan of that show, and getting immersed in its world was an exhilarating experience for me. Since I was already familiar with every set, it felt like stepping into a dream come true. Tina was a significant idol of mine, and she couldn’t have been more gracious. Wearing the same blonde wig as Will Forte’s character in the show, Jenna’s boyfriend, was an exciting bonus that I still recall with enthusiasm.

Once (2011–2013)

Adapted from the beloved 2007 feature film, this Broadway show won the Tony for best musical; Milioti was nominated for best actress for her performance as a Czech musician who falls in love with an Irish busker.

Reflecting on it now, I can say that I must have performed that show more than 500 times. It had an immense impact on me personally, yet it was demanding and exhausting. Each performance required me to play the piano and sing continuously while delivering a deeply moving narrative. There were moments when the atmosphere would shift, people would weep, and I’d feel a profound sense of connection – but performing it 500 times was no small feat. During that time, my life outside the show was minimal. I didn’t socialize or go out, constantly worried about preserving my voice. Looking back, I believe I would handle things differently today. At that time, I was quite young. Now, I think I would strive for a balance – after all, it’s important to live a little and not sacrifice everything for the stage.

The standout tune from that series is “Gold,” which concludes Act One and marks the moment my character acknowledges her love. In this scene, everyone appears to be slow dancing while playing their instruments, a sight that still gives me goosebumps. Later in Act Two, we perform it without musical accompaniment, and every performance, regardless of any challenges faced during the show, was made special by this moment. It was as if the entire audience was united with us. Such a moment is truly empowering.

I deeply yearn for more opportunities to sing. It’s something I truly miss and cherish. Singing offers a unique freedom of expression, yet it can be challenging to find the right song or moment. Given my recent experiences, I’m unsure how singing fits into that narrative, but the desire is there. I long to explore this aspect more.

The Wolf of Wall Street (2013)

Martin Scorsese cast Milioti as the first wife of Leonardo DiCaprio’s character, notorious New York City stockbroker Jordan Belfort.

Experiencing “The Sopranos” set as vast… Closing down New York City streets on my initial day there was overwhelming! The paparazzi were swarming around the camera, even next to Camera A. It was incredibly intense for the first 10-15 minutes, but it just turned into background noise after that. Yet, it happened consistently. But it’s peculiar… it never really stopped.

The movie had plenty of spontaneous scenes. It offered numerous paths to explore, and initially, I found it challenging to adapt. In hindsight, I wish I’d let go sooner because once I eased up, the entire process became incredibly personal. Martin Scorsese adores actors, and he’s a warm, encouraging, and jovial figure on set, despite his films often being quite intense.

Improvisation was abundant in that film, providing countless options to delve into. At first, I struggled to adjust, but later, when I loosened up, the experience became deeply personal. Martin Scorsese appreciates actors, and he’s a friendly, supportive, and cheerful figure on set, even though his films can be quite intense.

How I Met Your Mother (2013-2014)

Even with a Tony nod and a Scorsese picture, Milioti’s biggest break in 2013 was getting cast as the titular, long-awaited Mother for the CBS sitcom’s ninth and final season. Her performance was so enchanting that fans are still upset about decision to kill her character off in the series finale.

Absolutely, the audience didn’t take kindly to it, and I can see why – it shows they care deeply about the story and characters. It was heartening, really, as I didn’t have a significant role in this particular production. The adoration for that character is indeed a massive compliment, but it also speaks volumes about the groundwork laid beforehand.

Finales are tricky beasts, no doubt. I can empathize with those who were upset, yet I respect them for staying true to their initial vision. It takes courage and conviction to stick to one’s guns in the face of potential backlash.

Fargo (2015)

For Season 2 of the hit anthology series, set in 1979, Milioti played the cancer-striken wife of a Minnesota state patrol officer.

I adored the initial season immensely, and felt it was time for a shift in genres. Following two consecutive network projects where I felt like I was portraying an idealized female character, I decided to steer towards new creative avenues. Acting offers me this unique opportunity; in “The Resort,” I shared a scene with Nick Offerman that we filmed years apart, on a show called “The Resort.” Despite the vast differences between our roles, we were both given a poignant scene about loss. Sitting with Nick in a kitchen in Calgary and later in a jungle in Puerto Rico, we played characters who were vastly different, but who came together to discuss something deeply challenging.

Black Mirror: USS Callister (2017) and USS Callister: Into Infinity (2025)

Milioti plays Nanette, a video game programmer who gets sucked inside her boss’ digital recreation of the 1960s sci-fi TV show “Space Fleet.” Like her character, Milioti was only glancingly familiar with the inspiration for the episode, “Star Trek.”

Experiencing the thrill of darting about with a space pistol in a spaceship made me feel like a 7-year-old again. I got the best of both worlds – the mundane routine of office life and an exhilarating space film adventure! Filming took place on the Canary Islands, where for a week, our entire cast and crew had an entire hotel to ourselves. It was like being at summer camp! We all cruised around on bikes, we all sang karaoke, it was just magical.

For the 2025 sequel, Nanette — now captain of the Callister — gets into several physical fights, giving Milioti her first real taste of stunt work.

I hold tremendous admiration for individuals who persevere through tasks for extended periods. By the end, their bodies may bear marks of bruises, but it’s akin to the exhilaration felt by children while playing in their backyard. It’s that satisfying kind of exhaustion. Additionally, I found enjoyment in subtly portraying characters who might not excel in action, given they spend their days in an office environment. This added layer of character calibration made the whole experience more engaging.

Palm Springs (2020)

In this sci-fi romantic comedy, Milioti and Andy Samberg play wedding guests who fall in love while stuck in a time loop that forces them to repeat the same day.

The script I had, adorned with intricate ‘Beautiful Mind’-like markings, depicted her locations and timelines quite meticulously. Maintaining clarity was challenging, as the script itself mirrored its slippery nature, reflecting the confusion experienced by the characters. On the first day of filming, I found myself repeatedly waking up in the same bed, an event that occurred approximately 20 times.

In the heart of the desert, sudden sandstorms would erupt during filming, forcing everyone to seek shelter immediately. I have a video on my phone capturing Andy and me inside the car, along with the crew wearing goggles, diving under blankets to take cover. The shoot was challenging yet exhilarating, particularly when I got to explore new roles like expressing nihilistic sentiments. I’m drawn to projects that straddle various genres. This one is about characters navigating love, confronting their dissatisfaction, and questioning their role in shaping their lives. And, of course, it also offers the intrigue of time travel!

The Penguin (2024)

Viewers first meet Sofia Falcone after she’s done time in Arkham Asylum, framed by her own father for murders she didn’t commit, and bent on vengeance against the family that abandoned her.

Initially, I was filled with apprehension about whether I’d live up to the expectations for this role, project, or writing. Sometimes, I can become a bit overwhelmed. It feels like imposter syndrome, I suspect. I have such a passion for it that I sometimes get caught up in my own ideas of what I should accomplish. The pressure was immense due to it being Batman and a large-scale production, but over time, it began to diminish. By the end, I had a profound grasp of this character. That’s one of the advantages of long-form storytelling. We filmed “Palm Springs” in just 21 days, so those first eight days were spent worrying quite a bit. On the other hand, “Penguin” took eight months, allowing us to develop our understanding and relationship more deeply because we had more time together.

From the very beginning, she captivated me deeply. Admittedly, I don’t support her behaviors, but the thought of retaliating against those who caused you pain is something inherently human. The experience of enacting this role was exhilarating, and it was rewarding to connect with others who shared similar feelings. Moreover, for a considerable length of time, I had yearned to step into such a character, so I recognized the opportunity as a great blessing.

This interview has been edited and condensed.

2025-06-09 19:18