Cristin Milioti and Andy Samberg on The Penguin, Prosthetic Envy, and the Perfect Karaoke Song

Cristin Milioti isn’t the obvious choice to play an unpredictably murderous aspiring crime lord in HBO’s The Penguin, but that’s exactly what makes her performance throughout the show’s eight-week run so enjoyable to watch. The 39-year-old actor has spent most of her career adjacent to the comedy world, on shows like 30 Rock and How I Met Your Mother, but her turn as Sofia Falcone, daughter of Gotham mob boss Carmine Falcone and foil to Colin Farrell’s Batman archnemesis-to-be—has been at times sympathetic, at times terrifying, but always captivating. Milioti has been doing a lot of press for the show, whose finale airs this Sunday, so to switch things up a bit we asked her Palm Springs co-star Andy Samberg to take a short pause from his stint on SNL to ask his friend some questions about The Penguin. He did his best.

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ANDY SAMBERG: Hang on, recording in progress.

CRISTIN MILIOTI: Wow. Okay. Also, thank you for doing this.

SAMBERG: Give me a break.

MILIOTI: I can’t.

SAMBERG: Okay, so first question. Remember Palm Springs?

MILIOTI: I knew it. Of course I remember it, with nothing but fondness. In fact, I’m going to Palm Springs next month.

SAMBERG: Are you?

MILIOTI: Yeah. 

SAMBERG: Follow-up question. Can I come?

MILIOTI: I would love it if you came.

SAMBERG: I’m not going to ask you who with, because that would be crossing a boundary.

MILIOTI: I’m willing to share, I’m going for a friend’s birthday. A girl’s trip. So excited.

SAMBERG: So I’m for sure going to crash.

MILIOTI: [Laughs] Yeah, for sure. But no, I think about it with fondness all the time. And my phone does that thing that I actually hate, when it says, “A couple years ago, today, you were doing this.” And it’s specifically you and I in that car, on that car rig.

SAMBERG: Goofing hard. I would be remiss to skip over talking about The Penguin. I’ve been watching it. I was going to text you, and then I was like, “Well, I’m going to interview her. I might as well tell her how much I love it in person.” It’s so good. You’re so good. 

MILIOTI: Thank you very, very much.

SAMBERG: So when they offered you the role of the Penguin… 

MILIOTI: I said, “I don’t like the cold and I like to fly, so we’re going to have to change some stuff.”

SAMBERG: [Laughs] As your friend, and as an admirer of your work, it’s so fun to watch you just set loose. Because it’s something we talked about a lot. I always cite the moment we realized we were going to be great friends, which was, we got asked, “What’s a role you wish you’d played?” And you were like, “Beetlejuice.” And I was like, “Oh,fuck, yeah.” [Laughs]

MILIOTI: Absolutely. But yeah, I’ve had the time of my life. The opportunity to really let loose was welcomed.

SAMBERG: I’m one behind, but I’m seeing the flip happening. The ark is in motion. I’m going to say something that’s probably controversial.

MILIOTI: Okay.

SAMBERG: There was a moment where I was secretly hoping you were the Hangman, because I was like, “Oh my god, am I about to get to see Mili as a full fucking serial killer?”

MILIOTI: [Laughs] I still have a huge body count. And the body count continues to rise. Were you familiar with the comics? 

SAMBERG: I did not know these specific ones.

MILIOTI: I didn’t either.

SAMBERG: But I’m sure you’ve deep diven, deep dove?

MILIOTI: I did deep doved, but then they told me early on, “This is going to be different.”

SAMBERG: This ain’t your daddy’s Sofia.

MILIOTI: That’s right. Speaking of which, and I know I texted you this when it came out, but hear me out, the Sushi Glory Hole, I’ve watched it a couple times since we spoke.

SAMBERG: I appreciate that so much.

MILIOTI: It’s really a hit.

SAMBERG: I can’t wait to show you more. I do want to ask you, do you think it’s fair that you’ve been on a Run The Jewels song and I haven’t?

MILIOTI: I feel like it’s fair. You have your own rap career that you’ve built, and I got to feature on one song that’s pretty lit.

SAMBERG: This segues into my next question. You have a beautiful singing voice. Do you ever, while you’re singing, feel like a bird floating on the wind, and totally at peace?

MILIOTI: Absolutely. I was just singing last night, in fact, at a friend’s concert. And me and a bunch of my closest girlfriends, we sang “Hammond Song” [by The Roches].

SAMBERG: Oh, I love “Hammond Song.” Do The Roches know how hard they’re popping off in the last five or six  years? I feel like they’ve had a huge explosion.

MILIOTI: Yeah. I, embarrassingly, didn’t know that song until two years ago.

SAMBERG: I discovered it via a friend during Covid, and then we went on a crazy Roches deep dive. When you sang “Hammond Song,” did you think you sounded better or worse than when you and I would duet “Shallow” on the set of Palm Springs?

MILIOTI: I will never reach as good as we sounded. I was just at karaoke and someone was singing “Shallow,” and I took a video for you, and then I was like, “Does he need another video from me of someone screaming, ‘Shallow’?”

SAMBERG: Of course, yes!

MILIOTI: Then I’ll send it. I was the person that chose it, because I was like, “This is going to get the room popping off.” People look up from their phones for “Shallow.”

SAMBERG: What is it about that song that is karaoke gold?

MILIOTI: I think it feels doable to people, and then you just kind of scream it. It’s like the wonderful alchemy of that song. 

SAMBERG: Remind me, was I Jackson Maine or was I the Gaga part?

MILIOTI: We really switched on and off. It depended on the mood of the day.

SAMBERG: So a follow-up question on SNL stuff. Are you coming to the show this Saturday? And if so, are we hanging out? And are you drinking right now? And if so, what are you drinking? And if so, are you going to order that? And if so, am I going to get the same thing? Are we going to both get the drink?

MILIOTI: We’re going to both get the drink. Do you know what I’ve been drinking of late, because I’ve been singing? Two shots of vodka and two shots of lemon juice, shaken up, on the rocks. It’s very tart and refreshing, and it doesn’t wreck you the next day, but it does get you to a good space.

SAMBERG: You are drinking that because you’ve been singing?

MILIOTI: Yeah.

SAMBERG: I’m for sure interested. I do a lot of vodka sodas. That was always my SNL after party drink, frankly.

MILIOTI: But with just soda or with anything in it.

SAMBERG: Lime.

MILIOTI: Oh, see, what I like about the pure lemon juice is it cancels out the vodka. You’re like, “What a tart lemonade.” And then you go to stand up and you’re like, “Uh, oh.” But yes, we will be hanging out. I don’t have to get up early the next day, so I will be imbibing.

SAMBERG: I’ll probably be flying home early the next day, but I’ll do it anyway.

MILIOTI: Perfect. I was actually trying to think about the last time we saw each other IRL.

SAMBERG: Was it Joanna’s [Newsom, Samberg’s wife] show?

MILIOTI: No. That was pre-pandemic, right?

SAMBERG: You’re right.

MILIOTI: I was thinking about that show the other day, because I went and saw Joni Mitchell at the [Hollywood] Bowl.

SAMBERG: Wait, so did Joanna. 

MILIOTI: Well, I cried the whole time. Just wept and wept and wept. And I was reminded of doing the same thing at your wife’s show. Clutching at my heart, tears pouring down my face, like someone had pushed a button.

SAMBERG: It’s brutal.

MILIOTI: And then ineloquently saying to her after, “Your music makes me aware of my life.” Which is one of the most embarrassing things I’ve ever said to someone I admire. It’s not even fully what I meant. I didn’t know what I meant, I was so overwhelmed.

SAMBERG: Yeah. Her music makes you think about and feel your entire life.

MILIOTI: About being alive, and time, and your inner life, and everyone’s hearts and brains and souls, but yeah.

SAMBERG: Yeah, she’s a jerk.

MILIOTI: But no, I think the last time, weirdly, didn’t we do a photo shoot in the pandemic where we were holding a rope?

SAMBERG: Is that the last time we saw each other in person?

MILIOTI: I think so, because we had to be 10 feet apart.

SAMBERG: That makes me so sad.

MILIOTI: It’s so sad.

SAMBERG: Fuck.

MILIOTI: I know.

SAMBERG: By the way, this is bad copy.

MILIOTI: I know.

SAMBERG: But they can cut it. Well, get ready for a big old hug.

MILIOTI: I’m so excited. I also haven’t been to SNL in a second, I’m really stoked.

SAMBERG: It’s been crazy going back, it’s very different, but also the same in a lot of ways.

MILIOTI: The last time I was there was when Brendan Gleeson hosted, like two years ago.

SAMBERG: That was funny. I was there recently when Stevie Nicks was the musical guest, and I met her. 

MILIOTI: I’d be a blubbering mess. 

SAMBERG: We have the same taste. It was brutal. Her knowing who I was and saying hello, I was just like, “Don’t. No, fuck you, don’t say anything.” [Laughs]

MILIOTI: [Laughs] I’d immediately turn into Chris Farley from SNL, being like, “Do you remember when you were in the Beatles?” That’s what I did to Joanna.

SAMBERG: I know I had to stop myself with Stevie Nicks, from being like, “remember ‘Stand Back?’”

MILIOTI: [Laughs]

SAMBERG: Okay, what else? This is for The Penguin, right? 

MILIOTI: Yeah.

SAMBERG: Okay. Here’s a BTS q. What are the mushrooms made out of?

MILIOTI:  Like the ones that we squeeze with the red stuff?

SAMBERG: Yeah. For Bliss.

MILIOTI: They’re mushrooms. The red was like goopy red dye, but it was sticky.

SAMBERG: Got it. I watched the scene where everyone goes hard on Bliss in the club, and I was like, “I want to try Bliss.”

MILIOTI: You’re not the first person in my life to say that to me. The other night, they were like, “I would do bliss in a heartbeat.” I think we all would. 

SAMBERG: What else can I ask you about? Everyone is always, I’m sure, asking you about the prosthetics for Colin [Farrell].

MILIOTI: They do be.

SAMBERG: Do you ever have prosthetic envy? 

MILIOTI: I was literally just thinking this, because he’s in the chair for three hours. That process is brutal. But as I watched, I slowly began to feel I would kill to do that. I’ve only gotten to wear prosthetics one time on 30 Rock, because they show my character pre-plastic surgery. It was the team from SNL, actually, who came down and put me in all this stuff. 

SAMBERG: What else can we talk about? I feel like I should ask you more about the show, but I know you can’t say any spoilers.

MILIOTI: It’s a lot of spoilers.

SAMBERG: I have questions about the wardrobe, but it’s also so shitty to ask an actress about wardrobe.

MILIOTI: But here’s what I’ll say. I love the wardrobe on this show. Our wardrobe designer is a complete genius, and it was very cool to work together to build the look of a villain. Which, because I’m so obsessed with Batman, to get to be in those fittings and get to collab on what this woman looks like, was wildly cool.

SAMBERG: Okay, good. That was basically the question I was going to ask, was, how much input did you have in it? 

MILIOTI: I had a lot of input on the hair and the makeup, which, that mullet is—have you gotten to the mullet yet?

SAMBERG: I’m not quite to the mullet. I’m one behind. But I will say the eye makeup in the scene where she comes in to say goodbye to the family, I was like, “Oh, this is something. We’re shifting gears.”

MILIOTI: We sure are.

SAMBERG: It was fucking awesome.

MILIOTI: And getting to collaborate on that, and be like, “What if it’s this? And what if it’s that?” And the fittings we did for that dress, and knowing that was going to go with a gas mask, what is that going to look like together? 

SAMBERG: I was so happy for you, watching it. I was like, walking around in this outfit with a gas mask on, has to be your heaven.

MILIOTI: [Laughs] It was my absolute heaven.

SAMBERG: So many beautiful touches. I also really love the line the show walks between DC, Batman, and Gotham ,and real life, New York, New Jersey, things we associate with mob stuff that we’ve watched over the years.

MILIOTI: Totally.

SAMBERG: It’s such a cool synthesis of it. Such a hard trick.

MILIOTI: Yeah. Lauren LeFranc, our showrunner, pulls off so many magic tricks in this show. But that’s one of my favorite ones too, is that you sometimes forget that you’re watching Batman until someone enters in a gas mask and a gown, and you’re like, “Oh my god. Right, sorry.”

SAMBERG: Right, right, right. That fucking scene where the kid’s on the roof with his girlfriend, and you hear the explosions, and it spins around and you start seeing them go off, and then the water comes, that haunts me.

MILIOTI: Haunting.

SAMBERG: It’s crushing.

MILIOTI: Yeah.

SAMBERG: Well, anyway, I guess it’s all leading to me being like, “Put in a good word for me. I’d love to be a screaming guy at Arkham.”

MILIOTI: I would love it. What’s your backstory? Let’s workshop it.

SAMBERG: Okay. So he’s for sure a Looney Tune.

MILIOTI: Yeah. He’s a former resident of Toon Town. Took him to Gotham. He escaped the dip and stuff didn’t go well.

SAMBERG: [Laughs] Let the brass know.

MILIOTI: Yeah, I’ll email the brass.

SAMBERG: I also want to say, just as a suggestion, if you guys do more, a funny set prank would be for you to get full Penguin prosthetics put on, and show up on set.

MILIOTI: [Laughs] Yeah, the crew would love it.

SAMBERG: A goofy, good BTS soc vid.

MILIOTI: Yeah, I love a soc vid, just kidding.

SAMBERG: You love soc vids.

MILIOTI: I don’t know about that.

SAMBERG: We all do. It might be worth it though, for the moment when Colin walks on set and sees you in full prosthetics, and you’re like, “Hey, I’m your stand in.” Just food for thought.

MILIOTI: [Laughs] Okay.

SAMBERG: These are suggestions, they’re not mandates. But since we’re still recording, I think you and Colin are both fucking incredible on this show

MILIOTI: Thanks, Andy.

SAMBERG: And it’s nice to see you, my friend.

MILIOTI: It’s so nice to see you. And I’m so excited to see you on Saturday.

SAMBERG: Same. We have to do a follow-up interview to tell everyone what we drank.

MILIOTI: Exactly. We’ll do it from separate hospital beds.

SAMBERG: That’s perfect.