Put Chloe Fineman In Everything

Last year, Chloe Fineman hit her 100th episode of Saturday Night Live — and six years into the job, she’s having more fun than ever. “I feel a lot less crazy there, as you learn the ups and downs and how to just genuinely enjoy it,” she says. “Comedy is at its best when you’re being loose and at its worst when you’re really tense and overthinking things. All my best stuff I’ve ever gotten on the show has been Plan D or ‘I don’t know, how about this?’ It’s not the thing I’d spent all night meticulously trying to make work.”

That game-for-anything approach is on full display in Fineman’s two movies this year. In Freakier Friday, she has a brief appearance as a Down Under dance instructor who helps Lindsay Lohan and Manny Jacinto’s characters with some Dirty Dancing-level wedding choreography. “That morning, we learned the whole dance in, I don’t know, 30 minutes,” Fineman, 37, recalls. “It was true fake-it-till-you-make-it.”

She also showed off a very different set of dancing skills as a stripper named Santa Monica in Hulu’s Summer of 69. The film follows an awkward high school girl (Sam Morelos) who seeks Monica out as a mentor when she decides the only way to land the boy of her dreams — and unlock her self-confidence — is to master his favorite sex act.

For Fineman, who grew up in California’s Bay Area, the film was a “love letter” to her high school friends. “What drew me to this move was: You don’t really see a girl explaining this stuff. My educators were these older girls being like, ‘That’s how you give a blow job,’” Fineman says. “It was fun getting back to un-prude Chloe in high school, teaching this kid the ropes in the way that my friends always did.”

On what she was like as a teenager:

I wanted to be an actrivist. I put on The Vagina Monologues at my school when they wouldn’t let me. I was very self-righteous and really into being a feminist. I was much more uninhibited than I am now, which I feel like is saying a lot because I’m a pretty uninhibited person. I feel like I probably flashed too many people as a high schooler.

On sneakily befriending Lindsay Lohan:

I was getting hair extensions to play a stripper in Summer of 69 with my friend Jacob, who does them at a salon called Mèche. Lindsay Lohan was there getting her hair done for Freakier Friday. Because I saw her go over by the sink, Jacob and I had this whole plot where he pretended he had to wash my hair. I turned around [to Lohan] and was like, “Oh my God, hi!” We ended up talking and literally becoming friends at the hair salon that night, which was the coolest thing in the world. She’s the most down-to-earth, real, cool person. And then a month later while I was filming Summer of 69, Lindsay texted me like, “Do you want to be in this movie?”

On her outrageous accent in Freakier Friday:

I hope I don’t offend Australian people. It was definitely a day-of decision, because they added this character — my assistant, Beth — and just saying Beth [in an Australian accent] was funny. I’d also been listening to a podcast around that time called Who Sh*t on the Floor at My Wedding?; there are these two New Zealand women, and it’s a real “poodunnit,” exploring who took a sh*t on the floor at their wedding. My love of that podcast wound up in the movie.

On her favorite SNL 50 memories:

I was going into my dressing room, and Billy Crystal was just at my door. He was like, “I used to live here,” in that very twinkly-eyed Billy Crystal way. Something came over me, and I was like, “Can you sign my wall?” So I have this amazing signature of Billy Crystal that says, “I used to live here.”

We had to share dressing rooms with old castmates, and for whatever reason — I don’t know if it’s my love of interior design and candles and velvet — they were like, “Kristen Wiig is sharing with you.” So I was like, “Kristen, will you sign this?” By my light switch, it says, “Chloe, you’re a…” and then points to the light. And then at the very end of the 50th, Kristen gave me a big hug and was like, “Look behind your door.” She got Bill Murray to sign my wall!

On the rejected ideas she can’t stop pitching:

Ooli, I pitched that character to death. When I finally got a sketch with her on — that weirdly had Elon Musk in it — [segment director] Paul Briganti was like, “I’ve never seen someone pitch something so much.” I still feel like I haven’t cracked her and would love to try her again. Bowen and I have a med-spa talk show we’ve pitched three times. Maybe people find it gross, but I’m in LA right now, and I’m like, “This is the most topical sketch, we need to make it.” “Forever 31,” we first pitched with Lady Gaga, and they did a mascara ad instead.

You have to be really artful at SNL. There’s a little dance of selling the host on it and not letting them know that we’ve tried it before, and giving enough space [between pitches] that people kind of forget you tried it a month ago. But with Ooli, I think I just shoved it down people’s faces until they were like, “OK, fine.”

On the biggest lesson she’s learned from SNL:

It’s this weird show where every Monday, you get to start over. There’s something really Zen about it. It’s like a Buddhist exercise: You do this thing, and then it’s all forgotten. The people who I look up to on the show are always reinventing themselves. I remember the year when Cecily Strong got really into slapstick and was doing all this physical comedy. You don’t have to know it all. But SNL is a special place that really allows you to learn and challenge yourself.

Check out the rest of Bustle’s Entertainers Issue here, featuring interviews with Brittany Broski, Domhnall Gleeson, Jenny Han, Janelle James, KATSEYE, Kesha, Jinkx Monsoon, and Nicole Scherzinger.

This interview has been lightly edited and condensed for clarity.