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Despite getting nominated for a Tony when she was 12 years old, making her film debut in the musical-theater-themed Camp, and turning Pitch Perfect’s low-key folk number “Cups” into a Billboard Hot 100 hit, somehow Disney’s Into the Woods marks Anna Kendrick’s first full-blown movie musical. She picked one hell of a starting place — Stephen Sondheim’s legendary fractured fairy tale packs one doozy of a libretto. Under the eye of Chicago director Rob Marshall, Kendrick co-stars as Cinderella, a dreamer who encounters Emily Blunt’s Baker’s Wife, Meryl Streep’s Witch, and, of course, Chris Pine’s Prince Charming as she wanders through the overgrowth. Songs are sung, high notes are hit, and Kendrick never misses a beat. While in New York, Kendrick sat down with Vulture to discuss grappling with Sondheim on film, evolving Cinderella into a 21st-century character, and looking ahead to her musical follow-up: the Off Broadway adaptation The Last Five Years.

There’s a moment in D.A. Pennebaker’s Company documentary where Elaine Stritch struggles to perform “Here’s to the Ladies That Lunch” while Stephen Sondheim becomes increasingly frustrated. The scene came to mind as I watched you perform Into the Woods’s “On the Steps of the Palace” while wearing a corset. More than typical Broadway shows, do Sondheim numbers need to be conquered? Do they test you?
Are you kidding? Fuck yeah. It’s so complicated. (I’m now thinking about Elaine Stritch and getting all misty-eyed.) It’s so intimidating. The music team — very matter-of-factly — when we started rehearsal, was like, “Oh, ‘On the Steps of the Palace’ is the hardest song in the show.” It’s mean. It’s unkind how hard that song is. They were like, “To be honest, no Cinderella has ever sung it note-perfect before, and you’re going to do it.” Our music director, Paul Gemignani, worked with me on High Society when I was 12. He worked with me on A Little Night Music when I was 17. And he does not suffer fools. He does not mince words. When he tells you that he’s happy, you know it’s true because he has told you many times before that he is not. It was so great to have him there. He’s the one who raised the key to find Cinderella’s voice inside of me, because my tendency is to just power through vocals and make it loud, make it big, put it in my chest. He raised the key, and the first time I sang it through, he was like, “There’s Cinderella.”

How did that change the song?
It forced me to live in that upper register. But then Rob was like, “Okay, but are you sure you want to raise the key, because I’m still going to make you belt that top note?” That last note. I was like [whispering], “I can do it. I can do it.” At the table read, we were all sitting, and I had to run across the room and stand to get that note out. But luckily, I was standing in the recording studio. It’s challenging vocally, but what’s so great about it is you get there, and once you have it, once you have every note, you live in it, and you just ride it. [Sondheim] has written your performance for you in melody. He’s mapped out your emotional journey for you in melody. You just have to keep up.

Was Sondheim present for any of the recordings?
He wrote the updated lyrics for “Steps of the Palace.” He was in and out of the booth with me, which I want to say was so exciting and glamorous, but I was just trying not to piss my pants. I was so intimidated.

What were his notes?
He’s very matter-of-fact. It’s like, “Do it again. Do it again. Great, we can move on.” He’s not an emphatic person. 

Had you encountered him in any of your past musical work?
“Ladies Who Lunch” was in Camp. Which he watched — and again, not a very emphatic man — said, “She has great teeth.” And I was like, “You know what? He didn’t say, ‘She has no business singing that song.’” I’ll take it.

As someone who really respects Sondheim’s work, was there any trepidation over signing up for Disney’s version of Into the Woods?
There wasn’t because it was Rob and it was Meryl, and we had that firepower. If it was a studio like Disney doing it with a director who was very easy to control or didn’t have very strong clarity of vision, then maybe there would be that silly worry that “Oh, the studio’s going to whitewash it.” But they were so excited to have this company of people working on it that they were very hands-off. 

The other day you posted a funny image on Twitter of the original Disney Cinderella telling Prince Charming, “Let’s get one thing straight: I can do whatever the fuck I want.” Anyone who calls themself a feminist has debated the merits of the “Disney Princess.” Do you see your role in Into the Woods confronting a lot of what Disney’s done in the past?
What’s interesting is that these tales have been told for centuries and it must be because there is a resonance in them for every generation. What’s interesting about this version, and what’s very modern about this one, is that not only does Cinderella leave her prince, but she leaves with forgiveness and respect and compassion for the prince. It’s not black and white for her. It’s not even black and white for the prince, who lives a pretty black-and-white life. There’s a moment that’s basically, “This isn’t our path.” [Prince Charming says,] “I shall always love the maiden that ran away.” [And Cinderella says,] “And I the faraway Prince.” There is something extremely relevant and modern about the idea of civility in separation.

How would you compare the work you had to do on Into the Woods to performing the on-screen numbers in your next movie, The Last Five Years. The latter plays quite raw.
The music for The Last Five Years is like running a 26-mile marathon, and singing Sondheim is like ballroom-dancing up Everest. Jason [Robert Brown] is a very, very challenging composer. It’s like trying to compare Rembrandt and Pollock. They’re both artists, and they’re both making you feel, but they do it in unbelievably different ways. Jason also takes you on a journey and finds what is universal in specificity in this amazing way. But, my God, are they doing it in completely different ways.

Were you singing that entire score on set?
The Last Five Years we sang almost everything live. When we’re in a convertible on the West Side Highway, there was no point — it’s not going to be usable sound. But any time we were indoors, we were singing live.

I have to shout-out to a little movie you made with Joe Swanberg that’s now on Netflix called Happy Christmas. It’s pretty much the antithesis of Into the Woods, off the cuff and casually natural. But maybe it presents the same kind of challenge as conquering Sondheim?
Thank you so much. I can’t tell you what that means. That was such an amazing opportunity for me because I worked with Joe on Drinking Buddies. The fact that he saw the capacity in me to play someone broken, I felt so grateful for. I often play people who are very together and maybe a little damaged underneath or a little vulnerable underneath — but to play somebody who’s just falling apart, I was so grateful for that opportunity. It was terrifying. I’m so glad that people responded to it.

Many of Joe’s collaborators have gone on to make their own indie dramas. Would you pick up a camera and shoot your own one day?
Only if we made it for $80,000 at somebody’s house, because that’s how Happy Christmas got made. That’s my comfort zone.

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