When did it hit you that you were no longer a struggling young woman living in a shit hole in Los Angeles?
Weird things will trigger that sensation of “Holy crap! How did I get here?” It will be like when I’m checking out at the doctor’s office. I vividly remember being 19 years old, not having health insurance and moving to Los Angeles. I needed to go to the doctor, and it was 30 times more expensive than I was expecting it to be. Now when I’m checking out and there’s a balance of $70, I’m like, “Yeah, I’m making it rain up in this doctor’s office!” I very distinctly remember not having $70.
In your new book, Scrappy Little Nobody, you say you knew you were crazy at a young age. Why haven’t you ever seen a therapist?
I never felt normal, but I actually think that’s a way more common feeling than I realized. Honestly, I haven’t been to a therapist because it was one of the many things I thought I would magically know how to do as an adult, but I don’t. I thought someone was going to tell me so many things. Like when I was 25, I wanted to buy a rug. Why didn’t anyone tell me that rugs are like the most expensive thing in the world? People are selling rugs for $10,000 as if that weren’t absolute insanity. Why isn’t that mentioned at some point in your life? “Oh, by the way, people are going to try to sell you rugs that cost so much money that you’re going to want to smash a window.”
You’re now 31. Do you feel younger than you actually are?
I definitely feel like a little old lady at heart. I’m very grumpy and grizzled but simultaneously really immature. So I’m the worst of a child and the worst of an old lady. I’m a treat, basically.
If you can’t get on board with overthinking, I don’t know how much we can connect.
You also say that you’re a “loud, hyperactive loser.” Was it difficult to publish such sharp words about yourself?
I guess the best I can hope for is that people relate to that feeling. If you can’t get on board with overthinking, I don’t know how much we can connect. I’m an overtalker. When I’m trying to figure out what to do about something, I’ll bend someone’s ear. I understand if they just want to duct-tape my face shut.
Your parents divorced when you were 15. Why did you leave that out of the book?
Honestly, it was one of many things I wanted to write about, but it just didn’t end up jelling. It felt more like a police report than a chapter. The miraculous thing about that situation was that my parents were so civil and respectful throughout the process. It made me a poster child for divorce. If they’d stayed together and been unhappy, it would have messed up my understanding of what marriage should look like. I’m very pro-divorce. I know that sounds crazy, but Louis C.K. did this great bit about how divorce should never be sad. There are never two people madly in love and perfect for each other who get divorced.
You’ve said that you feel unworthy of success. Why?
It’s not that I feel unworthy; it’s just that I used to buy into the idea that some people are better. I’m learning every day, over and over, that we’re all the same. Really, it was more that I just wanted to pay the bills doing what I love and, ideally, not have a second job. It was the biggest dream I allowed myself to have.
You’ve sung and acted on Broadway and in movies including the Pitch Perfect franchise and Into the Woods. Which is weirder, watching yourself sing or watching yourself act?
Growing up, people told me I should sing in a recital or something, but it was mostly a way to combat the fact that I wouldn’t fucking stop singing. I really liked to scream-sing. If I’d kept on singing like that, I would have lost my voice before I hit the age of seven. I think it’s less weird to watch myself sing than watch myself act. When I watch myself sing, I can appreciate the music because I didn’t write it. I’ve never written a script either, but there’s something a little rawer with acting. I tried to watch one of my movies alone in a screening room, and the entire time I was thinking, You are a monster. You are terrible!
It seems every time you smoke weed, you get really paranoid. Why the hell do you do it?
[Laughs] About two years ago I had one of those game-changing paranoid experiences, and I haven’t smoked weed since. I was probably remembering all the bad trips. It was a big pastime. For whatever reason, I had more bad experiences than good experiences, so I thought I shouldn’t do it anymore. I’ve never been addicted to anything. I would be a much more interesting person if I were addicted to OxyContin.
You mention in your book that you kept a journal. What did you write about losing your virginity?
I just wrote, “When am I going to lose my virginity? Like, really, when is it going to happen? What is it going to be like? How long, and at what point will it be too late and I’ll have to be a virgin forever because you can’t lose your virginity past a certain age?” I remember literally writing, “It’s going to happen at some point and someone is going to be on top of me, and we’ll be having sex and I’ll probably think of this diary entry.” It’s a pretty meta diary.
We’ve heard that you have a lot of sex dreams. What’s the craziest one?
Oh my God, do I? I don’t want to name the actor, but I dream about someone I find really creepy but other people might find totally attractive. I’ve had two sex dreams about him, which is really awkward. I woke up like, What the hell was that about? I can have a sex dream about anyone in the world and it was that guy? Thanks a lot, dream brain!
Are you pro– or anti–dick pic?
Now, this is a lose-lose question for me. I can’t be pro, because then I’ll get a bunch of dick pics. And I can’t be anti, because I’ll also get a bunch of dick pics. It’s just setting me up for failure. A friend of mine once said she had been to a comedy show, and it changed her perspective on it. This guy said, “If you think you’re hot shit but don’t have a dick in your phone, you need to reconsider it.” I guess that is a way to recontextualize.
What’s the most awkward song you’ve had sex to?
“Lapdance” by N.E.R.D. It was just too on the nose, and we ended up laughing. It’s a really sexy song, but then it was just kind of like…eh. It came on shuffle, and we were both trying to stay in the moment. We were like, “Are we in a music video? What is going on?”
Why are you so uncomfortable doing nude and kissing scenes?
It’s so mechanical; it wasn’t the actor’s idea to kiss me. We just have to look at each other and say, “Okay, I guess we are doing this now.” For women, the fact that someone wants to kiss you is the exciting part. If someone’s kissing you when they don’t particularly want to be, it takes the fun out of it. Also, it’s the makeup department’s job to have mints, which is random. Why the makeup department?
How much did you relate to your extremely type-A character in Up in the Air?
I related to my character a lot, but I think that’s because she’s probably one of the only people on the planet who’s more uptight than I am.
What about acting with George Clooney?
Everything you want George Clooney to be, he is that. I was nervous to act with him, but he was really warm and accommodating. He’s probably used to people being nervous around him at this point.
Your new movie The Accountant came out this October. Ben Affleck’s character is an autistic savant with obsessive-compulsive disorder. How did his condition affect your portrayal of your character?
Ben and Gavin O’Connor, the director, did a lot of research for this film. They really understood the responsibility they had to portray someone who’s on the spectrum. I did my research through reading, and I prepared myself to interact with Ben however he decided to play that character. What was nice for me was playing someone who’s probably the only person in that character’s life who’s in awe of him. She’s not freaked out; she thinks he’s amazing. Since Ben’s character is more closed off, it forced me to listen a lot, which is the best thing you can do as an actor anyway.
You’ve said that singing at the Oscars last year is one of your top three scariest experiences. What was another?
One was when I did Letterman, because I had never done a talk show before. What if I sit down and start screaming? What if the universe swallows me up? He’s terrifying. He wanted me to do “Cups” from Pitch Perfect, and I was like, “Well, yeah, whatever he wants, because he is so biting and his wit is so icy and if you get on his bad side.…” Afterward, I just got the hell out of there, ran to my hotel room and waited for it to come on. I was also on Twitter while watching it, which I would never do now. That’s just setting yourself up for disaster.
Let’s take it a few steps further: Why do you fear death so much?
It’s like from that song: “I swear there ain’t no heaven, but I pray there ain’t no hell.” I was raised going to church, and I had horrible anxiety about going to hell. My parents were like, “Of course you are not going to hell. You are a little girl. What are you thinking?” Were they not paying attention in church when they said that basically anyone who ever does anything bad is going to burn in a fire forever? I wasn’t even Catholic; I was raised Protestant. I think the previous generation got so messed up by Catholic guilt that they went Episcopalian. They thought, Oh, my kids are going to love church. But they’re still reading from the Old Testament. So yeah, I think I’m afraid of being tortured forever. What if hell is real? I’m going to do some good deeds just in case.
How close is the real Anna to the one we see in the media?
[Laughs] I don’t know. Oh my God, I’m going to pee so much after this interview. I was just thinking that if I died and somebody talked to every single friend and acquaintance of mine, and read every journal and diary entry I’d ever written, I don’t think they would know anything about me. I mean, it’s not like my goal is for everyone in the world to know completely who I am.
What was it like having cake smeared all over your face in the upcoming Table 19? Would you ever bring a cake fight into the bedroom?
I loved the cake all over my face. I tweeted at the time that I was covered in frosting and Lisa Kudrow had to brush my frosted hair away from my face. I was living some weird 1990s fantasy. But yeah, I think food in the bedroom could totally go hand in hand, specifically with vanilla frosting. Chocolate I don’t understand. It’s too scatological; it looks like poop. But vanilla frosting I can get on board with. I was trying to be a lady in talking about poop, but I’m not a lady.
To see outtakes from Anna Kendrick’s 20Q shoot, click here.