Emily Osment

How did you get involved with Pretty Smart?
I got a call saying there was a script I should read because I liked the people behind it, and they were right. I loved Chelsea as a high intellectual who takes this unexpected journey with the help of her estranged sister. It’s the coming together of 2 very opposite people [and] a story about friendship and a sister bond. And I loved the opportunity to work with Gregg Sulkin again.

What’s Gregg like?
Oh, lovely. He’s ridiculously sweet and very talented. We were on Disney together, then we did a movie in 2013 that really brought us together. We reconnected again in 2018, and he’s just always been around. We have such a wonderful, long friendship, and having him on this was such a comfort.

Chelsea is a pompous brainiac. Has it been difficult playing her?
Bringing a loving nature to her when she’s being harsh and judgmental was a fine line to walk, but it’s a good lesson for all of us to not immediately judge someone for the way they act or the things they say. I mean, who knows how you’re waking up that day? You have to give people a fair shot, and she learns to do that throughout season 1. We’re very different, but it wasn’t difficult to play her, and I think that’s a testament to our wardrobe department. As soon as I put on that hideous tweed jacket, I was like, “Ohhhhh, yeah.”

Is there something you always look for in a project before signing on?
I always look to play a character I haven’t played before. And obviously, diversity’s very important. The writing staff of this show is so diverse and brilliant. I feel like every character is represented so well. Our writers’ room’s LGBTQ community is writing for Jayden, so everybody’s represented by people similar to them. We don’t have a bunch of straight white men writing a gay love scene. That doesn’t make sense!

You’ve been acting since you were a kid. Has the way you approach a role changed at all?
It has and it hasn’t. I try not to plan ahead too much. You can’t really say, “I’d love to do a show like this,” or, “I’d love to play a character like this.” You just don’t know what’s in store for you, so you have to take it as it comes. This show came at a time when I was looking for work, and I don’t do well when I’m not working. When I saw who was involved, it just seemed like a no-brainer.

Do you have any dream roles?
I’m excited as I get into my 30s to get away from what’s familiar. Sitcom is something I know very well, [but] that’s why I feel like I should stop doing it. Once it feels comfortable, you’re like, “Oh, God. Time to do something else.” I’d love to do something more physical. I grew up an athlete and I never get to do that [in my roles]. I played an assassin one time on a show. I got to do 2 seasons with Emmanuelle Chriqui. It was awesome! We played bad*ss female killers.

So a Hannah Montana sequel is not in the picture?
I don’t think so. [Laughing]. I mean, [the idea] gets tossed around. I’m not sure it would be in the cards for me, but who knows? It’s so funny that my life on that show was paralleled to my life in high school. I was so consumed by SATs and getting into college and who was going to ask me to homecoming—all the normal childhood things we go through. Being on a television show was just not the thing I was focused on. But it was very rewarding and taught me a professionalism I’m appreciative for.

What shows are you binge-watching right now?
I just finished Sex Education. It’s so good. That’s the show of our generation. And of course, Ted Lasso. I get home at the end of the day and I’m like, “I just want to watch something that’s happy, that makes me feel good.” I’m so grateful for all the content we have, especially after a year and a half of it being difficult to work in television. I’ve done 3 projects during COVID and every single production had its own challenges. We were lucky with Pretty Smart because our entire cast was vaccinated. Of course, we were still very careful, but it made it easier to relax.