Exclusive: Emily Osment on going from Hannah Montana to Netflix’s Pretty Smart

Production still of Emily Osment in Pretty Smart
Emily Osment is continuing her sitcom legacy. Pic credit: Netflix

Emily Osment has made her name known in the sitcom world, first starring in the hit Disney series Hannah Montana during her pre-teen years. She then went on to play roles in the shows Life With Boys, Two and a Half Men and Mom.

She also starred as the lead in the ABC sitcom Young & Hungry which continued for four seasons. That’s to say, Osment has familiarized herself with the sitcom genre.

Currently, she is starring in a new sitcom, scheduled to hit Netflix on Friday, October 8.

The series, called Pretty Smart, refuses to hold back on all of the fan-favorite sitcom features; it has a strong laugh track, a talented cast with impressive comedic timing, and the most awkward personal crises. Osment plays Chelsea, a recent college graduate who finds herself stuck living with her sister in Los Angeles and her three roommates; influencer Jayden (Michael Hsu Rosen), gym buff Grant (Gregg Sulkin), and spiritual guru Solana (Cinthya Carmona).

Pretty Smart is a multi-camera series, much like Hannah Montana and Young & Hungry. Speaking about her experience going from those roles to this one, Osment told us, “The format was one that I was familiar with but the character was something that was new to me.”

She continued to say, “Unfortunately, it’s rare as a blonde woman in Hollywood to be offered a role where you’re playing someone who’s highly educated, a Harvard graduate. That was flattering to me.”

“But I read it [the script], I immediately connected to that fish-out-of-water feeling that she [her character] had. I remembered when I went to college, I felt really out of place. I connected with that feeling when Chelsea moved back to L.A. being like, ‘I don’t know how to connect to these people,” and there’s a good lesson throughout this first season of just giving people another shot,” Osment shared.

Monsters and Critics had the opportunity to speak with Pretty Smart’s Emily Osment and Olivia Macklin about the premiere of their new show.

Olivia Macklin on making her debut as a Netflix lead

Before starring in Pretty Smart, Olivia Macklin was featured in Dead To Me and FOX’s Filthy Rich. She plays Claire in this brand-new kooky Netflix series.

Claire is a kind-hearted character who, despite her ditzy personality, offers her support and optimistic perspective to help her friends and sister. Macklin and Osment have undeniable chemistry throughout the season, playing distant sisters who struggle to rebuild their relationship. Gushing about Macklin’s performance, Osment told us, “The world is not ready for Olivia in Pretty Smart.”

Talking about her reaction when she found that she got her first Netflix lead role, Macklin said, “As an actor, you dream about what you want, what your dream roles are. And I had a very random list of dream things, it was multi-camera but I wanted to do streaming.”

She continued, “I wanted to play a character that was equally challenging but something that was my sweet spot and I never thought in a million years that I would get to do that.”

“The incredible thing was after auditioning and going through the whole process, when I got it hearing my team say: ‘You really fought for this one, so enjoy this.’ Because I did, I really wanted this part so bad,” Macklin added.

Macklin delivers a flawless performance in Pretty Smart.
Macklin delivers a flawless performance in Pretty Smart. Pic credit: Netflix

Where do you see your character in 10 years?

Popping a fun question to Osment, we asked where she thought her character would be in 10 years. Chelsea, while stubbornly level-headed and ambitious, found herself loosening up throughout the series. She discovered the toxicity in her life; her unsupportive peers, those who used her for her intelligence, and her aversion to mindless fun.

Talking about her character’s future, Osment shared, “I hope she’s still on the West Coast, it seems to be doing her well. I think she should do her best to stray away from any of the routines she had before moving to Los Angeles because it wasn’t doing her justice.”

“She’s the type of person who was going down one path and it worked for her, but she wasn’t being totally fulfilled. And then, she moves in with Claire, her relationship with her sister grows, she gains some friends she didn’t know she needed but she desperately did. And it allows her to unbutton and relax a little bit. The new information and friends you’re able to build when you kinda sit back and say: ‘Okay what do I really need?’ are such important times in her life and hopefully, she sits back with that.”

“I mean wouldn’t it be funny to see her running a surf shop or something, just reading in the background. Serving margaritas or something,” Osment joked.

Watch our full conversation.

Pretty Smart is currently streaming on Netflix.

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