8 most endearing side characters from Booksmart

Booksmart is an awesome new teen comedy. What makes it extra special is its fantastic side characters. Here are a few of our favorites.

Olivia Wilde makes her directorial debut this weekend in the critically acclaimed coming-of-age film, Booksmart. It’s a little like Superbad, a little like Mean Girls, but ultimately, Booksmart is an original take on the genre that focuses on its heart, the epic friendship between two young women preparing to graduate high school.

But before they go, they decide to have one epic night where they break all the rules they spent years of their life following.

What makes Booksmart such a spectacular movie is its brilliant ensemble cast. For once, we have a high school movie that doesn’t feel like a make-believe Hollywood fantasy. This is easily one of the more realistic depictions of high school teens and life that I’ve seen on-screen.

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Booksmart should certainly become a teen comedy classic in years to come, if only because all the characters are likable and have depth and they’re not treated less-than or like idiots just because they’re young!

8. Theo

A long-haired lothario who failed 7th grade three times and yet still secured a job at Google, Theo is a little dopey but still cute. I admit I found his relationship with Mrs. Fine a bit strange but the dude is 20 years old.

Plus he never got too weird or pushy with her and despite the strange randomness of the hookup, it kind of made sense. Plus it was nice to see his friendship with Nick not be made into typical douchebag jock guys.

7. Principal Brown

Played by Olivia Wilde’s husband and SNL funnyman, Jason Sudeikis, Principal Brown is the perennial exhausting school-dad character. He loves the students at his school but he is also beyond ready for summer break.

To earn a little extra cash on the side, Mr. Brown drives a Lyft and happens to pick up Amy and Molly on their way to Nick’s party. It’s an intensely awkward drive, one that ends in Amy and Molly streaming porn and getting it blasted over the car’s radios!

6. Jared

Awe, poor, hapless Jared. You can’t help but feel bad for the guy even when he’s at his most cringe-worthy. All he wants is for people to care about him and he doesn’t know how to do that so he throws money at everything in an attempt to buy affection.

Beneath the veneer, he’s actually a sweet guy who loves airplanes and musicals. It’s what ultimately earns him a kiss from Molly.

5. Charmaine & Doug

Will Forte and Lisa Kudrow were cast to play Amy’s parents and perhaps the one major flaw of this film is that they’re only in two scenes!

I pray they’re in some outtakes or deleted footage on the DVD/Blu-Ray release because in their scant seconds they were comedy gold. From fondling Amy’s mastur-bear to naming all her graduation snacks, I wanted more of them together.

4. Hope

She’s the typical hot-bad-girl at school. She’s above it all and edgy and totally has a thing for Amy, hence why Hope is always antagonizing her. This results in a torrid make-out session in the middle of Nick’s party. Unfortunately, it ends with Amy throwing up all over Hope, instantly killing the mood.

Thankfully, Hope isn’t the jerk she pretends to be. She likes Amy, as shown by the fact she shows up at her house the next day to bring her clothes and drop her phone number off. I wish we’d gotten a little more time to see them together but it was super sweet (and the finger faux pas was hilarious, as Molly refuses to let Amy forget).

3. Annabelle (Triple A)

Molly Gordon captured my heart when she played Melissa McCarthy’s daughter in Life of the Party so I was already endeared to her from her first scene, even if she was kind of mean. Molly isn’t a vapid mean girl, she’s actually pretty nice and even picks Molly up after the party so she doesn’t have to walk home.

But my heart broke for her character, Annabelle, when she admits being called “Triple A” gets to her, mainly because girls do it too. She wants people to learn her name at Yale next year and asks Molly nicely, to not bring it up. I hope these two become friends as freshmen.

2. Mrs. Fine

Have you ever had an amazing teacher who you wind up bonding with outside of the classroom? I can’t blame Molly and Amy for being a tad obsessed with Jessica Williams aka Mrs. Fine. She rocks.

Maybe her boundaries are a little strange (she does hang out at a teen rager) but she’s a great addition to the film and fabulous mentor to the main duo. Plus she’s seen Gilmore Girls like 50 times which is like, the biggest mood.

1. Gigi

Easily my favorite character in the whole film apart from Amy and Molly, Billie Lourd literally steals every single scene she’s in. Not only is she hilarious but she adds such a whimsical, chaotic, and exuberant energy to the movie.

Her character, Gigi, is a tad crazy, but supremely loyal, she reads auras and wears magnificent outfits. She’s completely dramatic and yet also the best person to be around. She’s enigmatic and Lourd is a true star. Her character is an instant icon.

What did you think of Booksmart in theaters? Which characters were your favorite? Let us know your thoughts in the comments below!

Booksmart is now playing in theaters.