Characters / Booksmart

Molly

Portrayed by: Beanie Feldstein

• Academic Alpha Bitch: She spent her entire high school tenure focusing on studying, kissing up to the faculty, and scholastic activities like the student government while looking down on everyone who dared to care about things other than academics.
• Big Beautiful Woman: She is a zaftig young woman aware of her "chub" and considered to be good-looking by Tanner and Theo and Jared, the only thing keeping her from being totally desirable is her uptight "butter-personality".
• Break the Haughty: The movie's beginning has Molly discovering that all her studying and avoiding social activities was All for Nothing, as all her classmates she thought were dumber than her who partied in their free time and had active social lives are all going to excellent schools or have lucrative careers ahead of them.
• Control Freak: Molly means well, but she has a tendency to run roughshod over other people (particularly Amy) because she believes her way is the best way and Amy calls her out on this during their big fight.
• Hypocrite: Despite being a self-proclaimed feminist, Molly has no problems repeating the rumours about Annabelle and refers to her by her insulting nickname "Triple A" and tends to view herself and Amy as Not Like Other Girls (at least, not like the ones at their school). Her Character Development sees her grow out of this and she later apologises sincerely to Annabelle.
• Inferiority Superiority Complex: She has an extremely high view of herself but it's clear her ego is also incredibly fragile and built heavily around seeing herself as better than others. Finding out that other people in her class, who didn't take school as seriously as she did, also got into great colleges or have good futures ahead renders her nearly catatonic. And she spends the movie desperately trying to make up for lost time by having as much fun as they did in one night.
• It Amused Me: Despite being straight, she likes pretending that she and Amy are in a sexual relationship because she thinks it's funny to mess with Amy's parents.
• Jerkass Has a Point: During her argument with Amy on Molly's Control Freak behaviour, Amy reveals that, without Molly's knowledge, she had applied for a gap year to travel to Africa. While Molly was clearly in the wrong during the argument and being a huge jerk by picking at Amy's insecurities, Molly did have good reason to be hurt that her best friend had been had been lying to her for months, especially since she planned for them to graduate and move to D.C. together.
• Jerkass Realization: Part of her Character Development is realizing that she was an arrogant, judgmental jerk throughout high school and wasn't really any better than her classmates.
• Jerk with a Heart of Gold: Despite her crassness and abrasiveness, she does warm up to her classmates and truly cares about Amy.
• Ms. Vice Girl: Make no mistake that Molly is a good person and genuinely does mean well, but she tends to be quite uptight and very condescending towards others. The movie has her undergoing some Character Development that ultimately sees her end high school as a kinder, more relaxed person.
• Shipper on Deck:
  • She tries to encourage Amy to speak to Ryan, though with varying results.
  • There's also her excited reactions when Amy and Hope talk to each other at the end of the film.
• Sophisticated as Hell: Despite being usually Sesquipedalian Loquaciousness, Molly has no problem dropping the occasional Atomic F-Bomb.
• Toxic Friend Influence: She's this to Amy on the night of the party, in which Amy gets drugged, humiliated and ultimately arrested, though to be fair, Molly had nothing to do with the last one - Amy decided to distract the cops on her own.
• Uptight Loves Wild: She eventually admits after some prompting from Gigi that she's crushing on Nick, despite herself.
• When You Coming Home, Dad?: Downplayed, as Molly doesn't mention her parents much but when she returns to her apartment, she is greeted by silence and she groans, implying that her parents are working night shifts and not around for her much.

Amy

Portrayed by: Kaitlyn Dever

• Bad Liar: By her own admission, Amy is a terrible liar. She begs Molly to tell her parents that she's staying at her house because she hates lying to them, and when Jared starts weirding her out in the car, she starts making up a ridiculous story about their friend hitting a possum in a bid to leave.
• Cannot Spit It Out: She's pretty much incapable of outright telling Ryan that she likes her, because she's still uncertain about herself and isn't sure if Ryan is gay or not. More seriously, this is also partly what triggers her big fight with Molly, as Amy is unable to explain that the reason she wants to leave the party is she saw Ryan and Nick making out, leading Molly to assume she's freaking out over nothing.
• Earn Your Happy Ending: She saw Ryan while she was making out with Nick, had an argument with her best friend Molly, messed up during her first hookup session and then ended up going to jail. Despite all the things that she went through everything turned out better than expected as she got out from jail, her classmates appreciated her for taking the heat, she reconciled with Molly and eventually she ended up with a hot girl, Hope.
• Extreme Doormat: She complains about it, but Amy tends to go along with what Molly wants even against her better judgement. This eventually makes Amy reach her Rage Breaking Point with Molly when she wants to leave the party but Molly outright refuses to do so, even when Amy has gone through several humiliations because of Molly's obsession with getting to Nick's party. It takes some pretty blunt criticism from Molly and Hope to break her out of this.
• Nice Girl: She's pretty friendly and lacks Molly's haughtiness and oversized ego. See below.
• Not So Above It All: Though she agrees with Molly about feeling under-appreciated at their school, Amy is much less neurotic about her social standing and almost never antagonizes her classmates. While Molly has a complaint lined up for pretty much anyone who crosses her path, Amy is more willing to socialize with people and play along with their quirks. She refuses to call Annabelle by the school’s sexist nickname for her, takes the time to talk with Gigi on Jared’s boat, and shows an interest George’s murder mystery party.
• Shut Up, Hannibal!: When Hope tries to give her a "The Reason You Suck" Speech about her Extreme Doormat nature, Amy hits back that Hope is nothing but a bitchy, popular "hot girl" who tries to pretend she's "telling it like it is", but is really just a mean person and has already hit her peak in high school, something that briefly reduces Hope to a Stunned Silence.
• Straight Gay: A lesbian, although not particularly feminine nor masculine.
• Taking the Heat: Amy decides to use herself as a distraction when the cops show up at Nick's party to give everyone else time to escape.

Jared

Portrayed by: Skyler Gisondo

• Freudian Excuse: Jared outright states that when Molly points out he can't buy people's affection, that his parents do exactly that, implying they are rather neglectful.
• Masculine Girl, Feminine Boy: Feminine Boy to Gigi's Masculine Girl.
• Nice Guy: Jared is extremely wealthy and attempts to buy people's affection because he doesn't know how else to make friends, but he is possibly one of the kindest characters in the film and genuinely means well.
• Spoiled Sweet: Incredibly rich, and still an incredibly nice guy.
• Stepford Smiler: Despite being very friendly, his fellow students are put off by his overbearing nature and besides Gigi, nobody in the school really likes him and Jared knows it.
• Lonely Rich Kid: Even worse as it's likely if he wasn't so rich, he wouldn't have grown up so socially off from his peers.

Gigi

Portrayed by: Billie Lourd

• Ambiguously Bi: She gets very handsy with both Molly and Amy, even tasting the latter’s hair and telling Amy she’s in love with her. The fact that Gigi is constantly drunk and high as a kite make it questionable as to whether these are expressions of genuine attraction or merely drug and alcohol fueled absurdity - Amy even lampshades they've never even had a conversation before now.
• Cloudcuckoolander: Gigi is a very strange person. She makes random comments out of nowhere, can use Offscreen Teleportation, jumps into the ocean, thinks that losing her virginity in a graveyard means she has a haunted uterus and is just generally on her own planet.
• Hard-Drinking Party Girl: Gigi spends most, if not all, of the film drunk or otherwise drug-crazed and knows where every party is
  Gigi: Terry, where's the rubbing alcohol? There's nothing strong enough.
• Masculine Girl, Feminine Boy: Masculine Girl to Jared's Feminine Boy.
• Hidden Depths: Despite coming off as a drunk/drugged up party girl, Jared says she is his only real friend and a very loyal one at that. She's also an exceptional piano player, on good terms with just about everyone in class, got into Harvard largely on merit and is generally a very friendly person.
• Nice Girl: Once you get past her strangeness, Gigi is a very sweet person who cares deeply about those close to her and will do anything for them.
• An Odd Place to Sleep: Gigi is seen sleeping on the hood of a car, as well as on a piano. Both scenes are in the middle of the day, at that.
• Smarter Than You Look: Gigi's...shall we say, eccentric nature does not mean she's stupid. She is very perceptive and socially skilled and she got into Harvard largely on her own merit.
• The Social Expert: Despite Jared saying Gigi is a very lonely person, Molly and Amy specifically go to her to find out where Nick's party is taking place because Gigi knows everyone. She's also shown to be very intuitive, quickly deducing that Molly has a crush on Nick, something her best friend for years didn't even know.
• Spoiled Sweet: Her family is very wealthy but she's a friendly person overall.
• Undying Loyalty: She is extremely loyal and protective of her friends, getting aggressive with anyone she sees as hurting them.

George

Portrayed by: Noah Galvin

• Those Two Guys: Almost never seen apart from Alan.
• Camp Gay: Not quite as much as Alan but he definitely has his moments.
• All Gays Love Theater: Appears to be the student leader of the Drama club, no faculty rep is seen or mentioned.
• Jerk with a Heart of Gold: Is quite arrogant, passive aggressive and snarky, particularly with Molly (appears to have no problem with Amy though), but ultimately never does anything outright cruel to either one and is shown cheering for Molly at the end of the film.
• The Snark Knight: To Molly.
• Attention Whore: Despite taking the directorial role in drama.

Alan

Portrayed by: Austin Crute

• Those Two Guys: Almost never seen apart from George.
• Camp Gay
• Large Ham: And HOW...
  George: (To Alan)You're at a ten, I need you at a two.
• All Gays Love Theater: Implied to be the "star" of the Drama club.
• In Touch with His Feminine Side: Plays a female character at George's murder mystery party and by all appearances relishes the role but is otherwise shown to identify as a male.
• Attention Whore

Hope

Portrayed by: Diana Silvers

• Aloof Dark-Haired Girl: A snarky brunette.
• Defrosting Ice Queen: Becomes nicer as the movie goes on, or at least after the party.
• Jerk with a Heart of Gold: Spends most of the movie teasing or bullying Amy, but hooks up with her in the end.
• Statuesque Stunner: Played by 5'10½ Diana Silvers, who is a full head taller than Amy's actress Kaitlyn Dever (despite Silvers being a year younger than Dever).
• Straight Gay
• Tsundere: Hope is possibly this for Amy. She shows a particular interest in taunting her earlier in the film when she could just as easily have made snide comments to Molly along with Amy or even just Molly. It's possible she just specifically disliked Amy prior to their kiss but given how quickly she was willing to change her mind at the party, this trope could certainly apply
• When She Smiles: Spends the majority of the film up until hooking up with Amy stoic at best and glaring at worst, but when she does smile, it's beautiful and sweet.

"Triple A" Annabelle

Portrayed by: Molly Gordon

• Good Bad Girl: She simply enjoys sex and doesn't try to hide it, even when it results in unwanted nicknames and slut-shaming.
  Annabelle: I'm not, like, gonna suck a dick in my own home where my father can walk in at any moment. Also, I wanna enjoy it— fucking sue me!
• Hidden Depths: Turns out that beyond her partying reputation, she's actually a good student who managed to get a 1560 on the SAT and is Yale bound. As she tells Molly, just because she doesn't only care about school doesn't mean she was slacking off.
• Jerkass Has a Point: She's pretty arrogant and snarky, but Annabelle isn't wrong when she points out that it's not fair that Molly and Amy are blatantly allowed to use their phones in class because they are the Teacher's Pet.
• Jerk with a Heart of Gold: She can be haughty and snarky but she isn't bad. She also reveals to Molly that she was hurt at the rumors and nicknames, especially from other girls, and asks Molly to only address her as Annabelle when they get to Yale.
• One of the Boys: We only see her hanging out with boys at school and she outright admits later she doesn't really have any female friends, something that actually saddens her.
• Only Known by Their Nickname: She's only revealed to be called Annabelle near the end of the movie.
• Slut-Shaming: A victim of this. Annabelle's nickname in school is "Triple A" (American Automotive Assistance) for offering supposed roadside assistance to a number of guys but obviously did more than that. She later reveals to Molly how much she hates that nickname, as she genuinely did help them, although it was sexual too. What hurt her most is she expected the guys to catch on to that nickname, but didn't realize how much the girls would do it too.

Ms Fine

Portrayed by: Jessica Williams

• Cool Teacher: Somewhat Deconstructed, as while Molly and Amy certainly think she's cool and she not only picks them up from the pizza place, but lets them borrow her clothes to wear (which she just so happened to have in her car), it's implied the reason she did this wasn't merely altruism but because she misses the days of being wild and carefree and is desperately seeking to reclaim the freedom of her teenage years. This leads her to end up sleeping with Theo, something she deeply regrets the next day.
• Noodle Incident: She did something that got her banned from Jamba Juice. Every Jamba Juice.

Principal Brown

Portrayed by: Jason Sudeikis

• Putting the "Pal" in Principal: He seems to see himself as this, although by the final day of school he's more keen to see everyone on their way and not have to deal with Amy and Molly's concerns about transitions to the next year's student government:
  Principal Brown: Ladies, it's the last day, you know? We did it, huh? We got you through high school. Can't we just graduate, head off to college, you know, celebrate this wonderful achievement? Let's get through the day without anything horrible happening.
  • It kicks in with a vengeance when he shows up as the girls' Lyft driver:
    Molly: Principal Brown?
    Principal Brown: Principal Brown was my dad. Just call me Jordan.
    Molly: No, thank you.

The Pizza Guy

Portrayed by: Mike O Brien

• Affably Evil: Spends most of the scene where the girls are in his car explaining what a bad idea it is for them to do it, making him seem like a genuinely concerned, good guy. But he's actually a wanted serial killer.
• Creepy Good: Subverted. He gives a nightmarish detail of how Amy and Molly could get murdered, but it's to warn them to not repeat their extremely risky behavior. This would make him this trope, but the whole being a murderer thing does away with the good, making him just creepy.
• Suspiciously Specific Denial: He goes into a lot of detail about how he could potentially kidnap and murder the girls. Turns out he would know, as he's really a serial killer.