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'Booksmart' Bonanza and the Best High School Movies, With Olivia Wilde, Beanie Feldstein, and More

May 21, 2019/ 66 min/ Sean Fennessey · Amanda Dobbins

Sean and Amanda praise Olivia Wilde's 'Booksmart,' then each rank their five favorite high school movies. Plus: Sean's South by Southwest interview with the women who made 'Booksmart.'

14 films across 4 segments.

AI-generated This episode was transcribed and analyzed with AI models. The matches aren't perfect — expect the occasional misheard title or a link to the wrong film.

'Booksmart'Olivia Wilde's directorial debut

Booksmart poster

Booksmart 2019

Two straight-A best friends (Beanie Feldstein and Kaitlyn Dever) realize on the last day of school that the slackers also got into Harvard, and set out to cram four years of partying into one night. Sean and Amanda saw it at South by Southwest and loved it: a Superbad-shaped premise that's its own thing, with the leads never the losers of their own story. Billie Lourd steals scenes as free spirit Gigi; script punched up by Katie Silberman; a hip-hop-heavy soundtrack. Opening against Aladdin on Memorial Day weekend for a wobbly Annapurna.

Amanda's Top 5 High School Moviescounted down 5 to 1

Clueless poster
No. 1

Clueless 1995

No. 1 - an authentically funny, sophisticated comedy that both mocks Cher and clearly loves her; Amanda saw it too young and had to be taken by her mother.

Lady Bird poster
No. 2

Lady Bird 2017

No. 2 - the one emotional pick, not straight satire; Greta Gerwig nails mother-daughter friction and an honest, sweet view of female friendship.

Mean Girls poster
No. 3

Mean Girls 2004

No. 3 - Tina Fey making the Heathers idea palatable and mainstream, arriving just as the internet turned it into one of the first meme movies.

Heathers poster
No. 4

Heathers 1988

No. 4 - the 1988 original that laid bare the politics of female friend groups; too dark and spiky to be made today.

Bring It On poster
No. 5

Bring It On 2000

No. 5 - of-the-moment cheerleading satire from the TRL era; Kirsten Dunst as an all-time terrible teenager, and an early stab at class and cultural-appropriation dynamics.

Sean's Top 5 High School Moviescounted down 5 to 1

Superbad poster
No. 1

Superbad 2007

No. 1 - the most accurate screen portrait of not knowing how to do anything; the Cera-Hill dynamic feels lived-in because Rogen and Goldberg started writing it at 16.

Rushmore poster
No. 2

Rushmore 1998

No. 2 - against his own better judgment; the Wes Anderson movie he saw at the right age, a sensory confusion of 'you can do this' that logged itself in his head.

Scream poster
No. 3

Scream 1996

No. 3 - radical for a teen who loved horror, comedy, and meta all at once; every layer works without coming at the expense of another.

Dazed and Confused poster
No. 4

Dazed and Confused 1993

No. 4 - Linklater's gift for casting and one contained night; Randall 'Pink' Floyd as the uniting device that lets the movie bounce figure to figure.

Carrie poster
No. 5

Carrie 1976

No. 5 - De Palma's supersized, near-silent-movie evocation of a bad day in high school; a genuine high school movie under the horror.

The women who made 'Booksmart'recorded at South by Southwest

Booksmart poster
Olivia Wilde, Beanie Feldstein, Kaitlyn Dever, Billie Lourd & Katie Silberman on

Booksmart 2019

Silberman (one of four credited writers) and Wilde wanted smart girls who feel like real people, not a type. Feldstein and Dever lived together through production to build the friendship on screen; a no-sides, everyone-off-book set; Lourd improvised her 4 a.m. scenes.

Fast Times at Ridgemont High poster
Olivia Wilde, Beanie Feldstein, Kaitlyn Dever, Billie Lourd & Katie Silberman on

Fast Times at Ridgemont High 1982

The cast watched it together as a touchstone, for the way every ensemble member is fully formed even in a single scene.

The Breakfast Club poster
Olivia Wilde, Beanie Feldstein, Kaitlyn Dever, Billie Lourd & Katie Silberman on

The Breakfast Club 1985

One of the movies Wilde says she grew up on, and her shorthand for how a high school ensemble lives or dies on chemistry.

Also mentioned raised along the way

Katie Silberman also wrote Isn't It RomanticSet It Up

The 2019 box office around it AladdinLong ShotAvengers: EndgamePokémon Detective PikachuJohn Wick: Chapter 3 - ParabellumGodzilla: King of the Monsters

Runners-up and near-misses American GraffitiThe Last Picture ShowBrickElection10 Things I Hate About You21 Jump StreetSpider-Man: Into the Spider-VersePretty in PinkSay Anything

In passing 22 Jump StreetThe Big LebowskiMarie AntoinetteThe Virgin SuicidesCrazy/BeautifulInterview with the VampireHigh SchoolTapsProject XMean Streets

Not films filtered out: TV, games, ads

TV JustifiedGame of ThronesHeathers (TV reboot)Gilligan's IslandTRL

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