- The Cast Showoff: You wouldnt cast Kaitlyn Dever, include a karaoke scene in your movie, and NOT have her belt out You Oughta Know, now would you?
- Dawson Casting: Most of the cast of high school seniors are played by actors in their early twenties. Billie Lourd was in her late twenties, and is only 3 years younger than Jessica Williams (Ms. Fine.)
- Irony as She Is Cast: In the film, Amy is a lesbian whereas Molly is straight. In real-life with their actors, it's the other way around: Kaitlyn Dever is straight whereas Beanie Feldstein is gay.
- Method Acting: Before shooting began, Kaitlyn Dever and Beanie Feinstein lived together for a month to help establish a real chemistry between their characters.
- Real-Life Relative: Olivia Wilde cast her husband Jason Sudeikis as the principal.
Trivia / Booksmart