Kaitlyn Dever

Amy

Beanie Feldstein

Molly

Jessica Williams

Miss Fine

Jason Sudeikis

Principal Brown

Lisa Kudrow

Charmaine

Will Forte

Doug

Victoria Ruesga

Ryan

Mason Gooding

Nick

Skyler Gisondo

Jared

Diana Silvers

Hope

Molly Gordon

Triple A

Billie Lourd

Gigi

Eduardo Franco

Theo

Nico Hiraga

Tanner

Austin Crute

Alan

Noah Galvin

George

Michael Patrick O'Brien

Pat the Pizza Guy

Ben Harris

Yacht Waiter

Kyle Samples

Butler

Deb Hiett

George's Mom

Bluesy Burke

Cindy

Christopher Avila

Rob

Stephanie Styles

Alison

John Hartman

Yacht Waiter #2

Adam Krist

Dick

Gideon Lang

Skip

Ellen Doyle

Murder Mystery Nurse

Maya Rudolph

Motivational Voice (voice)