Brendan Fraser as Leo Searly

Alex Wolff as Eli Pettifog

Julia Garner as Shauna

Parker Posey as Sheila Pettifog

Michael Oberholtzer as Laird

Greta Lee as Gertrude

Teddy Bergman as Alan

Elisabeth Hower as Eve

Josefina Scaglione as Camilla

Austin Pendleton as Dapper Man

Toby Huss as Whittman Moderator / Brad the Announcer

Robin de Jesús as Romeo Torres

Curtis Gillen as Harvard One

A.J. Shively as Harvard Two

Kevin-Alan Daniels as Harvard Three

Nilaja Sun as Skidmore Moderator

Ash Christian as Cole

Lizzy DeClement as Sophie Searly

Fred Melamed as Benny Greenberg

Colman Domingo as Finals Moderator