Annie

Cameron Diaz

Linda

Nancy Lenehan

Jay

Jason Segel

Nell

Giselle Eisenberg

Robby

Rob Corddry

Howard

Harrison Holzer

Tess

Ellie Kemper

Clive

Sebastian Hedges Thomas

Walt

Timothy Brennen

Hank

Rob Lowe

Catalina

Jolene Blalock

Max

Nat Faxon

Marta

Krisztina Koltai

Edward

Randall Park

Rosie

Melissa Paulo

Piper Bros. Executive

Joe Stapleton

Graduation Guest

Whitney Meyer

Charlie Newhouse (Radio DJ)

James Wilcox

Beth

Erin Brehm

Punit

Kumail Nanjiani

Kia

Artemis Pebdani

Piper Bros. Executive

Joseph Stapleton

Bodyguard

Melvin Brown

Principal Rodriguez

Osmani Rodriguez

Helper

Samil Battenfeld

Mailman

David "Gruber" Allen

YouPorn Owner

Jack Black

Doctor

Celeste Oliva

Mailman

Dave Allen

Graduation Audience

Christian Alvarado

Parent (uncredited)

Alexis Rosasco

Graduation Grandparent (uncredited)

Michael Maggiani

Graduation Parent (uncredited)

Tiffany Crosby

Parent (uncredited)

Susan Garfield

Parent

Susan Garibotto

Student (uncredited)

Brendan Egan

Student (uncredited)

Kimberly Mae Waller