Nat Wolff

Character: Nat

Alex Wolff

Character: Alex

Cooper Pillot

Character: Cooper

Thomas Batuello

Character: Thomas

David Levi

Character: David

Joshua Kaye

Character: Josh

Maia Pillot

Character: Teenage Girl Fan

Dominique Patterson

Character: Teenage Girl Fan

Nile Emir Adams

Character: Intellectual Little Boy Fan

Siam Siou

Character: Coffee Shop Guy

Justin Campbell

Character: Street Person

Barbara Eda-Young

Character: Musicologist

Zosia Nahoum

Character: Jump-roper

Veronica Afflerbach

Character: Jump-roper

Jo Jo Scott

Character: Young Rapper

George Stoian

Character: George

Tim Draper

Character: Principal Joe Schmoke

Deborah Offner

Character: Asst. to Principal Schmoke

Judy Anderson

Character: Kindergarten Teacher

John Behlig

Character: Kindergarten Teacher

Cole Hawkins

Character: Cole

Michael Wolff

Character: Nat & Alex's Dad

Jesse Draper

Character: Jesse (Babysitter / Tutor)

John B. Williams

Character: John B.

Ray Chambers

Character: Scratch DJ

James Badge Dale

Character: Romantic Newlywed

Gretchen Egolf

Character: Romantic Newlywed

Mike Hvizdo

Character: Romantic Gay Newlywed

Brad O'Connor

Character: Romantic Gay Newlywed

Allie DiMeco

Character: Rosalina

Shelby Young

Character: Screaming Teenage Girl Fan

Erik Jensen

Character: Photographer

Noelle Beck

Character: Josh's Mom

Phoebe Legere

Character: David's Mom

Jonathan Pillot

Character: Mort Needleman

Samantha Cordero

Character: Autograph Girl Fan

Nastassja Schmiedt

Character: Autograph Girl Fan

Eleanor Draper

Character: Autograph Girl Fan

Johnnie Mae Allen

Character: Teacher Who Gets Flipped

Daniel Tai

Character: Rosalina's Dad

John Rue

Character: Thomas' Dad

Adam Draper

Character: Timmerman Brother

Coulter Mulligan

Character: Timmerman Brother

Billy Draper

Character: Timmerman Brother

Tony Ray Rossi

Character: Upset Father

Mike Rock

Character: Medic

Max Fishelson

Character: Alphabet Burp Boy

Lisa Mulligan

Character: Ears Inside of Head Girl

Eunice Cho

Character: Hoola Hoop Girl

Mikey Kellman

Character: Massage Kid

Tyrel Jackson Williams

Character: Toy Guitar Player

Vic D. Vine

Character: Hardcore Wrestler

David Palumbo

Character: Hardcore Wrestler

Cindy Blackman

Character: Cindy Blackman

Timothy Busfield

Character: Timothy Busfield

Ann Curry

Character: Ann Curry

Polly Draper

Character: Polly Draper

Arsenio Hall

Character: Arsenio Hall

Mel Harris

Character: Mel Harris

Peter Horton

Character: Peter Horton

Ricki Lake

Character: Ricki Lake

Cyndi Lauper

Character: Cyndi Lauper

Melanie Mayron

Character: Melanie Mayron

Julianne Moore

Character: Julianne Moore

Ken Olin

Character: Ken Olin

Brent Popolizio

Character: Brent Popolizio

Tony Shalhoub

Character: Tony Shalhoub

David Thornton

Character: David Thornton

Uma Thurman

Character: Uma Thurman

Patricia Wettig

Character: Patricia Wettig

Nancy Wilson

Character: Nancy Wilson

Maya N. Blake

Character: Madison (uncredited)