Nat Wolff

Nat

Alex Wolff

Alex

Cooper Pillot

Cooper

Thomas Batuello

Thomas

David Levi

David

Joshua Kaye

Josh

Maia Pillot

Teenage Girl Fan

Dominique Patterson

Teenage Girl Fan

Nile Emir Adams

Intellectual Little Boy Fan

Siam Siou

Coffee Shop Guy

Justin Campbell

Street Person

Barbara Eda-Young

Musicologist

Zosia Nahoum

Jump-roper

Veronica Afflerbach

Jump-roper

Jo Jo Scott

Young Rapper

George Stoian

George

Tim Draper

Principal Joe Schmoke

Deborah Offner

Asst. to Principal Schmoke

Judy Anderson

Kindergarten Teacher

John Behlig

Kindergarten Teacher

Cole Hawkins

Cole

Michael Wolff

Nat & Alex's Dad

Jesse Draper

Jesse (Babysitter / Tutor)

John B. Williams

John B.

Ray Chambers

Scratch DJ

James Badge Dale

Romantic Newlywed

Gretchen Egolf

Romantic Newlywed

Mike Hvizdo

Romantic Gay Newlywed

Brad O'Connor

Romantic Gay Newlywed

Allie DiMeco

Rosalina

Shelby Young

Screaming Teenage Girl Fan

Erik Jensen

Photographer

Noelle Beck

Josh's Mom

Phoebe Legere

David's Mom

Jonathan Pillot

Mort Needleman

Samantha Cordero

Autograph Girl Fan

Nastassja Schmiedt

Autograph Girl Fan

Eleanor Draper

Autograph Girl Fan

Johnnie Mae Allen

Teacher Who Gets Flipped

Daniel Tai

Rosalina's Dad

John Rue

Thomas' Dad

Adam Draper

Timmerman Brother

Coulter Mulligan

Timmerman Brother

Billy Draper

Timmerman Brother

Tony Ray Rossi

Upset Father

Mike Rock

Medic

Max Fishelson

Alphabet Burp Boy

Lisa Mulligan

Ears Inside of Head Girl

Eunice Cho

Hoola Hoop Girl

Mikey Kellman

Massage Kid

Tyrel Jackson Williams

Toy Guitar Player

Vic D. Vine

Hardcore Wrestler

David Palumbo

Hardcore Wrestler

Cindy Blackman

Cindy Blackman

Timothy Busfield

Timothy Busfield

Ann Curry

Ann Curry

Polly Draper

Polly Draper

Arsenio Hall

Arsenio Hall

Mel Harris

Mel Harris

Peter Horton

Peter Horton

Ricki Lake

Ricki Lake

Cyndi Lauper

Cyndi Lauper

Melanie Mayron

Melanie Mayron

Julianne Moore

Julianne Moore

Ken Olin

Ken Olin

Brent Popolizio

Brent Popolizio

Tony Shalhoub

Tony Shalhoub

David Thornton

David Thornton

Uma Thurman

Uma Thurman

Patricia Wettig

Patricia Wettig

Nancy Wilson

Nancy Wilson

Maya N. Blake

Madison (uncredited)