Annie Braddock

Scarlett Johansson

Mrs. X

Laura Linney

Lynette

Alicia Keys

Mr. X

Paul Giamatti

Hayden “Harvard Hottie”

Chris Evans

Judy Braddock

Donna Murphy

Grayer

Nicholas Art

Grayer

Nicolas Reese Art

Milicent

Judith Roberts

Calvin

Nathan Corddry

Jane Gould

Julie White

Tanya

Brande Roderick

Sima

Sakina Jaffrey

Dean

John Henry Cox

Matriarch

Victoria Boothby

Bike Messenger

Lewis Payton, Jr.

Educational Consultant

James Urbaniak

Human Resources Director

Sonnie Brown

Bike Messenger

Lewis Payton

TriBeCa Fashionista

Georgina Chapman

Screeching Lady

Jodi Michelle Pynn

Dude

Mike Rad

Glamour Mom

Joanna Heimbold

Charity Mom

Marla Sucharetza

Xanax Mom

Phoebe Jonas

Eating Disorder Mom

Allison Sarofim

Shopaholic Mom

Tina Benko

Divorcing Mom

Cady Huffman

Bitsy

Kaitlin Hopkins

Doorman

Reathel Bean

Maria

Rosa Nino

Polish Nanny

Matilda Szydagis

Polish Nanny

Matilda Downey*

Loud Nanny

Elle de Amor

Bridget

Alison Wright

Guitar Player

Pete Heitmann

Murnel

Heather Simms

Miss Chicago

Nina Garbiras

Waitress

Melisa McGregor

South American Nanny

Rose Gonzalez

Jamaican Nanny

Shalonne Lee

Whiny Mom

Ilana Levine

Paranoid Mom

Isabel Keating

Carter

Patrick Heusinger

Kenny

Brendan Griffin

John

Aaron Staton

Reggie

Stephen O'Reilly

JoJo

Charlie Hewson

Lizzie

Nicola Barber

Pierrot No. 1

Kevin Kraft

Pierrot No. 2

Nicholas Alexiy Moran

Graduating Student (uncredited)

James Balsamo

Parent at College Graduation (uncredited)

David Boston

Grayer

Nicholas Reese Art

Graduation Crowd Member (uncredited)

Tom Coughlin

Kid (uncredited)

L.J. Foley

Golfer (uncredited)

Roy William Gardner

Lewis (uncredited)

Eli Harris

Nanny (uncredited)

Stella Stark

Flying Nanny (uncredited)

Kimmy Suzuki

Yoga Teacher (uncredited)

Dany Wolf