Winter Break

Paul Giamatti

Paul Hunham

Dominic Sessa

Angus Tully

Da'Vine Joy Randolph

Mary Lamb

Carrie Preston

Miss Lydia Crane

Brady Hepner

Teddy Kountze

Ian Dolley

Alex Ollerman

Jim Kaplan

Ye-Joon Park

Michael Provost

Jason Smith

Andrew Garman

Dr. Hardy Woodrup

Naheem Garcia

Danny

Stephen Thorne

Thomas Tully

Gillian Vigman

Judy Clotfelter

Tate Donovan

Stanley Clotfelter

Darby Lee-Stack

Elise

Bill Mootos

Mr. Endicott

Dustin Tucker

Mr. Rosensweig

Juanita Pearl

Mary's Sister Peggy

Alexander Cook

Priest/Bartender

Liz Bishop

Office Lady

Cole Tristan Murphy

Toothbrushing Student

Will Sussbauer

Cobb Salad Student

Carter Shimp

Weed Buyer Harriman

Michael Malvesti

Christmas Tree Guy

Dakota Lustick

Christmas Tree Helper

Melissa McMeekin

Hooker

Jonathan von Mering

ER Doctor

Rena Maliszewski

ER Nurse

Osmani Rodriguez

Pharmacist

Oscar Wahlberg

Pinball Player

Dan Aid

Vietnam Vet Kenneth

Mike Kaz

Hip Party Guest

Kelly AuCoin

Hugh Cavanaugh

Colleen Clinton

Mrs. Cavanaugh

Fred Robbins

Santa Claus

David J. Curtis

Psychiatric Orderly

Pamela Jayne Morgan

Waitress

Davis Robinson

Maître d'hôtel

Joe Howell

Liquor Store Cashier

Peter Krasinski

Choir Leader

Greg Chopoorian

Jason Smith's Father

Ian Lyons

Miss Crane's Boyfriend

Kevin Fennessy

Irritated Movie Patron

Kevin Daigneault

Barton Parent (non-crédité)

Bhanu Gopal

Boston Streeter / Pedestrian (non-crédité)