Jessica Chastain
Molly Bloom

Idris Elba
Charlie Jaffey

Kevin Costner
Larry Bloom

Michael Cera
Player X

Jeremy Strong
Dean Keith

Chris O'Dowd
Douglas Downey

J.C. MacKenzie
Harrison Wellstone

Brian d'Arcy James
Bad Brad

Bill Camp
Harlan Eustice

Graham Greene
Judge Foxman

Justin Kirk
Jay

Angela Gots
B

Natalie Krill
Winston

Madison McKinley
Shelby

Joe Keery
Trust Fund Cole

Michael Kostroff
Louis Butterman

Claire Rankin
Mother

Victor Serfaty
Diego

Whitney Peak
Stella

Jon Bass
Shelly Habib

Joseph Brooks
Eli

Samantha Isler
Molly (age 13-15)

Piper Howell
Molly (age 7)

Kjartan Hewitt
Player

Khalid Karim
Neal

Matthew D. Matteo
Bobby

Jacob Blair
Jeremy Bloom

Chris Boyle
Jordan Bloom

Duane Murray
Agent Delarosa

Jeff Kassel
Donnie Silverman

Dan Lett
David Sagen

Timothy Mooney
Reggie

Leo Vernik
Alex Gershen

John Nelles
Ski Coach

Jason Weinberg
John G

Rachel Skarsten
Leah

Linette Doherty
Court Clerk

Robert B. Kennedy
Alexander Rosenfeld

Morgan David Jones
Brennan

Elisa Moolecherry
Bankruptcy Lawyer

A.C. Peterson
Stranger

Dov Tiefenbach
Club Customer

Bo Martynowska
Club Girl

Amy Rutherford
Doctor

Kris Siddiqi
Guest

David Reale
LA Player

Jake Goldsbie
LA Player

Todd Thomas Dark
LA Player

Chris Owens
LA Player

Gary Brennan
LA Player

George Tchortov
Mike Davidoff

Thomas Hauff
Mr. Sernovitz

Ari Cohen
NY Player

David Lafontaine
NY Player

Jeffrey Parazzo
NY Player

Bruno Verdoni
Pat

Mary Ashton
Tracy

Lizzy DeClement
Skate Rental Woman

Laura Cilevitz
Jeremy's Girlfriend

Amy Stewart
Jordan's Wife

Phil Primmer
Ski Patrol Leader

Gurdeep Ahluwalia
Commentator #1

Dan Duran
Commentator #2

Vladimir Tsyglian
Arthur Azen

Nicholas Banks
Sigel's Lawyer

Michael Cohen
Sigel

Daoud Heidami
Hot Dog Vendor

Maria Lerinman
Waitress

Alyssa Veniece
Bartender

Robin Read
Frederick

Mariah Owen
U.S.A. Ski Team Athlete (uncredited)