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

Jonathan Purdon

Jonathan Hirsch

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)