George Clooney

Michael Clayton

Tom Wilkinson

Arthur Edens

Tilda Swinton

Karen Crowder

Sydney Pollack

Marty Bach

Michael O'Keefe

Barry Grissom

Ken Howard

Don Jeffries

Sean Cullen

Gene Clayton

Merritt Wever

Anna

Austin Williams

Henry Clayton

Robert Prescott

Mr. Verne

Terry Serpico

Mr. Iker

David Lansbury

Timmy Clayton

Bill Raymond

Gabe Zabel

David Zayas

Detective Dalberto

Christopher Mann

Lieutenant Elston

Denis O'Hare

Mr. Greer

Julie White

Mrs. Greer

Frank Wood

Gerald

Heidi Armbruster

Anna's Sister

Sharon Washington

Pam

Danielle Skraastad

Bridget Klein (voice)

Cynthia Mace

Wendy (voice)

Jonathan Walker

Del (voice)

Michael Countryman

Evan (voice)

Douglas McGrath

Jeff Gaffney

Pamela Gray

Cindy Bach

Julia Gibson

Stephanie Clayton

Jennifer Van Dyck

Ivy

Susan McBrien

Jean

Amy Hargreaves

Interviewer

Susan Pellegrino

Secretary

Rachel Black

Maude

Matthew Detmer

Todd

Kevin Hagan

Raymond Clayton

Susan Egbert

Michelle

John Douglas Thompson

Jail Guard

Edward Furs

Milwaukee Captain

Remy Auberjonois

Fifth Year

Katherine Waterston

Third Year

Pun Bandhu

Fourth Year

Jason Strong

First Year

Wai Chan

Chinese Dealer

Alberto Vazquez

Player #1

Brian Koppelman

Player #2

Richard Hecht

Auctioneer

Brian Poteat

Deposition Lawyer

John Gerard Franklin

Correction Officer

Paul Oquist

Starter

Andrew Hunter Sherman

U / North (voice)

Gregory Dann

Cop

Cathy Diane Tomlin

Cop #2

Sam Gilroy

Copy Kid

Maggie Siff

Attorney #1

Sarah Nichols

Barry's Assistant

Jordan Lage

Partner

Neal Huff

First Associate

Paul Juhn

Second Associate

Tom McCarthy

Waiter (voice)

Tony Gilroy

Taxi Driver (voice) (uncredited)

Patrick Askin

Auction Bidder (uncredited)

Angelo Bonsignore

Videographer (uncredited)

Kevin Cannon

Auction Worker (uncredited)

Clem Cheung

Landlord (uncredited)

Emelie Jeffries

Raymond Clayton's Nurse (uncredited)

Josh Mowery

Lawyer (uncredited)

Kimmy Suzuki

Copy Shop Clerk (uncredited)

Steven Weisz

Executive (uncredited)