George Clooney

Michael Clayton

Tom Wilkinson

Arthur Edens

Tilda Swinton

Karen Crowder

Michael O'Keefe

Barry Grissom

Sydney Pollack

Marty Bach

Danielle Skraastad

Bridget Klein (voice)

Wai Chan

Chinese Dealer

Alberto Vazquez

Player #1

Brian Koppelman

Player #2

Tom McCarthy

Waiter (voice)

Denis O'Hare

Mr. Greer

Julie White

Mrs. Greer

Austin Williams

Henry Clayton

Jennifer Van Dyck

Ivy

Frank Wood

Gerald

Richard Hecht

Auctioneer

Bill Raymond

Gabe Zabel

Jonathan Walker

Del (voice)

Sharon Washington

Pam

Cynthia Mace

Wendy (voice)

Michael Countryman

Evan (voice)

Ken Howard

Don Jeffries

Amy Hargreaves

Interviewer

Susan Pellegrino

Secretary

Rachel Black

Maude

Matthew Detmer

Todd

John Douglas Thompson

Jail Guard

Merritt Wever

Anna

Brian Poteat

Deposition Lawyer

Christopher Mann

Lieutenant Elston

Edward Furs

Milwaukee Captain

Katherine Waterston

Third Year

John Gerard Franklin

Correction Officer

Remy Auberjonois

Fifth Year

Pun Bandhu

Fourth Year

Jason Strong

First Year

Robert Prescott

Mr. Verne

Paul Oquist

Starter

Terry Serpico

Mr. Iker

Heidi Armbruster

Anna's Sister

Pamela Gray

Cindy Bach

Andrew Hunter Sherman

U / North (voice)

Kevin Hagan

Raymond Clayton

Julia Gibson

Stephanie Clayton

Sean Cullen

Gene Clayton

Susan Egbert

Michelle

David Lansbury

Timmy Clayton

David Zayas

Detective Dalberto

Douglas McGrath

Jeff Gaffney

Gregory Dann

Cop

Cathy Diane Tomlin

Cop #2

Sam Gilroy

Copy Kid

Maggie Siff

Attorney #1

Sarah Nichols

Barry's Assistant

Susan McBrien

Jean

Jordan Lage

Partner

Neal Huff

First Associate

Paul Juhn

Second Associate

Patrick Askin

Auction Bidder (uncredited)

Angelo Bonsignore

Videographer (uncredited)

Kevin Cannon

Auction Worker (uncredited)

Clem Cheung

Landlord (uncredited)

Tony Gilroy

Taxi Driver (voice) (uncredited)

Emelie Jeffries

Raymond Clayton's Nurse (uncredited)

Josh Mowery

Lawyer (uncredited)

Kimmy Suzuki

Copy Shop Clerk (uncredited)

Steven Weisz

Executive (uncredited)