Owen Wilson

John Beckwith

Vince Vaughn

Jeremy Grey

Christopher Walken

Secretary Cleary

Rachel McAdams

Claire Cleary

Isla Fisher

Gloria Cleary

Jane Seymour

Kathleen Cleary

Ellen Albertini Dow

Grandma Mary Cleary

Keir O'Donnell

Todd Cleary

Bradley Cooper

Sack Lodge

Ron Canada

Randolph

Henry Gibson

Father O'Neil

Dwight Yoakam

Mr. Kroeger

Rebecca De Mornay

Mrs. Kroeger

David Conrad

Trap

Jennifer Alden

Christina Cleary

Geoff Stults

Craig

Jesse Henecke

Attorney

Lou Cutell

Old Jewish Man

Frank Ray Perilli

Old Italian Man

Patricia Place

Old Italian Woman

Chao-Li Chi

Old Chinese Man

Noel De Souza

Old Indian Man

Ivana Bozilovic

Ivana

Camille Anderson

Camille

Rachel Sterling

Brunette

Diora Baird

Vivian

Jennifer Massey

Woman

Larry Joe Campbell

Best Man

Irene Roseen

Elderly Woman

Carson Elrod

Flip

Kathryn Joosten

Chazz's Mom

Tanaya Nicole

Woman at Jewish Reception

Naureen Zaim

Hindu Woman

Melanie Hawkins

Girl Who Cries

Summer Altice

Girl Who Cries

Al Cerullo

Helicopter Pilot

Will Ferrell

Chazz Reinhold (uncredited)

James Carville

James Carville (uncredited)

John McCain

John McCain (uncredited)

Lindsay Schoneweis

Woman in Hat (uncredited)

Kelsey Wedeen

Bridesmaid (uncredited)

Brie Garcia

Wedding Guest (uncredited)