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

James McDonnell

Attorney

Jesse Henecke

Attorney

Lou Cutell

Old Jewish Man

Sparkle

Old Jewish Woman

Frank Ray Perilli

Old Italian Man

Patricia Place

Old Italian Woman

Chao Li Chi

Old Chinese Man

Norma Michaels

Old Irish Woman

Noel De Souza

Old Indian Man

Ivana Bozilovic

Ivana

Camille Anderson

Camille

Rachel Sterling

Brunette

Diora Baird

Vivian

Ned Schmidtke

Frank Meyers

Jennifer Massey

Woman

Dylan James Turner

Bratty Kid

Sophia Blouin

Flower Girl

Stephen J. Downs

Franklin

Larry Joe Campbell

Best Man

Mark Duane Anderson

Secret Service Agent

Irene Roseen

Elderly Woman

Jules Mandel

Rabbi

Betsy Ames

Betty

Carson Elrod

Flip

Kathryn Joosten

Chazz's Mom

Summer Altice

Girl Who Cries

Lisa Beach

Wedding Planner

Al Cerullo

Helicopter Pilot

Will Ferrell

Chazz Reinhold (uncredited)

James Carville

James Carville (uncredited)

John McCain

John McCain (uncredited)

Brie Garcia

Wedding Guest (uncredited)