John Beckwith

Owen Wilson

Jeremy Klein

Vince Vaughn

Treasury Secretary William Cleary

Christopher Walken

Claire Cleary

Rachel McAdams

Gloria Cleary

Isla Fisher

Kathleen Cleary

Jane Seymour

Zack "Sack" Lodge

Bradley Cooper

Grandma Mary Cleary

Ellen Albertini Dow

Todd Cleary

Keir O'Donnell

Father O'Neil

Henry Gibson

Mr. Kroeger

Dwight Yoakam

Randolph

Ron Canada

Trap

David Conrad

Christina Cleary

Jennifer Alden

Chaz's Girlfriend

Summer Altice

Christina Cleary

Jenny Alden

Betty Cleary

Betsy Ames

Mrs. Kroeger

Rebecca De Mornay

Craig

Geoff Stults

Jennifer

Camille Anderson

Larry Joe Campbell

Vivian

Diora Baird

Italian Wedding Swing Dancer

Jed Bernard

Ivana

Ivana Bozilovic

Attorney

James McDonnell

Chazz Reinhold

Will Ferrell

Chazz's Mom

Kathryn Joosten

Attorney

Jesse Henecke

Hindu Woman

Naureen Zaim

Old Jewish Man

Lou Cutell

Old Irish Woman

Norma Michaels

Brunette

Rachel Sterling

Old Jewish Woman

Sparkle

Old Italian Man

Frank Ray Perilli

Old Italian Woman

Patricia Place

Old Chinese Man

Chao Li Chi

Woman at Jewish Reception

Tanaya Nicole

Old Indian Man

Noel De Souza

Frank Meyers

Ned Schmidtke

Himself

John McCain

Director

David Dobkin