Kate Hudson as Andie Anderson

Matthew McConaughey as Benjamin Barry

Kathryn Hahn as Michelle Rubin

Annie Parisse as Jeannie Ashcroft

Adam Goldberg as Tony

Thomas Lennon as Thayer

Michael Michele as Judy Spears

Shalom Harlow as Judy Green

Robert Klein as Phillip Warren

Bebe Neuwirth as Lana Jong

Samantha Quan as Lori

Justin Peroff as Mike

Celia Weston as Glenda

James Murtaugh as Jack

Rebecca Harris as Dora

Archie MacGregor as Uncle Arnold

John DiResta as Joey Sr.

Scott Benes as Joey Jr.

Zachary Benes as Joey Jr.

William Hill as DeLauer Security

Georgia Craig as Receptionist Candi

Liliane Montevecchi as Mrs. DeLauer

James Mainprize as Mr. DeLauer

Tony Longo as Sensitive Moviegoer

Warner Wolf as Warner Wolf

Doug Murray as Mark Sawyer

Natalie Brown as Mrs. Sawyer

Andrew Moodie as Poker Pal Ronald

David Macniven as Poker Pal Francis

Ross Gallo as Young Concession Worker

Gina Sorell as Vegetarian Waitress

Ingrid Hart as Mullen's Hostess

Marvin Hamlisch as Marvin Hamlisch