Ben Stiller as Alex Rose

Drew Barrymore as Nancy Kendricks

Eileen Essell as Mrs. Connelly

Harvey Fierstein as Kenneth

Justin Theroux as Coop

James Remar as Chick

Robert Wisdom as Officer Dan

Swoosie Kurtz as Jean

Wallace Shawn as Herman

Maya Rudolph as Tara

Amber Valletta as Celine

Cheryl Bartel as Ginger

Tim Maculan as Terrence

Jackie Sandler as Bartender

Evgeniy Lazarev as Mr. Dzerzhinsky

Kumar Pallana as Indian Restaurant Owner

Philip Perlman as Phil

Gary Riotto as Drug Dealer

Michelle Krusiec as Dr. Kang

Margie Loomis as Old Biddy

Linda Porter as Old Biddy

Edward Edwards as Antique Dealer

Louis Giambalvo as Pharmacist

Tracey Walter as Pharmacy Customer

John Hamburg as Mr. Friedman

Christina Kirk as Mrs. Friedman

Jenette Goldstein as Moderator

Leyna Nguyen as Newscaster

Chuma Gault as Mailroom Guy

Jim Castillo as Weatherman

Michael Fahn as Sneezer on Train

Roberta R. Deen as Caterer

Christopher Doyle as Tavern Bartender

Christine La Fontaine as Don Piper Fan

Joey Banks as Police Officer

Geraldine Hughes as Receptionist

Picasso as Little Dick

Guiles as Little Dick

Bugsy as Little Dick

Maestro as Little Dick

Will Blomquist as College Student on Subway (uncredited)

Danny DeVito as Narrator (voice) (uncredited)

Azizah Rowen as Barista (uncredited)

Larry Vigus as Man on Street (uncredited)