Brad Pitt John Smith Angelina Jolie Jane Smith Vince Vaughn Eddie Adam Brody Benjamin Danz Kerry Washington Jasmine Keith David Father Chris Weitz Martin Coleman Rachael Huntley Suzy Coleman Michelle Monaghan Gwen Stephanie March Julie - Associate #1 Jennifer Morrison Jade - Associate #2 Theresa Barrera Janet - Associate #3 Perrey Reeves Jessie - Associate #4 Melanie Tolbert Jamie - Associate #5 Elijah Alexander Marco Racin Ron Bottitta P.J. Miguel Angel Caballero Bellboy - Bogotá Victor A. Chapa Americana Hotel Manager Maree Cheatham Father's Secretary Laine Collins Eddie's Waitress Chris Daniels Mailman Assassin Patrika Darbo 50's Woman Jennifer DeMille Breakfast Diner Waitress Tyce Diorio Salsa Dancer #2 Sabi Dorr Bodyguard #3 Greg Ellis Mickey Megan Gallagher 40's Woman Amy Hathaway Beauty Kathrine Herzer Hopscotch Girl #1 Равиль Исьянов Curtis Stephanie Ittleson Party Guest Mark Ivanir Patron - Dive Bar Benton Jennings Maitre'D Simon Kinberg Investment Banker #1 Peter Lavin Leroy Deren Tadlock Doorman Sean Mahon Lucky Kevin Makely Johnson Edward Padilla Colombian Military Officer Liz Ramos Salsa Dancer #1 Leonard Robinson Watchguard Sam Sabbah Bodyguard Jimmy Shubert Ancient Barker Abigail Rose Solomon Mom #3 Ali Marsh Mom #1 Michael-John Wolfe Bartender - Coleman House Jeff Yagher 40's Man Bryan Anthony Dancer Angela Bassett Mr. Smith's Boss (voice) (uncredited) William Fichtner Dr. Wexler - Marriage Counselor (voice) (uncredited) Tony Longo Big Bad Bathroom Dude (uncredited) Matt McColm Assassin (uncredited) Mo Gallini Algerian Assassin (uncredited)