Reuben Feffer is a guy who's spent his entire life playing it safe. Polly Prince is irresistible as a free-spirit who lives for the thrill of the moment. When these two comically mismatched souls collide, Reuben's world is turned upside down, as he makes an uproarious attempt to change his life from middle-of-the-road to totally-out-there.

Genres

Cast

Ben Stiller

Reuben Feffer

Jennifer Aniston

Polly Prince

Philip Seymour Hoffman

Sandy Lyle

Debra Messing

Lisa Kramer

Alec Baldwin

Stan Indursky

Hank Azaria

Claude

Bryan Brown

Leland Van Lew

Jsu Garcia

Javier

Michele Lee

Vivian Feffer

Bob Dishy

Irving Feffer

Missi Pyle

Roxanne

Judah Friedlander

Dustin