The film that made instant catch-phrases of "You complete me," "You had me at 'hello,'" and "Show me the money!", writer/director Cameron Crowe's superb comedy-drama gave Tom Cruise one of his finest roles as a high-powered sports agent who suffers a crisis of conscience and is promptly fired. Starting out on his own with only a lovestruck assistant (Renee Zellweger in the role that made her a star) and one lone client (Oscar®-winner Cuba Gooding, Jr.), he fights to re-establish himself in a cutthroat business while opening himself up to the assistant and her precocious son (the scene-stealing Jonathan Lipnicki). The splendid cast includes Kelly Preston, Bonnie Hunt, Jay Mohr, Regina King, Jerry O'Connell, Beau Bridges, Eric Stoltz and numerous sports celebrities as themselves (including the "real" Maguire, Leigh Steinberg). If you look closely, you'll spot future stars Lucy Liu, Donal Logue and THE WEST WING's Emily Procter in bit parts...but the most unique "actor" in the cast is long-time Sony Pictures counsel Jared Jussim, who plays the epigram-spouting "father figure," Dicky Fox.