Sir Michael Caine had decided to quit acting after being greatly disappointed with the production of Bullet to Beijing (1995) and the sequel, Midnight in Saint Petersburg (1996). Jack Nicholson convinced Caine to come out of retirement to work on this movie. Caine had such a good time that he decided to continue acting.
Jennifer Lopez stated in an interview that she shot a nude sex scene with Stephen Dorff for this movie, but that it was cut out of the theatrical release.
(At around one hour and twenty-four minutes) A damaged Volkswagen Beetle from 1970 appears. Jack Nicholson drove the same car in Five Easy Pieces (1970).
Ethan Hawke was the first choice for the role of Jason. He had a long phone conversation with Jack Nicholson trying to convince him, but he was finishing his first novel, The Hottest State, and turned the role down.
Jack Nicholson's and writer and director Bob Rafelson's last movie together, the first was Head (1968).