In one version of the scene where Martin walks into Debi's radio booth for the first time, Minnie Driver decided to let her character put all the cards on the table and just kiss John Cusack. George Armitage said, "It was just wonderful, completely out of the blue. You should have seen the smile on Johnny's face afterwards."
Features appearances by most of the acting members of the Cusack family: John Cusack, Joan Cusack, Ann Cusack and Bill Cusack. Only one sister, Susie Cusack and father Dick Cusack, are absent.
According to George Armitage, he "basically shot three movies simultaneously": one that stuck to the script, one that was "mildly understated", and one that went "completely over-the-top" in terms of improvisation and energy. It was usually the third version that got used. This means there could be alternate takes of nearly every scene still out there somewhere, depending on whether the studio retained the footage and what happened to it in the intervening years. (So far, the film's DVD and Blu-ray releases haven't had any of them.)
Martin's invitation to his high school reunion, which is tucked into the mirror as he gets ready, requires attendees to "Dress to Kill".
The goon stalking Martin Blank is portrayed by Benny "The Jet" Urquidez, a world-champion kickboxer who was also John Cusack's kickboxing instructor.