Shane Black became the first writer to sell a script for four million dollars. He later admitted that this caused a lot of envy among his fellow screenwriters, as well as accusations of commercialism. He voluntarily retired from the blockbuster industry for almost a decade as a result.
One of the movie's original locations was a historic, grand hotel in Muskoka, Ontario, Canada - the 100-year-old Windermere House. During filming, however, the hotel caught fire and burned to the ground. The heat from the film lights were initially blamed for causing the blaze, but it was never proven that the lights started the fire.
"RFK 575" is the license plate used in the film for the dead terrorist's car. It's also the license plate used by Derek Zoolander's roommate in Zoolander (2001) and in a car in Final Destination (2000).
The ice skating scene was scripted to end with Samantha performing a double axel flip and simultaneously firing over her upside-down head. After two aerial-rig configurations (in sub-zero conditions) and several attempts at green-screening failed to hold any convincing fluency to the action, it was dropped from the final cut of the film.
The resort Windemere House in the Muskoka region of Ontario, Canada burned down while filming scenes there. The production company had to rework the scenes in Collingwood, Ontario. Windemere House has since been rebuilt.
The film is famous for being one of the three big-budget films that came out of indie studio New Line Cinema in 1996, and underperformed. The other two pictures were "The Island of Dr. Moreau" and Last Man Standing". Up until their releases, New Line had specialized in low-to-medium-budgeted genre pictures.
Female rapper and Murder Inc. recording artist Tiffany Lane, uses the name "Charli Baltimore" (sic) as her moniker. Lane was a lover of famous New York rapper The Notorious B.I.G who had recorded a song called "Long Kiss Goodnight" for his 1997 album "Life After Death".
According to the CIA personnel file shown during the opening credits, Charlene Baltimore was born in New York City, is six feet tall, and her Social Security number is 079-48-6884. What appears to be a date of birth is mostly obscured, but the year 62 (for 1962) is visible. Geena Davis was born in January 1956.
Shane Black's original script for this film was darker and more graphic than the final film. Amongst the many differences, it included some alternate action sequences, and more violence, like the scene where Mitch and Charly are captured and get tortured. Both characters also had bigger backstories in the original script, Mitch, at one point, tells Charly how he was gang raped in prison, and how his wife refuses to let him see his son, because of what happened to him, and Charly also had more of a dark backstory in the script, than in the film.
When Mitch and Trin pull their scam on the "Man in bed", Mitch and two other actors pretend to be police detectives. Ironically, the room was full of actors who have portrayed cops (at least once) in popular movies and television shows. Rex Linn (man in bed) portrayed a Detective on CSI: Miami (2002), Melina Kanakeredes (Trin) portrayed a detective on CSI:NY (2004), Shawn Doyle (Bum Cop) portrayed a detective in the movie Frequency (2000), and Samuel L. Jackson (Mitch) portrayed a cop in the movie The Negotiator (1998).
Screenwriter Shane Black sold the script for the movie with the intention of Renny Harlin directing it and Geena Davis starring in it. Harlin then told him that he and Davis were contractually bound to make Cutthroat Island (1995) first, which became one of the biggest box office bombs of the decade. Black later stated that this may have caused bad advertisement that worked against this movie as well.
The song "Let It Snow, Let It Snow, Let It Snow" by Dean Martin plays in Samantha's car radio. The same song, sung by Vaughn Monroe, also featured at the end of Die Hard 2 (1990) also directed by Renny Harlin.
Writer trademark: Shane Black: [disarmed gunman]: While being held at gunpoint, Charly disarms the gunman when he is distracted. Black's screenplays often contain scenes where the hero is able to surprise a gunman who makes a fatal mistake, like in The Last Boy Scout (1991) and Kiss Kiss Bang Bang (2005).
In the scene where Charly is supposed to be killed by Jack, you can see in the background a Mercedes Benz W 111 Hardtop Coupé, according to a shortly seen chrome blink on the right side of the trunk lid probably a 280 SEb 3.5 liter V8.
One scene is clearly shot in Toronto,Ontario, not the U.S. This is at the corner of Bathurst and Bloor Streets. The Honest Ed's storefront is clearly visible. Honest Ed's is a well-known store, owned by businessman Ed Mirvish.