Bruce Willis tried to contact Matthew Perry to get him to take part in the film while, unbeknownst to him, Perry was on vacation. After a few weeks of trying to get hold of him, Willis left the famous line, "I will chop off your legs, set fire to your house, and watch you drag..." on Perry's answer machine. They thought it was so funny that they included it on the film.
Bruce Willis agreeing to guest appear on Friends for free, and because he lost a bet to Matthew Perry during filming is an urban legend. People Magazine Star Spotlight 2000 states, "Willis agreed to a guest stint on 'Friends' simply because he and Perry thought it would be fun." News outlets mistakenly reported on the rumor. Willis was in fact paid for the role, including syndication runs, but donated the money to The American Foundation for AIDS Research, AIDS Project Los Angeles, the Elizabeth Glaser Pediatric AIDS Foundation, the Rape Treatment Center, and UCLA Unicamp for underprivileged children.
When Volkswagen was approached about a product placement in the movie for its new Beetle, they said they would only pay if a male character drove the car, because there are already plenty of women who want to drive the new VW Beetles. However, it was decided that it was such a perfect car for Sophie (Rosanna Arquette) to drive that they would use it anyway, even though Volkswagen didn't pay them.
The Biddles Jazz & Ribs club was named after legendary Montréal bassist Charles Reed Biddle. He appears in the nightclub scenes with his daughter, Stephanie, on vocals. Biddle passed away in 2003, and the club is now named House of Jazz.
When Matthew Perry is cutting the grass at the beginning of the movie, he's wearing a shirt with the crest of the hockey team, the Ottawa Senators. Matthew Perry spent some time growing up in Ottawa, Ontario.
At the time of the movie's release, many critics panned Rosanna Arquette's performance, claiming that she delivered her lines like a female Inspector Clouseau (Peter Sellers' character from The Pink Panther (1963) franchise). In his DVD commentary, director Jonathan Lynn stated that she worked with a dialogue coach and he was quite pleased with her accent.
At the start of the hit scene, an insert shot shows correct lock picking technique. Two tools are required: the pick for setting the locking pins to their unlocked shear line, and the torque wrench to hold the picked pins in place while turning the cylinder.
The blues song that plays as Oz arrives in Chicago and meets his friend at the Oyster Bar, is performed by Bruce Willis and his band. The harmonica solo featured in the song is played by Willis himself.