- Acclaimed Flop: The movie was initially a Box Office Bomb despite high critical praise, though this was probably due to it being shown on only 226 screens. The film did make 70% of its total cinema gross from international showings, however.
- Awesome, Dear Boy: Val Kilmer met Robert Downey Jr. for the first time at a Hollywood party. A week later, he received the screenplay for this film, and agreed to do it before he'd even finished reading it. Upon agreeing, and much to his delight, he was informed that Downey had already been cast.
- Career Resurrection:
- Shane Black spent nearly a decade away from Hollywood after the failure of The Long Kiss Goodnight, after attaining a reputation as one of the industry's hottest screenwriters for his Lethal Weapon script and the Witty Banter style that became his trademark afterwards. This film (which also served as his directorial debut) put him back on the radar, before he directed Iron Man 3 eight years later. After that film became a billion-dollar grossing success, his follow-up film The Nice Guys became a Cult Classic.
- This film arguably marked the beginning of Robert Downey Jr.'s Hollywood comeback after the drug addiction that had ravaged his career. A few years later, Iron Man was released and proved conclusively that Downey was back on the A-list. Jon Favreau has even stated that he specifically wanted Downey after seeing him in this role.
- Creator's Favorite Episode: This is Robert Downey Jr.'s favourite movie of his own.
- Dawson Casting: As noted by one critic, Harry and Harmony are meant to have been in the same class in high school, but Robert Downey Jr. was 40 at the time of shooting while Michelle Monaghan was only 29. Their characters' ages split the difference; Harmony specifically says she's 34.
- Dyeing for Your Art: Val Kilmer had to quickly lose the fifty pounds gained for his plump role in Alexander, in order to play his fit GQ character for this film.
- Method Acting:
- Val Kilmer, after initially losing 50 pounds to play Gay Perry, then took to wearing nail varnish and a $500 pair of Louis Vuitton driving shoes to get into the character.
- According to the DVD commentary track, Robert Downey Jr. had one of the director's assistants crouching off camera jabbing him in the kidneys during the Electric Torture scene.
- Real-Life Relative: Robert Downey Jr.'s actual son Indio Falconer Downey plays Harry as a kid.
- What Could Have Been:
- Early in production, Warner Bros. considered Benicio del Toro for Harry and Hugh Grant for Gay Perry.
- Johnny Knoxville was set to star as Harry Lockhart.
- Working Title: The film was originally titled You'll Never Die in This Town Again, then L.A.P.I., then Bang!. Val Kilmer suggested to Shane Black that Kiss Kiss Bang Bang would have more appeal.
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