- Hostility on the Set:
- Tupac Shakur got into a heated argument with an extra and actually pulled a gun on him. The extra who was a member of the Playboy Gangster Crips and said that Tupac flashed gang signs at him with a gun in his other hand the night before. No other extras on set witnessed the accident. Tupac later said that he was high and too intoxicated to remember what was said.
- Janet Jackson requested that Tupac have an AIDS test before his kissing scene with her. He angrily refused.note In a 2011 Vibe magazine article about Shakur, John Singleton claimed that the whole thing was a publicity stunt concocted by Shakur, Jackson and himself. But producer Steve Nicolaides and Shakur's brother, Mopreme Shakur, confirmed the incident in the article.
- Playing Against Type: Tupac Shakur sheds his gangsta image to play a romantic lead.
- Production Posse: Regina King, Lloyd Avery II,Tyra Ferrell and John Cothran all appeared in John Singleton's other film Boyz n the Hood.
- Shrug of God: The sad news that Heywood is told over the phone is never revealed. According to John Singleton, he left it open for viewers to imagine on their own, but in the DVD Commentary, he mentions it might be something related to AIDS.
- Throw It In!: Tupac Shakur improvised many of his lines during the scene in which Lucky talks to Jessie in the salon.
- What Could Have Been:
- Ice Cube was offered the role of Lucky, but refused because he claimed that he was not at a point in his career where he would play in a romantic movie. Plus, he was comitted to Trespass.
- Jada Pinkett auditioned for Justice.
- A sex scene between Lucky and Justice was originally going to take place after they kiss for the first time while sitting next to the water. This was later cut out of the script.
- John Singleton had an idea for an intimate scene where Lucky goes to his cousin's wake and talks over the dead body, it didn't make it into the movie.
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