Producer Spike Lee believed the female lead should have believable basketball skills. Gina Prince-Bythewood said in an interview "I saw over 700 people for the part: actors, ballplayers, people who had never acted before in their life. It finally came down to Sanaa [Lathan] and Niesha Butler [a star player at Georgia Tech and 1999 Atlantic Coast Conference rookie of the year]. I put Sanaa with a basketball coach for two months and Niesha with an acting coach."
In an interview with the Los Angeles Times, Sanaa Lathan said her basketball tryout was terrible because she'd never played before. "It was so embarrassing because literally I didn't know how to dribble. I didn't know how to hold the ball. But I'm proud of how it looks [in the movie]. I had no idea I would be able to do it."
After playing a smooth-talking player in Waiting to Exhale (1995), Dennis Haysbert was hesitant to play another cheater. He told Jet he took the role because "Then I saw the emphasis was going to be on the father-son relationship. That was something that was close to my heart."
This is the second incident where Omar Epps has played a character named Quincy. The first being in 1992's Thriller/Drama Juice, starring Tupac Shakur. There, Epps plays Quincy 'Q' Powell as opposed to Quincy 'Q' McCall in this film.
Omar Epps and Regina Hall both have connections to Scream 2 (1997). Epps played the boyfriend of Jada Pinkett-Smith's character in Scream 2, whereas Hall played a spoof of Pinkett-Smith's character in Scary Movie (2000).