When Woody Harrelson was making this movie, the producers hired Bob Lanier, the retired Detroit Pistons' center, as a basketball coach. Harrelson, who had played some basketball in college, was bragging to Lanier about what a great player he was. Lanier invited Harrelson to play a little one-on-one. Harrelson later described it as "the most embarrassing 15 minutes of my life".
Charlie Sheen was the first choice for the role of Billy Hoyle. He turned it down, saying "I didn't feel it would be any fun. I don't feel connected to basketball. At least, when I do a baseball movie, I know I'm gonna have a good time."
The musical R&B quintet Riff recorded a song and accompanying music video called "White Men Can't Jump" for the movie. The music video featured Woody Harrelson, Wesley Snipes and Rosie Perez. It can be seen on the DVD release with bonus features.
Marques Johnson has a supporting role as Raymond, who loses a game to Snipes and Harrelson. Johnson was a star player for UCLA's 1974-75 national championship team coached by John Wooden and later played for the NBA's Bucks, Clippers and Warriors.
When Gloria and Billy are about to leave to see Sidney about the money he swindled from them, Gloria goes to the closet to put on a jacket. In the closet on the top shelf is the board game for Jeopardy, based on the same game show that Gloria is continuously attempting to get on to.