The story of how "White Men Can't Jump" got made is an interesting one, and certainly worth looking back on given the upcoming remake starring Jack Harlow and Sinqua Walls. From the fact that Keanu Reeves auditioned — and failed miserably — for the role that would eventually fall to Woody Harrelson, to the fact that Wesley Snipes was, by all accounts, very bad at basketball, it's almost amazing that the film was not only a success but has had a lasting legacy as one of the best movies about roundball ever made.

A big part of that is due to the chemistry between Harrelson and Snipes, who have been connected over the years going all the way back to the 1986 high school football comedy "Wildcats." Their performances as Billy Hoyle and Sidney Dean, and the way that their real-life friendship pops in every scene they share, have helped "White Men Can't Jump" endure as a sports movie classic. But there was a third lead in the movie who writer and director Ron Shelton had a much more difficult time getting a handle: Billy's girlfriend, Gloria, who was played by Rosie Perez.

Shelton didn't have much trouble writing most of the movie, recalling in a 2017 Entertainment Weekly article that he churned out the first 37 pages of his script in a single night. But Perez's character flummoxed him a bit, as he struggled to keep her part of the overall story. And then, thanks to a conversation he overheard, everything clicked.

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Writing women as characters who exist outside of how they relate to the male characters has always been important to Shelton, as evidenced by the way he crafted Susan Sarandon's character in the baseball classic "Bull Durham." But while he tried to come up with a way to make Gloria her own person, she was so closely tied to Billy that for awhile, she seemed to simply be an extension of Harrelson's character. As he explained to Entertainment Weekly:

"I was trying to figure out what Gloria's [Billy's girlfriend] thing was. It had to be so unconnected from the guys. Because that's big for me, to make sure that the women aren't defined in terms of the guy business."

Fortunately, a bit of light eavesdropping saved the day when Shelton heard someone mention that they had a friend who really wanted to be on "Jeopardy!" That was all it took, and suddenly Gloria had her own purpose in the film. In the movie, Billy and Gloria are on the run from a couple of mobsters to who they owe money from a gambling debt. While Billy is trying to hustle the money in street ball games around Los Angeles, Gloria has her own plan: she'll go on "Jeopardy!" and win enough money to get them free and clear. Thanks to Shelton's good fortune overhearing the right conversation at the right time, the character — and the movie — finally came together.

"There's no logic to it," said Shelton. "It's sort of the Hollywood dream."

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