Why? Because that decade was all about badasses doing EXTREME stunts. Jackass. xXx. Tony Hawk's Pro Skater. The whole parkour fad. This was where the kids were in the '00s, and Warner Bros. knew it so badly that the movie was already in pre-production by the time that Hawk got involved:
"I don't remember exactly how many times we met, but I do recall that the group pitching the project brought a lot of energy to every meeting. They set up storyboards illustrating the action-packed plot, and even had a cartoon-voice actor read lines from proposed scenes ... When it came time to have our last big meeting to finalize the deal ... they had the whole story fleshed out, and I liked what I heard. When the meal ended and we all shook hands, everyone was confident that we had the green light."
Warner Bros. wanted that sk8r street cred so badly that they were also (allegedly) willing to pay Hawk a million bucks for the privilege. But before they could complete the ensemble and hit up Bowling for Soup for a cover of "I Believe I Can Fly," Skate Jam (as it was known) was cancelled, on account of the massive box office failure of Looney Tunes: Back In Action.
The point is, Tony Hawk's Pro Skater Jam didn't fail because the market wasn't there. Sick stunts, a pop-punk soundtrack, and the prospect of seeing Lola Bunny dressed like a Suicide Girl? Our pubescent hearts would've exploded with joy. Likewise, Space Jam worked because it encompassed the two biggest cultural properties of the day: basketball and Michael Jordan. Space Jam 2 will draw a sizable millennial audience, sure, but that lack of mainstream appeal means that it might be doomed like the Cleveland Cavaliers during "The Shot."