For promotional purposes, WCW head writer Vince Russo wrote for David Arquette to make many guest appearances and win the WCW World Title on an episode of WCW Thunder (1998). Most people called this the worst move in WCW's history and the final nail in its coffin, before going out of business in 2001. Arquette himself even admitted that it was not a good idea.
Around the time of this movie's release, David Arquette made a string of appearances on WCW television. In lieu of spending any of the money paid to him from WCW, David instead chose to give all of his WCW earnings to the family of deceased wrestler Brian Pillman.
Oliver Platt accidentally struck Randy Savage in the face during the filming of a fantasy scene. The footage of the incident, which was shot over Savage's shoulder, can be seen in the blooper reel shown during the closing credits.
The scenario of Jimmy King getting screwed by Titus Sinclair was based on a real life issue between Eric Bischoff and Ric Flair. In April 1998, Flair was fired from WCW for allegedly no-showing the taping for the April 16th edition of WCW Thunder (1998). By the end of the year, Flair was back in WCW after filing a lawsuit against Bischoff.
Jimmy King losing the title, when he was supposed to have won, is a spoof of the infamous Montreal Screw Job back at the WWF Survivor Series (1997), in which Bret Hart was supposed to have retained the title from Shawn Michaels, but lost.
The character of Titus Sinclair is based on WCW Vice-President Eric Bischoff, who was originally going to appear in this movie as a fictionalized version of himself, but was fired from WCW before filming began, thus the character of Sinclair was created as played by Joe Pantoliano.
David Arquette was given the WCW World Heavyweight title two weeks after the release of the movie as a promotional stunt. He eventually lost the title in a cage match similar to the one at the end of the movie.
In the movie, the boys' home state is Wyoming as well as Sasha saying that she grew up in Cody, Wyoming. Eric Bischoff, the Vice-President of World Championship Wrestling during the making of the movie owned a home and lived part time in Cody, Wyoming.
At one point of the film, when the cop is going off on his son about people that ended up as failures because they followed their dreams, he mentions Michael Bolton. This is most likely a reference to how Bolton was once a hard rocker, and "sold out" to doing adult contemporary music.
The WCW World Heavyweight Title used in the movie is completely opposite to the actual title, color wise. The real belt was gold with silver inlays on a black leather strap; originally brown, but after years of use and being soaked, sweat turned it a darker color. The belt in the movie was mostly silver with some gold detailing. For example, the area that says "World Heavyweight Champion" has a gold backing with silver letters, where the original has gold letters and a silver background.
The trivia items below may give away important plot points.
According to an interview he did with YouShoot in 2013, Diamond Dallas Page said that he pitched an alternate ending for the film to Warner Bros. What would have happened was that after the triple cage match is over, and the end credits are just starting to roll, Jimmy King tells Gordie and Sean that he would see them at the bar, before heading back to his dressing room to get changed, only to see DDP waiting for him. Just as the two wrestlers look like they are going to fight again, they actually hug each other, with DDP forgiving King for throwing him through all three cages. Then, Sean and Gordie enter the dressing room and are shocked to discover that King and DDP are friends. DDP then walks up to the two and says "Boys, welcome to the business. Let's go have a drink!" which helps puts all their differences aside.
Perry Saturn, one of the two men who attacked Sal Bandini (Martin Landau) had left WCW before this movie was out in theaters. He would go to the WWF/E by January 2000 and be part of the Radicalz. Then later he had a sidekick mop named Moppy.