Playing off the recent rise in popularity of pro wrestling at the time, Bill Stone, president of Fosstone Productions organized what was intended to be a series of pay-per-view (PPV) events consisting of wrestling stars from the 1980s and early 1990s. Stone had three subsequent PPV shows (to be broadcast on a quarterly schedule) already in the planning stages if the first one achieved the break-even point of 40,000 PPV buys. Heroes of Wrestling only did 29,000 PPV buys, so Stone scrapped all future shows. In addition, Stone was furious with the lackluster show itself, and especially the antics of Jake "The Snake" Roberts. The show was critically panned and ridiculed by the wrestling press, with some going as far as calling it the worst wrestling PPV event ever produced. Heroes of Wrestling was declared a failure by the wrestling mainstream and was recognized as the worst major wrestling pay per view of 1999 by Wrestling Observer Newsletter and, throughout the years, has called the tag team match between the Bushwackers and Sheik/Volkoff one of the worst wrestling matches ever if not THE worst. Meltzer gave the match the number of Absolute Zero. Bryan Alvarez, of Figure Four Weekly, gave it "minus more stars than there are stars in the universe, and the universe is infinite".
The most memorable and controversial moment of the show involved the last match of the evening.
Heroes of Wrestling was supposed to feature a double main-event, with Jake "The Snake" Roberts scheduled to face Jim Neidhart in the first match while King Kong Bundy would take on Yokozuna in the other match. Before his match, Roberts was to cut a promo in which he was supposed to taunt his opponent that night, Jim Neidhart. Roberts showed up for the interview segment to set up the promo in a heavily intoxicated state, due either to alcohol or drugs. As the interview progressed Roberts became hostile toward his interviewer and struggled to finish his promo, but because he was so intoxicated, his words were slurred. The interview became infamous not only for its unscripted nature but for Roberts' only fully intelligible sentence, an attempted analogy about playing cards as the event was being held at a casino: "You don't want to play cards with me because I cheat. Okay? I cheat. You wanna play 21? I've got 22. You want to play blackjack? I've got two of those too!"
After the interview, Roberts walked to the ring with the snake he was going to use for that night's match. However, once he got to the ring, he put the snake down and walked back up the ramp. Roberts then walked back down, staggered around the ring to greet the fans, and then grabbed a female fan and had her rub her hands across his chest. He then pulled the snake out of the bag, stuck it in between his legs in a suggestive manner. began stroking it, then collapsed in the middle of the ring with the snake draped over his body and tried to kiss it with his tongue.
In an effort to salvage the match with Roberts in no condition to wrestle, the promoters announced that the match had been changed from a singles bout to a tag-team match, and sent out Bundy and Yokozuna to team with Neidhart and Roberts, respectively. Bundy defeated Roberts by hitting him with a splash after Roberts had staggered and fallen around the ring several times. The pay-per-view immediately cut out following the match as Roberts attempted to disrobe in the middle of the ring.
The show also suffered from changes to the advertised card. The billed Main Event, Bundy vs. Yokozuna, did not occur, and Gordon Solie was advertised as the show's commentator but did not appear due to declining health. Critics panned the performance of Solie's replacement, Randy Rosenbloom, who appeared to have no knowledge of wrestling whatsoever. During one match, Rosenbloom called a dropkick a "flying leg kick", and later as a "leg drop".
- Numbers in parentheses indicate the length of the match.
- The Bushwhackers (Butch Miller and Luke Williams) defeated The Iron Sheik and Nikolai Volkoff (8:42)