5 Worst Wrestling Matches Of 1999

#3 King Kong Bundy & Jim Neidhart vs. Yokozuna & Jake Roberts - Heroes Of Wrestling

This spectacular failure was brought about due to Jake Roberts being unable to control his own personal demons. The original plan was for two separate singles matches. But before Jake’s match, he cut his now-infamous ‘you wanna play 21’ promo that clearly showed that he was completely intoxicated.

By the time Roberts actually got to the ring, even further nonsense ensued. Jake was so messed up that he barely did any proper wrestling when he was actually in the ring. He spent more time ‘interacting’ with the ringside fans, standing around looking like he would fall over if he got his by the slightest breeze, and playing with his snake (literally, he pulled his python out of its bag and made suggestive actions with it which forced the camera to cut to the audience, who looked on bewildered).

By the time the singles match between Roberts and Neidhart was supposed to start, Roberts was so drunk that the promoter had to book an impromptu tag team match on the fly. Even with two more (sober) heads, the match fell apart. It was so chaotic and nonsensical that all Roberts could do was take a pin and that’s it.

This match would’ve actually been funny if it wasn’t so sad. Roberts was at arguably the lowest point of his life at this point, so it’s heartwarming to see that he has actually made a comeback in more recent years.