4. Kurt Angle vs Shane McMahon - King Of The Ring, June 2001
A lot of the matches weve covered so far are hard to watch whats more uncomfortable than seeing professional wrestlers bleed and break themselves in the name of entertainment? Well, how about non-wrestlers doing the same? Shane McMahon had already shown himself to be slightly unhinged after taking a couple of incredibly high falls from the side of the WWE TitanTron, but that didnt compare to the punishment he received at King of the Ring. Angle didnt exactly escape the match unscathed either (actually ending up in hospital once the show was over courtesy of a damaged tailbone). The latter half of the match included a sequence in which Shane was to be hurled through several panes of sugar glass, but Kurts back injury meant that he couldnt get the required power behind the throw to do so. That and the fact theyd bought the wrong type of glass. At the first attempt, Shane bounced sickeningly off the pane and landed on his head and neck. Angle reportedly wanted to skip to the finish of the match, but Shane insisted that they complete the move. It took Kurt five attempts to throw his opponent through two panes of glass, the last one headfirst. It left both men horribly lacerated, Shanes forehead in particular coated with blood. In a later interview Angle claimed that he had a blast, proving that wrestlers minds dont quite work the way a normal humans does.