#4 Hardcore Evening Gown Match - WWE King of the Ring 2000
WWE recognizes Pat Patterson as the first-ever Intercontinental Champion whenever the title's prestigious history comes in play.
But the same man who was the inaugural Intercontinental Champion also took part in WWE's "Evening Gown Match", a stipulation which was usually reserved for Divas back in the day.
After a backstage incident, Vince McMahon had announced that Patterson would defend the Hardcore title against Gerald Brisco in a "Hardcore Evening Gown Match" at King of the Ring 2000.
As you might have guessed, two 50+ aged veterans dressing up as women and attempting to strip off each other's gowns was as embarrassing as it sounds. Due to the 24/7 rule in effect, Crash Holly intervened and pinned Patterson to become the new Hardcore Champion.
The 24/7 rule has led to some of the most bizarre WWE moments in history, but Patterson and Brisco's Hardcore Evening Gown Match was just too strange and cringeworthy for its own good.
Thankfully, we now live in an era where both male and female WWE Superstars won't resort to tearing apart each other's gowns for the sake of this unusual stipulation.