10 All-Time Craziest Wrestling Match Stipulations

9. Jailhouse Match

It's little wonder that honest American cop The Big Boss Man and crooked Canadian lawman The Mountie would eventually run afoul of one another. When they did, though, extreme measures were necessary. At SummerSlam 1991 in Madison Square Garden, the two squared off in the first-ever Jailhouse Match, where the loser would have to spend 24 hours in a prison cell. The match itself was a standard (or substandard, depending on opinion) one-fall-to-a-finish contest that saw The Big Boss Man pick up the victory after avoiding The Mountie's caddle prod and nailing an Alabama Slam. After the match, the real shenanigans began. The screaming Mountie was put in the back of a police van and taken away. Later in the show, the crowd was treated to a skit where The Mountie was thrown into a cell and hit on by a stereotypically flamboyant prisoner. Homophobia and rape jokes disguised as children's entertainment? That all makes for a crazy stipulation.
 
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Scott Fried is a Slammy Award-winning* writer living and working in New York City. He has been following/writing about professional wrestling for many years and is a graduate of Lance Storm's Storm Wrestling Academy. Follow him on Twitter at https://twitter.com/scottfried. *Best Crowd of the Year, 2013