4. It Was One vs. One
The match between Shawn & Razor is often cited as the first ladder match in WWE history, but the very first one was between Shawn & Bret Hart, which went untelevised. That match took place in 1992. It wasn't until 1999 that WWE held the first ladder matches involving more than two contestants. After that, the concept of the ladder match evolved, which would spawn into TLC and Money in the Bank matches of the modern day. Most ladder matches are now contested with multiple participants, and while that can make for exciting times, there's something a bit more special about a one-on-one ladder match. The tension of a ladder match seems to be greater when there's just two men in it. Only Razor Ramon could stop Shawn climbing the ladder, only Shawn could stop Razor. The crowd tend to cheer a little louder because there's only one guy to support. In a one vs. one ladder match, there's also two guys to do all the storytelling, and to take all the risks. In multiple participant ladder matches, the bumps get evenly spread - which is good for the health of the wrestlers involved - but it makes their performances less noteworthy. Shawn & Razor had only themselves to make the match spectacular, which is exactly what they did.