Iconic match: Chris Jericho vs. Chris Benoit vs. Shelton Benjamin vs. Christian vs. Kane vs. Edge, WrestleMania 21
The top 5 begins with one of the more recent entries onto this list: the Money in the Bank ladder match. While it may just be a multi-man ladder match, the prize at the top of the rungs has elevated this particular flavor into its own wonderful brand of chaos. 6+ men compete at once, all aiming to grab the briefcase suspended above the ring, a briefcase that grants them a shot at the biggest title in the land, whenever and wherever they want it. The Money in the Bank match itself has been home to memorable spots and some truly scary bumps (Sin Cara still hasn’t recovered from this one), but it’s the promise of a title shot that is most memorable of all.
First off, given that it is not (usually) for the title itself, the card is slotted with mid-to-upper-mid card performers who don’t normally get a showcase spot like this on pay-per-views, and that always leads to more risk-taking than, say, an Intercontinental Title ladder match. Secondly, the winner of this brutal dance gets a marquee moment when they do eventually cash in their title, as Seth Rollins demonstrated at WrestleMania 31. While not directly a part of the match itself, the anticipation and speculation around “When will he cash in?” seeps into the race for the briefcase. A gimmick match that not only entertains like no other, but also leads to another exciting moment in the near future? Not bad for a modified ladder match.