Shelton Benjamin is possibly the most synonymous name attached to the Money in the Bank match and although he never ever won it, he's had the most unforgettable moments in its history. Wrestlemania 21 was the stage for the first ever Money in the Bank match and Benjamin set the tone for what fans could expect to see in future matches. As Chris Jericho was attempting to unhook the briefcase at the top of the ladder, Benjamin proceeded to run up a ladder and clothesline Jericho off the top of the other ladder it was stacked up against; a truly phenomenal athletic feat.
4) John Morrison's ladder moonsault
John Morrison is another star who thrived in the Money in the Bank match without ever winning it, as his athletic ability made him a dead cert to be included in the contest. Wrestlemania 24 was one of the best editions of the match we have ever seen and one of the finest moments came as all the competitors were fighting it out outside the ring. John Morrison would proceed to climb up the turnbuckle and with ladder in grip, moonsault on to everyone on the outside.
3) Shelton Benjamin's leap of faith
Appearing again on the list, Shelton Benjamin is one of the main reasons why this match became so special and he really helped to make it popular in its early years. At Wrestlemania 25, Shelton literally took his spots to new heights. Climbing atop a huge ladder in the middle of the entrance ramp, most people were confused as to what Shelton had in mind. With all the other participants fighting it out below him, Benjamin would perform a senton flip onto everyone in what appears to be a sickening landing for him but he was fine thankfully.
At Wrestlemania 23, the Money in the Bank match included two men who were no strangers to ladder matches at all so it was only fitting Jeff Hardy and Edge provided one of the matches most memorable moments. As Edge lay motionless on a ladder stacked between the ring and barricade on the outside, Jeff would leap from a huge ladder of his own onto Edge and crash right through the ladder. The move must have took years off both Edge and Jeff Hardy's career in what was one of the most impactful spots we've ever seen.
1) Shelton Benjamin crashes through a ladder
It is only right that the top spot of this list goes to Shelton Benjamin, someone who has provided so many moments throughout the match's history. Wrestlemania 24 is the scene for his most insane stunt. Shelton found himself at the top of the ladder, just one occasion of many where fans thought he would finally win the match, but Carlto and Mr Kennedy would catch up with him and push him off the ladder sending him crashing through another one on the outside. Shelton makes every spot look truly fantastic and performed one of the most painful looking spots ever seen with incredible grace. Carlito and Kennedy's shocked faces sum up just how insane this moment was.