#3 Shelton Benjamin (Tied, 5 Appearances)
We go from the creator to The Gold Standard.
Tying Chris Jericho's five appearances is a man who also competed in the debut of the stipulation- Shelton Benjamin. Competing in the 2005, 2006, 2008, 2009 and 2010 MITB matches ensured that Shelton's legacy within WWE was intact and will always be remembered.
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A naturally talented, gifted high-flyer; the man who's theme music stated he can't be stopped definitely proved it through his death-defying stunts throughout his, albeit, unsuccessful attempts to secure the victory. When people mention the match-type, two of Benjamin's spots may come to mind.
The first being, in the debut match, where Shelton ran up a ladder almost vertically that was leaning up against the ladder Chris Jericho was using to try and reach the briefcase. Several years later, at WrestleMania again, Benjamin somehow eclipsed this ridiculous act of athleticism when he hit a terrifying dive atop a monstrously tall ladder on the outside to the rest of the competitors within the match.
Despite never getting to wrap his hands around that golden ticket, Shelton Benjamin will live long in the memory of the Money in the Bank stipulation as, many would argue, without his daredevil acts, the match type wouldn't have gotten over as fast.