#2 Edge - New Years Revolution 2006
Money in the Bank began as a WrestleMania match way back in 2005 at 'Mania 21, and after Edge made a shocking cash in on John Cena almost a year later, it was clear that the concept was here to stay. This came after John Cena managed to survive one of the most brutal Elimination Chamber matches in history, and it kick-started the reign of 'The Ultimate Opportunist' as a main event player, establishing what Money in the Bank would mean to the WWE for years.
Edge would go on to become one of the greatest performers in WWE history, and this is exactly the thing that propelled him to do it. Given how he was an upper mid card performer leading into this, it added to the shock. Obviously we've seen some great ones since, but the first was always the most shocking, until the next entry on our list came along.