In 2009, Randy Orton became the first true heel in 10 years to win the Rumble match (while officially being a heel in 2005, Batista was already being cheered before the match).
In addition, Orton was the first in 16 years to do so at main event WrestleMania. As of today, he is the last Rumble winner to close WrestleMania.
Despite having an awesome buildup to his match, which saw him take out the McMahon family, he couldn't overcome WWE champion Triple H at WrestleMania XXV. This didn't matter so much, however. He won the belt at the next event, Backlash.
Orton's title reign went on for two months before losing to Batista. But this would be brief. He regained the belt eight days later.
Throughout autumn Orton traded the belt back and forth with John Cena before being displaced at Bragging Rights.
Shortly after, Orton turned face and grew into one of the top stars in WWE today.
If you are wondering why Orton gains the top spot on my list despite losing his match at Mania, I'll give you my answer.
Before winning the Rumble, Orton was struggling to get back into the title picture. He injured his shoulder the year before, wasn't getting the usual comeback treatment and was stuck in irrelevant feuds with mid-card wrestlers.
Even though he lost the big match and failed to have a significant run with the title, he managed to stay relevant in the main-event scene for almost a whole year.
Orton had none of the special cards that allowed others to be propelled into the main event quickly and none of the setbacks to halt his push.
Unlike Triple H and Rey Mysterio, he was not riding a wave of momentum caused by pity or a comeback.
Staying healthy meant he had a longer run of main events in comparison to The Undertaker and Batista.
He was treated with more respect than Chris Benoit, who was taken off the main event card whenever he wasn't facing a member of Evolution.
Unlike Brock Lesnar, Orton wasn't given any special treatment to keep him sweet to stay in the company.
Unlike all the other wrestlers in the past 10 years, Orton worked hard for his win and continued to work hard over the following year to maintain his spot.
The others may have done well, but Orton simply did better.