Rey Mysterio: Royal Rumble 2009
The winner of the 2006 Royal Rumble, Rey Mysterio, is no stranger to overcoming insurmountable odds. Whether it's because of his size or his sheer endurance in Rumble matches, Mysterio had previously won the 2006 Rumble from the equally disadvantageous #2 spot and in doing so, broke the record for the longest time spent in a Rumble.
By 2009, Mysterio was a solid main eventer. Demonstrating his considerable endurance once more, Rey Mysterio lasted an impressive 49 minutes before being eliminated by #30 entrant, The Big Show. Mysterio left WWE in 2014 but returned at the 2018 Royal Rumble.
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At the age of 47, the master of the 619 is undoubtedly in the latter stages of his career. Despite this, he remains an active member of the WWE roster and is currently in a tag team with his son, Dominick. A true Rumble veteran, Mysterio will compete in the 2022 Royal Rumble match.
Dolph Ziggler: Royal Rumble 2010 and 2013
Dolph Ziggler is another wrestler to have earned the dubious distinction of having entered two Rumble matches in the dreaded #1 spot. In 2010, Ziggler was still finding his feet as a superstar and lasted an unimpressive two and a half minutes.
By the 2013 Royal Rumble however, Ziggler had established himself as a main event level talent. Entering first again, The Showoff lasted almost 50 minutes and scored two eliminations. Over the years, Ziggler has floated between the mid-card and main event scene.
Today, Dolph Ziggler is a seasoned veteran of WWE and is firmly entrenched in the Tag division. Like Rey Mysterio, both Ziggler and his partner, Robert Roode, will compete in the 2022 Royal Rumble