#3 Diesel (1996) - Eliminated 29th - 5 Eliminations
Kevin Nash, known during his original run as Diesel, would enter the 1996 Royal Rumble from entry number 22, before being eliminated last by his former friend Shawn Michaels. Nash would later leave the WWE and infamously join their biggest rivals WCW that same year.
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Diesel, a former WWF Champion at the time would spend 17 minutes and 51 seconds in the Rumble match of that year before finishing as the runner up to Shawn Michaels. During the match, Diesel eliminated Tatanka, the Ironman of the 1996 Royal Rumble Hunter Hearst Helmsley, Owen Hart, Duke Droese, and Kamala. After eliminating Kamala, Shawn Michaels delivered a Superkick to the giant Diesel and knocked him backwards out of the ring.
While Diesel would end up on WCW TV, an imposter Diesel would appear at the 1997 Royal Rumble, and Nash himself would reprise his Diesel gimmick at the 2011 Royal Rumble. 15 years after he last performed in the Rumble as the Diesel character himself.