#5 Owen Hart (1996) - Eliminated 21st - 2 Eliminations
Owen Hart was a great wrestler of his time, his career would have been more prominent had he not have been overshadowed by his brother Bret's excellent in-ring career. In the 1996 Royal Rumble, Owen Hart came in as the 17th entrant to the Royal Rumble and lasted 20 minutes and 43 seconds, coming in one entry before the eventual winner Shawn Michaels.
Owen would eliminate Hakushi on his way into the final 10 before being eliminated by Shawn Michaels and Diesel. The rest of Owen Hart's 1996 was inconsequential, spending the first half as a part of Camp Cornette, but in the second half, he worked as a tag team with the British Bulldog to win the WWF Tag Team Champion.
Unfortunately, Harts promising career would be cut short after falling to his death at the WWF's Over the Edge Pay-Per-View a few years later.