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#7 Shawn Michaels - Royal Rumble winner (1995 & 1996)
Shawn Michaels made history with his first Royal Rumble win in 1995. The Heartbreak Kid started at the No.1 spot and lasted until the end. Just when it looked like The British Bulldog would win, Michaels brought to light a key rule in the Rumble by skinning the cat and only allowing one of his feet to touch the floor before returning to the ring to eliminate Bulldog.
In 1996, Shawn Michaels returned to the Rumble as a different man. He was no longer the cocky villain that the fans hated, but now a courageous hero that they rallied behind.
HBK came in at No.18 this time, but he still lasted until the end. Michaels eliminated his best friend Diesel to win back-to-back Rumbles. This time, he also went on to WrestleMania and won the WWE Championship.
#6 Triple H - Royal Rumble winner (2002 & 2016)
Triple H made a triumphant return from a quadricep injury at New York City's Madison Square Garden and entered himself into the 2002 Royal Rumble Match. He used this momentum to outlast Stone Cold Steve Austin, Mr. Perfect and Kurt Angle to win. The Game went on to WrestleMania X-8 and defeated Chris Jericho to win the Undisputed WWE Championship.
The King of Kings made history 14 years later when he had the biggest gap between Rumble wins. After being attacked and taken out by Roman Reigns, Triple H returned in the 2016 Rumble.
He got revenge by eliminating the then-WWE Champion Reigns. This left the Game and Dean Ambrose with the title on the line. Triple H eliminated Ambrose to win his 14th world title.
