#1 The Undertaker(1) and Shawn Michaels(2) (2008)

Royal Rumble 2007 ended in the best way, with two of the cornerstones of the WWE, The Undertaker and Shawn Michaels, engaging in inarguably the best closing sequence in the Rumble match history. WWE wanted to keep the momentum going for the 2008 Rumble match as well, and who did they turn to that year? Taker and Michaels.
When The Deadman was announced as the #1 entrant of the Rumble match, fans knew they were in for something special. After all, Taker had never entered a Rumble match so early, and was easily the favorite to win the match. When Michaels music hit merely moments later, every single fan in the Madison Square Garden went into a state of frenzy.
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Ignoring the two subsequent entrants in Santino Marella and The Great Khali, the two old rivals carried on with their acclaimed show closing clash from previous year for almost 5 minutes. In the end, Michaels successfully managed to eliminate Taker from the match, taking revenge for his heartbreak loss the previous year and ending two consecutive years of majestic performances by the two all time greats.
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