#1 The Undertaker and Shawn Michaels (2008)
The Undertaker and Shawn Michaels were the final two in the 2007 Royal Rumble match, wrestling for a good chunk of time before the Deadman reigned supreme. It was the best ever ending to a Rumble match.
The following year started in that same exact way. The Undertaker was entrant number 1 and Shawn Michaels came out immediately afterwards. We were getting a repeat of the epic clash at the end of the previous Royal Rumble. These two had a lot of history together, but little did they know what would be in store for them collectively.
In the following couple of years, Michaels and 'Taker would wrestle classic show-stealers at WrestleMania. But for now, they were on opposite sides in January. 2008 is remembered as one of the greatest Royal Rumble matches in history, thanks in no small part to John Cena's shocking return and victory.
However, a big part of the 2008 Rumble's success is because of the epic beginning it had with both 'Taker and HBK. There will never be an opening pairing to a Royal Rumble quite like this one. The legendary status, the history and chemistry between the pair make the Undertaker and Shawn Michaels the best opening pairing in Royal Rumble history.