#1 Triple H - 7 times (WWE Backlash 2000, 2001, 2002, 2004, 2005, 2006, 2008)

Triple H. Cerebral Assassin. The Game. The King of Kings. Vince McMahon's Son-In-Law. Ok...that last one was more tongue-in-cheek, but you get the picture. Triple H has always been front and center of the WWE product. Working both as a heel and a face in his several years with the company showcases the quality of his work provided.
He has played both a cowardly heel and an avenging hero. He has fallen to Immortals and endured. There was a reason why Mr. McMahon would keep going back to this dependable WWE Superstar. Despite all the criticism that Triple H booked himself into high-value spots, no one in the whole wide world can take away his talent, charisma, and attractiveness as a top-level star.
Did you know a top WWE Superstar just wrestled outside the company? More details HERE
His work on the NXT product is indicative of his knowledge and commitment to the business. Triple H's legacy has already been written, and the Backlash PPV is a clear indicator of that. Would another Triple H match at Backlash ever happen? Never say never in WWE.