#5 Triple H (Summerslam 1999 & 2000)
The 1999 Summerslam was the first to be headlined by a Triple Threat Match. Triple H looked set to get a singles match against Stone Cold Steve Austin at the event, but he was derailed on that opportunity a few times before it became a Triple Threat with Mankind. Mick Foley walked out with the WWE Championship, but Triple H defeated Mankind the following night to win the gold.
The following year's Summerslam saw yet another Triple Threat Match for the WWE Championship, but this was one with a deeply captivating story behind it. Triple H's relationship with Stephanie McMahon was at the top of the card for almost a year at that point, but Kurt Angle got in the middle of the husband and wife.
A top AEW star just called one of his colleagues 'spoiled' and 'narcissistic' HERE.
This led to WWE Champion The Rock defending his title against Triple H and Kurt Angle in a Triple Threat Match. Mayhem broke out immediately with Triple H upset with Kurt Angle following Angle kissing Stephanie on the SmackDown before the pay-per-view. The Game hit a Pedigree on Angle on the announce table, which gave the Olympic Gold Medalist a concussion.
The Summerslam 2000 main event started out as a singles bout between The Rock and Triple H before Angle eventually joined the fray. It was The Rock who pulled out the victory, hitting the People's Elbow on Triple H to retain the WWE Championship. Triple H went on to headline the 2003 and 2012 editions of the summer spectacle.