#1 Brock Lesnar - 6 times
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Despite being criticized for his limited appearances in the WWE, Brock Lesnar still maintains his position as the biggest box-office draw in the company.
Having exceptional encounters with CM Punk, John Cena, Triple H, and The Undertaker, Brock Lesnar remains the undisputed king of SummerSlam.
The Beast Incarnate has not lost a single match when he's headlined the biggest party of the summer, with the exception of 2015 where he ended up fading out to Undertaker's hell gate.
His bout against John Cena in 2014 for the WWE Championship is regarded as one of the single-most dominating matches in WWE history, where the Mayor of Suplex City embarrassed the Cenation Leader.
SummerSlam 2017 ended up with the Universal Champion defeating Roman Reigns, Samoa Joe, and Braun Strowman in a fatal-4 way match.
The Beast is scheduled to face Roman Reigns this year, which could catapult his status as the only superstar in WWE history to have headlined 7 SummerSlam events.
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