#2 Triple H (WWE SummerSlam 1998)
Triple H's victory over The Rock in this ladder match from WWE SummerSlam 1998 match marked the beginning of two main-event runs for a pair of future icons. So it's an invaluable piece of wrestling history. While The Rock wrestled as a heel in the contest, Triple H was the face challenger for the former's Intercontinental Championship.
Even though The Rock was still early in his WWE career, he had already shown his versatility with his new heel character. "The Brahma Bull" was already becoming a top star.
On the other hand, Triple H was trying to break into the upper-card scene. By the end of the match, he solidified his position as a force to reckoned with in WWE. While the bout itself was a great back and forth contest, Chyna's involvement in the ending sealed the outcome in Triple H's favor.
The match is rightfully considered as one of the best ladder matches in history, and it is fondly looked back on by the WWE Universe.