Hunter Hearst Helmsley made his WWE debut within the year 1995, portraying the character of an aristocratic sophisticate. Eventually, the character would evolve into the crude prankster Triple H, pioneer of D-Generation X, followed by a solo act as an overwhelming metal badass, and afterward, a suit-clad authority figure who takes portion in marquee matches from time to time.
Triple H can effectively be considered one of WWE’s most successful heels, but he’s had many babyfaces runs during his career as well, not to mention lots of awesome matches along the way.
5. Babyface: The Rock vs. Triple H (SummerSlam, 8/30/1998)
This SummerSlam ladder match for the Intercontinental Championship went on right before the Steve Austin/Undertaker World Title primary event was overseen to take the show. It’s a fun match between two wrestlers on the cusp of fame who finished up getting the swarm super energized for the match in spite of a need for the tall spots that ordinarily characterize ladder matches. Other than being an extraordinary bout, this match was a significant minute in Rocky’s transition from an astonishing heel into an adored babyface.
4. Babyface: Chris Jericho vs. Jeff Hardy vs. John Bradshaw Layfield vs. Shawn Michaels vs. Triple H vs. Umaga (No Way Out, 2/17/2008)
Of all the contrivance matches WWE cherishes to engage infrequently, the Elimination Chamber is conceivably the foremost underrated. They’re full of action and wacky spots, like all multi-man matches, but with the added toy component of this silly playset to bounce off of and small units to keep the characters in. This 2008 match from No Way Out is especially fun, particularly after you get to the final extend where Jeff Hardy swims upstream against Triple H.
Must Read | Greatest WWE Matches Ever
3. Heel: Chris Benoit vs. Shawn Michaels vs. Triple H (WrestleMania XX, 3/14/2004)
This WrestleMania XX main event World Heavyweight Title match is considered by many fans to be one of the greatest triple threats in history. It’s got an awesome story with Chris Benoit as a fan-favorite underdog, pre-Daniel Bryan, proving himself against two of the biggest stars of WWE in Triple H and Shawn Michaels.
It’s the rare Triple H match that didn’t involve a massive burial, and the post-match celebration between Benoit and Eddie Guerrero is among the greatest emotional highs in wrestling history, if tragically bittersweet today.
2. Heel: Daniel Bryan vs. Triple H (WrestleMania XXX, 4/6/2014)
In the 21st Century, Triple H created a reputation for “burying” other abilities in order to keep himself on best, making him a disputable figure with numerous fans. But by the 2010s, Triple H was transitioning out of dynamic in-ring competition and into an administration position and overseen to recoup that terrible notoriety, beginning with the star-making “Authority” fight with Daniel Bryan.
The swarm favorite Bryan, in arrange to induce into the WrestleMania XXX main occasion title match, had to overcome Triple H at the very beginning of the appearance. And the match itself may be a banger, with Trips giving one of the finest exhibitions of his career to improving Bryan’s battle to reach the best.
1. Babyface: The Undertaker vs. Triple H (WrestleMania XXVIII, 4/1/2012)
Triple H’s second WrestleMania effort against The Undertaker was eventually overshadowed by not only the John Cena/Rock “Once in a Lifetime” main event, but the two Shawn Michaels/Undertaker classics of the previous years. All that said, this Hell in a Cell match is really one of the incredible passages in Triple H’s body of “epic” matches that a few fans contend are needlessly long.
Lasting over 30 minutes, it’s the longest match of “The Streak,” but it’s full of gigantic titan vs. titan pro wrestling drama, particularly with a recently retired Shawn Michaels as the guest referee.
