Triple H has won twenty-four titles in the WWE and is a fourteen-time world champion, having won the WWF / E Championship nine times and the World Heavyweight Championship five times. He was the first World Heavyweight Champion, having received the title in September 2002, he won the King of the Ring (1997), the Royal Rumble (2002 and 2016) and was the second Grand Slam Championship winner.
Outside of wrestling he has made numerous film and television appearances. Since mid-2013 he has created a storyline in which he and his wife Stephanie McMahon act as despotic and unscrupulous WWE co-owners, justifying everything by claiming to do what is best for the business: the duo will become later known as "The Authority" and several other wrestlers will join it.
In an interview with Gorilla Position, Triple H discussed how his relationship with The Undertaker was in WWE initially.
Triple H on The Undertaker
“You really had to earn that friendship with him, you sort of had to earn that respect with him.
You had to get someplace with him. He wasn’t going to go out of his way to chit chat with you or make you feel comfortable. Even if you were at the same bar at night, he wasn’t interested, he’d say hello, but he wasn’t interested in hanging out with you to make you feel comfortable or make you feel like part of the team or anything like that" - Triple H said on The Undertaker.
“I never had met Kevin or Scott or Kid or Shawn, but I very quickly became friends with those guys over a period of time and that came with a lot of baggage. I think it came with a lot of baggage for Mark too. I don’t think he agreed with everything those guys did.
They were our top guys but I think there were a lot of times he saw things they did or said and was like, whatever, stirring the pot a little bit or whatever that is. I don’t think he understood how this new kid comes in, green, with some potential I guess, but all of a sudden’s he’s in with these guys, I guess, and he’s running with that crew.
I don’t think he got it. It took me a while to earn his respect. I remember one specific night where we were all night, I’d say hello to him but wouldn’t talk to him that much. I was on one end of the bar with a bunch of people, he was on the other end of the bar with a bunch of people, he kind of gave me the nod to come over there, he went off to the side where he was by himself, and I walked off to the side with him, we just started talking, and I don’t drink, but he ordered two shots of Jack and put them in front of us, and we talked for about 30 minutes or something like that about a lot of things, and he kind of gave me the nod and said, ‘You’re alright, man’ and we both did a shot of Jack and that was the ice breaker”.