In high school, we all knew or know a person like Jeff Hardy in real life. He seems like a genuinely nice, artsy-fartsy guy. He goes with the flow and doesn’t seem to have heat with a single soul because he’s just that soulful and cool. The ladies think he’s cute and the guys want to hang with him.

RELATED: Matt Hardy And Jeff Hardy Are The Rare Siblings Who Were Bad RivalsAthletic enough for the jock crowd, certainly freaky enough the alternative crowd, and evidently tough enough to stand tall against Deadman Inc. and earn Big Evil’s respect in a Ladder Match for the WWE World Championship on Raw. It took a few more years for The Charismatic Enigma to finally win the big one, but when you earn the respect of The Undertaker, you definitely are a made man in the WWE.

How Jeff Hardy Vs Undertaker Came To Be

Not thinking the Hardy Boys were extreme enough, Jeff Hardy picked a fight when he actually targeted The Undertaker. For his crime, Taker handcuffed him and kicked the heck out of him. Several weeks before their now mythical ladder match, The Deadman was watching Jeff Hardy take down Raven. After the victory, The Undertaker — the world champion — intimated that he had his eyes on the Charismatic Enigma.

One week later was the same week as McMahon’s 'Ruthless Aggression' promo. On this night, McMahon also booked a match between The Phenom and Hardy, to which Taker was more than willing to make the kid famous. Jeff Hardy knew full well this was his chance and told Matt he was going to become a singles star or die trying. In the non-title match, The Undertaker throttled Jeff. As Taker was almost out of the arena, Jeff dared to challenge him for the Undisputed title in a match where he could actually win, a ladder match.

The Match Between Hardy And Undertaker Was Built To Perfectly

The night of the match, July 1, 2002, Jeff Hardy was readying himself by climbing all sorts of rigging in the back, reminding the fans watching that he’s been in tons of ladder matches and Taker’s been in none.

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That gave him the confidence to live for the moment and later in the night, a video package was shown to showcase the madness and the magic that Jeff Hardy creates with ladders. JR and The King hyped the match up and did their job — they made you believe that the kid might have a chance. Even Lita, recuperating from neck surgery, had come to wish her friend good luck.

“Make Yourself Famous”

Jeff started the match out quick and managed to get even more under Big Evil’s skin by messing with his motorcycle, and got a quick early advantage thanks to a ladder and a chair. It wasn’t before long though that Taker took charge for a moment. Hardy was able to attack and keep coming at the Undisputed Champion with ladder, but it didn’t take long though for The Undertaker to take complete control and practically obliterate Hardy. He would leave The Charismatic Enigma in a heap, but Jeff still wouldn’t stay down. Jim Ross’ commentary for this match ranks right up there with any big match he ever called pulling for Hardy. After his defeat, Hardy screamed at The Deadman, “I’m still standing!” But instead of annihilating him, the big nasty heel champion raised his defeated challenger’s hand.

It would take six more years, and some stops and starts due to Jeff battling his own personal demons, but at Armageddon 2008, all of the good will that Jeff Hardy had built up with fans around the world paid off with a momentous ovation when he was able to topple both Edge and Triple H and become the man, once again with Jim Ross on top of his own game. “From daredevil to champion! From enigma to icon!” he exclaimed as the fans in Buffalo celebrated with the new WWE champion.

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The Rainbow-Haired Warrior has always been the epitome of a guy who is over just by being himself and doesn’t need the title. Which is why when he finally claimed the gold, it was a big time moment. He’s so beloved by throngs of fans that the name value always keeps him at the top, he just needs the brass to get behind him as well and there could even one last big moment for the Enigma. In a lot of ways though, this feud with The Undertaker was a big reason why Jeff became a top guy.