I love a lot of his matches on his first DVD. HE had a good match with Vader in WCW. And decent matches with Sabu and Dreamer in ECW.
The Mind Games match is pure awesomeness IMO. He makes HBK look incredible; it was just a pity that the ending stinked. That was a fued that I would loved to have seen happen 10 years ago.
The HIAC is unmatched, nothing will ever happen like that ever again. Absolutely amazing, incredible, cringeworthy, historic. I do wonder whether it is a bit of a shame that he will be remembered for this one match.
He had some great encounters vs the Rock, though I believe the ten successive chair shots in that Rumble I Quit match was a bit much, especially as he knew his kids were there.
But I think his best match may have been Cactus Jack vs HHH at 2000 Rumble, the street fight. I reckon it may be one of the best street fights ever. (Their HIAC wasnt bad either, but the WM main event was a let down, especially when he flopped on that elbow drop, it was a match which didnt heat up until he and Big Slow got eliminated.)
Since then though, he has only had two matches which were worth a damn. I believe he helped Orton and Edge like no one else in the business could. There were absolutely superb matches of their type and are only second to the HHH street fight.
I would like to see him do well in TNA but he needs to stay out of the ring. His mike skills are good enough to do well and help someone there. If he gets in the ring he may let himself down.