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1. His match against Chris Benoit for the World Heavyweight Championship. That's when he made history for being the youngest World Heavyweight Champion.
2. His Hardcore match against Mick Foley. That was his match where he proves that he's not another pretty boy in the back who can't throw down in the ring.
I will say his match at WM24 it had the biggest impact IMO. I took him more seriously after that, because i was so sure he was going to lose, but he retained that was good.
But my favorite match was his hardcore match with FOley at Backlash 2004, that made him
His match with Chris Benoit at SummerSlam 2004, that's when he was first crowned Champion and was named the "youngest" ever World Champion. That was his big break with the company and so it has to be Randy Orton's Finest Hour.
He had such a good feud trying to end Taker's streak and taking another 'Legend' out of the game but as it stands it didn't work. The match itself was a great match even with Orton trying to tombstone Taker and this really put Orton on the map.