Orton's biggest problem was nailed by
Choke2Death, he hasn't really been in a legitimate feud since his big time feud with Mark Henry. Orton at the moment has no direction with his character, and I feel that is hurting my investment in his matches recently as he just seems like another one of the bland guys that WWE is throwing at us lately.
I was talking to my friend about Orton the other day and we got into a very interesting discussion. He pointed out the fact that it seemed like Randy's position with the company hadn't changed at all since he won the belt the first time, and in terms of "getting over" , Orton had been given more world titles undeservedly than any other champion in history. As an Orton fan, I'd actually come out and agree with this statement wholeheartedly.
Randy's in-ring work has become more consistent now, but his character has really been suffering since he changed up his look and his theme song (his BETTER one

) in 2008. Randy has never really had that big "OMG MADE" moment like a killer promo or that one big
***** match to make him an all time great, which is why sadly he'll be stuck a few tiers below (despite what WWE may tell you) when it's all said and done.
Orton's almost like a poor-man's HBK in a sense that when he stopped incorporating his real life tendencies into his work (I.E. being a cocky asshole who believed he could sleep with any woman, beat anybody, be on top of the world, etc) he became stagnant as a character, and to try to build ORTON of all people into a serious "viper" , an individual who dissects people.... Just never ever seemed believeable to me.
For the record, I think Orton works MUCH better as a face with his current gimmick.