You can't really compare Jake Roberts with Steve Austin. Austin was an "entertaining" character full of charisma and funny catchphrases and beer drinking and whatnot whereas Jake Roberts was far more psychologically demanding, I mean watching him slap Elizabeth or doing some disgusting, negative promos (they were PG which shows how far you can go even with that rating) I started to hate him, that's how good he was. He's the guy you would LOVE to get buried, and not because he's a bad performer, but because his character is the biggest asshole there is and he plays it so well that you stop caring about mic skills and talent, but focus about the pure character alone. Apart from Bully Ray, there is no single heel that I would consider a good performer AND would love to get buried nevertheless, it's like a lost art. Overall Austin still wins due to his overwhelming entertainment factor, but don't take anything away from Jake Roberts, he was really good.
Steve Austin had the better career and was waaaaay more influential to the business. But imo, Jake Roberts is much better in some other fields. Stone Cold was a great mic worker, but Jake Roberts is one of the, if not THE, greatest of all time. I liked his character a lot better, too. Not to take anything away from Austin. The gawd understands why someone would like Steve better.
I'm not a big fan of Orton's Viper character. He's probably a better worker right now than he's ever been, but he was a LOT better on the mic as the Legend Killer. He's still good, but if he had his in-ring skills today with the Legend Killer/Age of Orton promo skills, he'd be ONE OF the best in the world today.