Roberts did up his game on the mic and character wise around 1990, it was the DiBiase feud that was kind of a lightning rod for him, if you watch that Wrestlemania 6 promo (which many consider in the top 3 ever) you can see that's the point all the pieces came together for him. Prior to that his feuds had great potential but never really lived up to the hype, Honky Tonk Man was a forgettable match and the Andre match was an abortion.
The only time it ever really worked was against Rick Rude and even then, Jake never really seemed to get anything from it as it was Rude who got pushed to the IC title. After that though Jake's off screen demons and issues with Vince (he had been "promised" a spot on creative that he never got, hence him holding up Vince at Mania 8 for his release) clouded things for him and he never lived up to that potential. Jake also suffered from the "gimmick wrestler's curse". Anyone with a physical gimmick (snake bag, nightstick, shears etc) would have had to lose that gimmick to have a belt and the belt would not be sufficient replacement. If Jake had had a belt, he'd have had to parade it and that would have taken Damien out of the mix or make things too convoluted.
As for the Snake Plisken analogy, I don't really see it, Jake never played an anti-hero, he came in heel, became a stand-up face and then went out and out heel again. Steve Austin was clearly similar, but when Jake went heel against Savage, it was more of a Nicholson Joker or Hannibal Lector vibe rather than Snake Plisken.
