Lupe > rat face, easily.
And the fact is, Lupe coulda easily been in jail with Chilly, it's supposedly all kind of audio with him talking in codes that was being used in trial. It ain't about whether he was superthug or not...it's about the fact that despite the little hints about the game in his early music sounding pretty authentic, he has pretty much shied away from incriminating himself and setting the tone for the Hip Hop task force to even look his way by fronting or flexing about his past.
Most rappers start off rapping about normal shyt and then pick up the thug image for sales and attention...Lu went in reverse, to the point where you have people saying he should go back to the gangsta shyt. Now i'm sure this has to do with the fact that he's creative enough and conscious enough to not have to but it partly seems like he went that route out of necessity. If FNF was indeed started with drug money it would dumb as fukk to be flagrant about your activities WHILE being investigated. You can't compare that to Jay and his situation.
Keep in mind that this nikka:
Probably moved more weight than most rappers who talk about it on wax.