The SRT8 is awd, and automatic, so how is that any more/less skillful than just going from a roll? Step on the gas and go. It's the exact same thing. The most fair way to run this race is for the Cobra to be on DR's, and the SRT8 on it's street tires (b/c it's awd), and then run from a dig. At the track would be best too. How much power the Cobra makes is irrelevant though, because more rwhp on the street, on normal street tires, and rwd, it's more of a handicap than help. I've driven my friends SRT8 (300C) at the track, and it ran pretty well. It's a far cry from what people consider a "stock 300C" or "stock Grand Cherokee" in this case.
As far as running from a roll is concerned, it's just to prove which car has more balls, simple as that, which is why many runs take place from a roll. Just to prove who has the more powerful car (which is the standard debate most of the time).