Actually, character really doesn't sell compared to perceived quality and utility. Character only sells in the high end and in niche vehicles.
The problem is that Chrysler, GM and Ford have to sell mass-market products to stay in business.
The Challenger is not what the car would have looked like if it remained in production. It is a near identical copy to the '70 (plus some larger wheels.) Actually, it is a dead-ringer for a full-sized version of the Hot Wheels '70 Challenger with oversized mag wheels. If it would have remained in production with a decent design team, it would have a more streamlined, yet still edgy look.
I'm not sure that one can call a Challenger a "risk." Essentially, this is lemming-like. First the VW New Beetle and PT Cruiser, then the Mustang, GT, then Charger...this is just the logical progression. The Camaro will return looking like a '69 in a couple years (after the retro crazy peaks) ... mainstream sedans and minivans will be neglected (as usual,) and everyone will wonder why Toyota is number one, amd GM and Ford are in bankruptcy protection.