I wonder why popular culture embraces thieves, assassins, and slavers (pirates, ninjas, and pimps) and raises them to a level of cool

It's that entrepeneurial spirit, of course! If dominant popular culture used a totemic value system (such as has been popularized about several native cultures), we might be inclined to hunt down and eat the hearts of these very icons of adulation! You know, to ritually absorb that entrepeneurial spirit.