The early 90's for sure with Pamela Andersons (the leaked tapes) and Jenna Jameson etc. but if my memory serves me correct, the early '00s was the era of "bearly legals" and "pigtails" with porn actresses like Aurora Snow, Adrian Sage and Gauge. Those where the types that ruled until Bree Olson came and fused the two styles.
Yeah, that was kinda weak. That crew should have been the last group of guys to enter a business deal with. But i feel bimbo Ash is just a walking silicon bag of bad decisions.

To get that far, you have probably even done worse decision like joining the crappy gang(with all that entails), or even worse deal with Arthur.