The idea of in the 90's to 2000's was a wild time for these two as Velvette wouldn't be in their lives till the 2010s.
list of headcanons below
Vox getting movie ideas and info from new sinners as the internet was lacking and tv reigned king. The porn studio doubling as a movie studio to make bootlegs of living movies/tv shows.
Vox finding the whole concept of Austin Powers being 'extremely sexy' hilarious just to get blackmail of val in the costume. Probably lying that it was a serious film. This backfiring when one of vals workers told him it was a comedy.
Not sure when they would make their big break into Overlord status. i kinda see them as skating right under till Velvette. Owning large portions of territory but, just a bit too dumb between the two of them how to fully organize it's full potential.
Vox overthinking and Val underthinking; ' lets just shoot bitches.'
Which leads to very VERY questionable and cringey marketing tactics of the 2000's. Vox was more than happy to going back to being dapper and gaining 'nostaglia'/'modern marketing post 2000's
I also think this is around when Val got his piercings as body jewlery surged during his era.