I don't know if there has been any specific peak in skateboarding, but all I know is that the early 2000's were my favorite time for skateboarding so far.
We got Dying to Live, Yeah Right!, Sorry, Really Sorry, In Bloom, Sight Unseen, Menikmati, Modus Operandi, Baker2g, Label Kills, Chomp on This, One Step Beyond, This is Skateboarding, DC Video, Almost: Round 3, That's Life, Chichagof, Baker 3, Elementality, etc....
Insane.