Okay, I really haven't seen much Sentai so I'll skip that.
As for Rider, I think I have to go with Ryuki. Faiz was pretty bleak and dark, while Black did have a lot of unhappiness going on with Nobuhiko, but I think Ryuki has to take it. No other show is founded on the premise of a madman gathering together a group of psychopaths and sociopaths to murder each other in his crazy mirror world from which monsters routinely attack and devour normal people - all so that he can ultimately kill whichever one is left and steal his life force to save the madman's sister. That is one dark freaking premise.