I'm sure it was mentioned but Dynasty Intro...top 5 Jay verse IMO. A couple songs on Dynasty had a darker sound than usual for him actually, This Can't Be Life, Soon You'll Understand, Where Have You Been...dark might be subjective, maybe more more wistful/melancholy sounding...
There's Been a Murder also has to be one of the darkest songs he ever recorded
I kinda wish he had done more songs in this direction