in terms of ..:
understanding the world and human history, best philosophical POV: Heidegger
getting how deep and complex human nature is: Cioran, Nietzsche, Schopenhauer
most creative philosopher, best guy to get inspiration from and look into the future: Deleuze
best philosophical system, creating a rational framework to make sense of the world: Spinoza, Hegel
best ethics: Jesus from Nazareth, Epictetus, Seneca, Pascal, Socrates
better marxist/materialistic point of view: Guy Debord, Raoul Vaneigem
most radical and vanguardist politics: Tiqqun, some aspects of Frankfurt School of Critical Theory
Best psychologists: C. G. Jung, L. Wittgenstein
most fun: Terence Mckenna