Artificial Intelligence and Rule of Law are shaping up to be inversely correlated. Artificial Intelligence will inevitably stifle vested fundamental rights that we, collectively, hold so dear. The unbridled rise of Artificial Intelligence will accordingly fray the fabric of Rule of Law, which is already backsliding in some parts of the world. With this context in place, this long-winded chapter parses my newly-crafted concept of Algorithmic Dictatorship that arises out of discriminatory algorithmic decision-making undertaken by Artificial Intelligence that affects the fundamental rights of citizens devoid of, and fundamentally decoupled of, any reasonable grounds to do so. Pivotally, algorithmic life-changing decisions (those pertaining to citizens’ health, wealth, freedom, and credit scoring) should be subject to stringent scrutiny or inordinate damages may otherwise occur. This is the kernel of «inequality in application» that consists of Artificial Intelligence-embedded technologies that seemingly works well for everyone, when such is not the case. The paradigmatic examples of errors-fraught evaluations undertaken by machine learning algorithms are legion. This chapter brings them into a sharper focus.