This is the first textbook treatment of work leading to the landmark 1979 Kazhdan-Lusztig Conjecture on characters of simple highest weight modules for a semisimple Lie algebra $mathfrak{{g}}$ over $mathbb {{C}}$. The setting is the module category $mathscr {{O}}$ introduced by Bernstein-Gelfand-Gelfand, which includes all highest weight modules for $mathfrak{{g}}$ such as Verma modules and finite dimensional simple modules. Analogues of this category have become influential in many areas of representation theory. Part I can be used as a text for independent study or for a mid-level one semester graduate course; it includes exercises and examples. The main prerequisite is familiarity with the structure theory of $mathfrak{{g}}$. Basic techniques in category $mathscr {{O}}$ such as BGG Reciprocity and Jantzen's translation functors are developed, culminating in an overview of the proof of the Kazhdan-Lusztig Conjecture (due to Beilinson-Bernstein and Brylinski-Kashiwara). The full proof however is beyond the scope of this book, requiring deep geometric methods: $D$-modules and perverse sheaves on the flag variety. Part II introduces closely related topics important in current research: parabolic category $mathscr {{O}}$, projective functors, tilting modules, twisting and completion functors, and Koszul duality theorem of Beilinson-Ginzburg-Soergel.