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Herein we investigate the influence of competing self-organizing phenomena on the hierarchical self-assembly of liquid crystalline brush block copolymers (LCBBCs). A library of LCBBCs are synthesized using ring-opening metathesis polymerization (ROMP) of norbornene side-chain functionalized monomers comprising (1) cholesteryl mesogen with nine methylene spacer and (2) semicrystalline poly(ethylene glycol) (PEG). The self-assembly of LCBBCs with variations in LC block content (7–80 wt %) are investigated in their melt state. All LCBBCs show two distinct thermal transitions corresponding to PEG semicrystalline phase and LC mesophases. Interestingly, the LCBBCs display a multilevel hierarchical structure evidenced by the results from X-ray scattering and transmission electron microscopy (TEM): (1) smectic A (SmA) mesophases (d = 3–7 nm) by the assembly of cholesteryl side chains and (2 …