Three different omega-alpha-substituted styryl macromonomers with well-controlled structures were synthesized by directly terminating either polystyryllithium or polyisoprenyllithium with 4-(3-halopropyl)-alpha-methylstyrenes (2), alpha-(3-halopropyl)styrenes (3), and 1-[4-(3-halopropyl)phenyl]-1-phenylethylenes (4). With uses of their bromo and iodo derivatives as terminating agents, the reactions proceeded in a desired manner in THF at -78 degrees C to afford well-controlled omega-styryl polystyrene and polyisoprene macromonomers quantitatively. On the other hand, the synthetic utility of chloride derivatives as terminators was much dependent-on both their polymerizable styryl groups and living polymers to be reacted. By comparison of these results with our previous results using 4-(3-halopropyl)styrenes (1), the scope and limitation of the methodology developed here were discussed from a viewpoint of quantitative synthesis of various omega-styryl macromonomers with well-controlled structures.