Previous studies of the relation between insider ownership and dividend policy have focused only on U.S. or European firms from a legal system perspective. We explore how the effects of the increase in insider ownership concentration on the dividend policy change in different legal, corporate governance, and cultural environments in Asian countries. The severity of agency problems between controlling insiders and outside investors in Asian countries provides a unique circumstance for exploring this issue. We find that insider ownership has an inverse U-shaped relation with dividend payouts in Asian countries and that the inversely U-shaped relation becomes stronger in common law, strong corporate governance, low long-term orientation, or low uncertainty avoidance countries.