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This paper outlines the major judicial decisions and legislative initiatives that have shaped the growth of various types of maternity and parental leave employment benefits in the United States and Canada and analyzes the differences and similarities in the United States and Canadian evolution of these benefits. It presents the major judicial arguments in detail, because these arguments represent social and economic perspectives that shaped the labor market opportunities afforded women in the United States and Canada throughout the beginning and the middle of this century. It also highlights the interaction between judicial decisions and legislative initiatives in influencing the availability of leave.