History, culture, polity, and economy in Southeast Asia are diverse. Owing to pre-colonial, colonial and post-colonial histories of most nations in the region like the Philippines and Malaysia, their labour laws exhibit pluralism, having exogenous (civil law, common law) and endogenous (indigenous, customary rules) elements. The evolution of such laws over time and in specific contexts influenced varieties of capitalism and labour markets. This paper gives a cross-case theme analysis of how labour laws and work evolved in post-colonial Philippines and Malaysia within the wider, shifting milieu of Southeast Asia. The themes – developed from the bottom-up through an inductive analysis of historical data – provide depth and breadth to the latter and help explain tensions within these societies. Work informality, Spanish-American antecedents, import substitution industrialisation, export oriented industrialisation and exported labour policy are some major themes in the Philippines. In Malaysia, state regulation through labour rights, “sporadic” and “peripheral” role of common law, work creation and ethnicity are among key themes. These suggest that in Southeast Asia legal/economic pluralism and unemployment/underemployment are associated. Endogenous labour law changes are among important stimuli to labour market and work construction. Where such vital changes are wanting, work/employment and its quality are lacking.