An unprecedented magnitude of land-use/land-cover changes have led to a rapid conversion of tropical forested landscapes to different land-uses. This comparative study evaluates and reconstructs the recent history (1976–2019) of land-use change and the associated land-use types that have emerged over time in two neighboring rural villages in Southern Mexico. Qualitative ethnographic and oral histories research and quantitative land-use change analysis using remote sensing were used. Findings indicate that several interacting historical social-ecological drivers (e.g., colonization program, soil quality, land conflicts with indigenous people, land-tenure, availability of surrounding land where to expand, Guatemala’s civil war, several agricultural development and conservation programs, regional wildfire, Zapatista uprising, and highway construction) have influenced each village’s own unique land-use change history and landscape composition: the smaller village is characterized by a dominating pasture landscape with some scattered agricultural and forest areas, while the larger village has large conserved forest areas intermixed with pastures, agriculture, oil palm and rubber plantations. The differential histories of each village have also had livelihood diversification implications. It is suggested that landscape history research in tropical agroforest frontiers is necessary because it can inform land-use policies and forest conservation strategies that are compatible with local livelihoods and conservation goals.