Significance Isolated and infrequently colonized, islands harbor many of nature’s most renowned evolutionary radiations. Despite this evolutionary exuberance, island occupation has long been considered irreversible: The much tougher competitive and predatory milieu on mainlands prevents colonization, much less evolutionary diversification, from islands to continents. To test these postulates, we examined neotropical Anolis lizards, asking what happens when mainland and island evolutionary radiations collide. Far from being a dead end, we show that island-to-mainland colonization seeded an extensive radiation that achieved its ecomorphological disparity in ways distinct from their island ancestors. Moreover, when the incumbent and island-derived radiations collided, the ensuing interactions favored the latter, together highlighting a persistent role of both historical contingency and determinism in adaptive radiation.