The past can be used as a methodological perspective from which to view the dynamics of the anthroposphere and its interaction with Earth systems. The chapter offers for comparison two historical perspectives on societal collapse, the Mediterranean around 1200 BCE, and the fall of the Rome-based order around the Mediterranean, the Black Sea and Europe around 400 AD. We live in the first World system with a global horizon, meaning that there can be no direct historical precedents when talking about the contours of system-wide collapse. The chapter argues that some lessons can nevertheless be drawn from historical cases that did involve the breakdown (and eventual reconstitution) of a multi-civilisational world order. It concludes that collapses have a multicausal character. They sometimes take the form of a reversion to the previous incarnation of the system, and they come as surprises to those experiencing them, even when the multiple causes were obviously well known as the system reached the tipping point of collapse.