The notion of legalizing any sort of illicit drug seemed preposterous to most people just twenty years ago. Now cannabis is being legalized in a growing number of states and countries, psychedelic legalization is proceeding much faster than anyone expected, and in Colombia the president and other leading political figures are talking openly of legalizing cocaine. There are, of course, many ways to legally regulate previously illegal psychoactive drugs. Perhaps no one is more expert on these issues than Steve Rolles at the UK-based Transform Drug Policy Foundation. We talked and debated about various models of legally regulating cannabis, psychedelics and stimulants; the evolving role of the US government and UN agencies; and current developments in Europe, the Americas and Asia.