In this paper we have not attempted to produce any kind of systematic review of simulation in healthcare to compete with the dozen (at least) excellent and comprehensive survey papers on this topic that already exist. We begin with a glance back at the early days of Wintersim, but then proceed, in line with the theme of this special track, to reflect on general developments in healthcare simulation over the years from our own personal perspectives. We include some memories and reflections by several pioneers in this area, both academics and healthcare practitioners, on both sides of the Atlantic. We also asked four current simulation modelers, who all specialize in healthcare applications but from very diverse perspectives, to reflect on their experiences. We endeavor to identify some common or recurring themes across the years, and end with a glimpse into the future.