The recent generation of dedicated wide-field, high-cadence sky-surveys have overwhelmed discovery statistics for all manner of extra-galactic transients, and uncovered new phenomena seemingly linked to the demise of massive stars. For the more established classes of transients, such as core-collapse supernovae, surges in discoveries are allowing true population studies to provide quantitative constraints not only on the explosion properties, but also on the progenitor populations. Crucially, such population insights are benefiting from creation of samples of transients constructed with largely unbiased methods for discovery and characterisation. Surrounding these discoveries are increasing samples of extreme transients that do not fit the standard core-collapse paradigm - requiring the invocation of exotic progenitor stars and placing demands on the stellar evolution of such systems. Here I will provide a high-level observationally-driven overview of recent results related to massive stellar transients.