Supernovae arise from progenitor stars occupying the upper end of the initial mass function. Their extreme brightness allows individual massive stars to be detected at cosmic distances, lending supernovae great potential as tracers of the upper end of the IMF and its evolution. Exploiting this potential requires progress in many areas of supernova science. These include understanding the progenitor masses that produce various types of supernovae and accurately characterizing the supernova outburst and the environment in which it was produced. I present some preliminary work identifying the environmental conditions that produce the most luminous supernovae, believed to arise from stars with masses greater than 100 M_sun. I illustrate that the presence of these extreme supernovae in small star-forming dwarfs can be used to test our understanding of the upper end of the IMF.
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