The observational study of supernovae is undergoing a revolution brought about by wide-field synoptic surveys. The abundance of data offers insights into one of the biggest mysteries in the field; what are the ultimate fates of high-mass stars? Recent work in the field has suggested a lack of SNe associated with the most massive stars. In this talk, I will present the PhD work that I have been leading into stripped-envelope (SE) supernovae (SNe), which are thought to have high-mass origins. First, I will present the first systematic search for SE SNe that are associated with the highest mass stars, which found a largely unexplored population of extremely high-mass SE SNe. Next, I will move on to a rare sub-type of circumstellar interacting SE SNe called Type Ibn. Whose origin could also be linked to extremely high-mass stars.