Almost since the beginning, massive stars and their resultant supernovae have played a crucial role in the Universe. These objects produce tremendous amounts of energy and new, heavy elements that enrich galaxies, encourage new stars to form and sculpt the shapes of galaxies we see today. The end of millions of years of massive star evolution and the beginning of hundreds or thousands of years of supernova evolution are separated by a matter of a few seconds, in which some of the most extreme physics found in the Universe causes the explosive and terminal disruption of the star. Key questions remain unanswered in both the studies of how massive stars evolve and the behaviour of supernovae, and it appears the solutions may not lie on just one side of the explosion or the other or in just the domain of the stellar evolution or the supernova astrophysics communities. The need to view massive star evolution and supernovae as continuous phases in a single narrative motivated the Theo Murphy international scientific meeting Bridging the gap: from massive stars to supernovae at Chicheley Hall in June 2016, with the specific purpose to simultaneously address the scientific connections between theoretical and observational studies of massive stars and their supernovae, through engaging astronomers from both communities.