Understanding Massive Star Evolution Phil Massey Lowell Observatory Massive stars are rare: we expect that for every star with a mass 20 times that of the sun, there are a hundred thousand solar-type stars in the Galaxy; for every star with a mass 100 times that of the sun, there are over a million. Nevertheless, these scant heavyweights provide most of the energy input and chemical enrichment of the interstellar medium. The physics of massive stars is complicated by strong stellar winds (mass-loss) and convective overshooting, making reliable stellar evolution models difficult to construct. I will describe the current state of our understanding of massive star evolution, emphasizing recent observational tests using young clusters in the Milky Way and Magellanic Clouds. These studies provide the first empirical measurement of the progenitor masses of various types of evolved massive stars, such as Wolf-Rayet stars, Luminous Blue Variables, and red supergiants. The results demonstrate the significant effect that metallicity has on the evolution of massive stars.