Massive stars are nearly always found in close pairs when they are young. A very small fraction of these pairs stay together throughout their turbulent lives. They end their lives as a double black hole system. Their orbit slowly decays until, eventually, they coalesce. These mergers giving rise to such strong bursts of gravitational wave emission that they can be detected directly at earth. The gravitational wave detector LIGO has publicly announced two of such events at the time of writing as well as one candidate event. In this talk I will focus on the lives of the extreme progenitors of LIGO’s black holes and discuss what we are learning about the lives and deaths of the most massive stars.