Massive stars play a major role in the evolution of their host galaxies and serve as important probes of the distant Universe. It has been established that the majority of massive stars reside in close binaries and interact with their companion stars during their lifetimes. Such interactions drastically alter their life cycles and complicate our understanding of their evolution, but are also responsible for the production of interesting and exotic interaction products. Within my research group we aim to push forward the theory of massive star evolution through large scale simulations of stellar evolution, providing connections to both electromagnetic and gravitational wave observations.