After decades of preparation, the era of gravitational wave astronomy has begun. The gravitational wave detectors, LIGO and Virgo, have published a catalog of 50 events of coalescing compact objects including black holes and neutron stars. I will discuss the role that numerical relativity played in the unveiling of the gravitational wave sky and anticipate how it might improve our understanding of gravity as the detectors improve. Throughout, I will attempt to highlight open questions and computational and data challenges.