The ongoing LIGO/VIRGO gravitational-wave detections sparked an international “hunt†for stellar-mass black holes in our own Cosmic neighborhood. Of special interest are black hole components in massive binaries (OB+BH). These systems offer key probes linking between their speculated progenitors – Wolf Rayet binaries – and their possible descendants: black hole mergers. Thousands of OB+BH binaries are expected to reside in the Milky Way and the Magellanic Clouds. However, only few are known, usually appearing as X-ray binaries. Multiple reports of OB+BH systems have emerged in the last years, but almost all have been refuted by following studies. Finding such systems will yield precious constraints on core-collapse physics and binary interaction at the upper-mass end. I will start the talk by discussing recent insights on the putative progenitors of black holes: Wolf-Rayet stars, including some open problems regarding their formation. I will continue by highlighting refuted black hole detections, and show how these led to the discovery of a new type of post-interaction binary systems. Finally, I will conclude with current ongoing efforts to find quiescent OB+BH systems using Gaia and spectroscopic techniques, including a few promising candidates.