The catalytic enantioselective hydrogenation of prochiral olefins is a key reaction in asymmetric synthesis. Its relevance applies to both industry and academia as an inherently direct and sustainable strategy to induce chirality. Here we briefly recount the early breakthroughs concerning the asymmetric hydrogenation of largely unfunctionalized olefins, from the first reports to the advent of chiral Crabtree-like catalysts. The mechanism and its implications on the enantioselectivity are shortly discussed. The main focus of this Perspective lies on the more recent advances in the field, such as the latest developed classes of ligands and the opportunity to employ more Earth-abundant metals. Therefore, separate sections consider iridium N,P-, NHC-, P,S-, and O,P catalysts, and rhodium, palladium, cobalt, and iron catalysts. Finally, the remaining unsolved challenges are examined, and the potential directions of forthcoming research are outlined.