Catalytic enantioselective synthesis of small-molecule building blocks with allylic stereogenic centers is an important objective in organic synthesis, but preparing this motif wherein the adjacent olefin is 1,2-disubstituted in a single step is a tremendous challenge. Late-transition-metal-catalyzed intermolecular couplings of nucleophiles and 1,3-dienes in hydrofunctionalization reactions have quickly emerged as a compelling approach to these and related compounds. In this Perspective, we illustrate how these intermolecular diene hydrofunctionalizations have provided an avenue to complex, highly desirable chemical space that is not readily accessed by other technologies. We also aim to provide some insight into the varying mechanistic pathways and nuances of these myriad reactions to help inform future reaction and catalyst design.