Understanding the extinction of Australopithecus and origins of Paranthropus and Homo in South Africa has been hampered by the perceived complex geological context of hominin fossils, poor chronological resolution, and a lack of well-preserved early Homo specimens. We describe, date, and contextualize the discovery of two hominin crania from Drimolen Main Quarry in South Africa. At similar to 2.04 million to 1.95 million years old, DNH 152 represents the earliest definitive occurrence of Paranthropus robustus, and DNH 134 represents the earliest occurrence of a cranium with clear affinities to Homo erectus. These crania also show that Homo, Paranthropus, and Australopithecus were contemporaneous at similar to 2 million years ago. This high taxonomic diversity is also reflected in non-hominin species and provides evidence of endemic evolution and dispersal during a period of climatic variability.