Phillip Tobias once dated the earliest Bushmen to about 40,000 years ago, though recent findings at several sites trace the origin of symbolic culture in southern Africa to more than twice that figure. What this means in terms of either the origins of language or the relation between the earliest symbolism and living populations is, of course, open to debate. A clear solution to such a debate would also dissolve any difference between what in southern Africa are known as the Middle Stone Age and the Later Stone Age. Archaeological findings such as those of early rock art give a better clue to Bushman prehistory. These can be dated to at least 25,500 BCE, although again the connection with people called ‘Bushmen’ today is far from certain. This chapter will explore these and other issues, as well outline the discoveries of contemporary archaeology. The latter include Iron Age migrations into Bushman territories and possible connections with hunter-gatherer groups in eastern Africa.