16.3-15.5 million years ago
Teeth are tough, and survive better than most bones. We can recognize apes by their teeth: ape and human molars have 5 cusps that form a distinctive Y pattern. Early Miocene apes like Proconsul already had this pattern. They had also already lost their tails. But in other respects they were more like monkeys than living great apes. They walked on their palms like monkeys, meaning they mostly walked on top of branches, instead of hanging underneath them.
How we get to modern great apes is somewhat mysterious. Apes may have left Africa for Europe and Asia as early as 16 million years ago, or maybe more like 14 Mya. A variety of great apes develop in Asia, although orangutans are now the only survivors. But we’re not sure whether the ancestors of African great apes are apes that stayed in Africa, or whether they’re apes that developed more modern features in Eurasia and then migrated back to Africa.
The various genera of great apes all make some kind of compromise between walking and hanging from branches. When orangutans are on the ground (which is not very often), they walk on the edges of their hands. Chimpanzees and gorillas walk on the knuckles of their hands. And of course humans walk on their hind legs. These are all pretty unusual ways to get around.
It would be nice to know whether human ancestors went through a knuckle walking phase. African fossils are skimpy for this period, and likely to remain so. Maybe genetics will have something to tell us about whether chimp ancestors took to knuckle walking before or after they spit from human ancestors.