Messier 5: 27,000 Light Years
If any of the few Neanderthals that were still alive 27,000 years ago saw M5, it was as a dim fuzzy star. A mile-thick sheet of ice still covered northern Europe and much of North America. While fur coats were definitely the fashion, here's a BBC news story about woven cloth possibly dating back this far.
The cave painting is from Lascaux, and is dated to right around that time.