Find some music from the 1940’s on YouTube and let him watch that for an hour or so. If there is any that is. Then find some 1950’s Elvis and let him watch that. There’s some good examples of live Elvis performances from the 1950’s on YouTube. And lots from the 70’s but they are perhaps best avoided.
For non-musical comparisons I think Bill Gates and Steve Jobs as the superstars of a new culture of technology.