Frank Sinatra is that big?

In college I had a summer job on Wall Street in which I did nothing much. One day my supervisor assigned me a peculiar task. I was asked to wake up early and stand in line outside Carnegie Hall to buy tickets for a series of Frank Sinatra concerts. At 20, I was dumbfounded by the request. Get up how early? Was this really necessary for Frank Sinatra? Being low intern on the totem pole, I did as requested. Despite arriving at 5:00am, the mission was a complete bust. Shockingly, I wasn't even able to get in line. The line was closed, the blocks surrounding Carnegie Hall were stuffed with middle-aged people (or their interns), the tickets were nearly sold out.

What is the psychological import of this anecdote? The recent death of many rock 'n roll icons, like Prince and David Bowie, has been surprisingly disturbing to me. Yet, I can see younger people react with indifference or at most, low level appreciation. I recognize their reaction as one I felt 35 years ago "is Prince really such a big deal?"