Today would be Frank Sinatra's 100th birthday if he was still alive - and it's interesting how reactions to Sinatra define one's age. When I was a teenager, growing up on the Beatles, Rolling Stones and Bob Dylan, Sinatra was the epitome of unhipness (though 20 years earlier he had been the very epitome of hipness). A liking for Frank's records then would have guaranteed the ridicule of one's classmates - though plenty of older people were still buying them. Yet over time I came to appreciate his art and enjoy his recordings - or at least his earlier ones.
I think part of the problem was that in his later years, Frank tried too hard to keep up with the changing times. This led him to record material - like Hey Jude, and probably Paul Simon's worst song, Mrs Robinson - that were simply not right for his voice and style. The result was somewhat embarrassing, like seeing one's grandmother twerking. But within his own comfort zone, Sinatra was unmatchable. No one making the transition from youth to middle age can fail to be moved by the album September of My Years, Sinatra's meditative musical reflections on turning 50.
I will have more to say about music another time, but for now, let me just echo Bob's words: "Happy Birthday, Mr Frank". And if you want to deliver that message musically, you may be interested to learn that the ubiquitous song Happy Birthday to You is finally out of copyright.