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Sinatra. He slipped from speech to song without stopping to arrange himself into the posture of a singer. That's how he made songs make sense. He was the best at that. As far as hanging out, there is no one I would rather hang out with than Sinatra, especially during the rat pack days.
Almost went with Jimi Hendrix, but my instinct told me to choose Nirvana... since I was in high school from 1990-94, they were the music of my generation! If I could choose more specifically, though, I'd want to attend their Unplugged (MTV) concert. One of the best sets/albums ever, imo.
Of this list I would like to see The Beatles, Michael Jackson at his prime and maybe Sinatra for his legendary status, but I have to choose Nirvana here because their run was the shortest. One of my favorite concert experiences is actually seeing a Nirvana cover band that used to play here, and it was always a good time.
I saw Hendrix and the Doors in 1968 and once was enough for each (while the Hendrix show was excellent, the Doors just phoned theirs' in). I saw Sinatra in the mid-1970s and am sorry I never saw him again. My mother saw him in 1944-45 and her description of the event was bigger than most Beatles' shows. I know a couple of folks who saw the Beatles in the mid-1960s and while they were thrilled with seeing them they couldn't enjoy the performance because the couldn't hear much of it. I never saw Marvin Gaye and would have enjoyed it and I would have liked to see the Stones in their prime or their impromptu performance with Muddy Waters (which is on video).
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