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Not familiar with Nilsson's music or can pretend to know a lot about him either but are you both suggesting that "Without you" isn't a great song? I'd never heard of him until I listened to a documentary on the radio about 10 years ago which explained his music even if he hadn't commited suicide as I had believed. Generally I feel that the likes of Tom Jones and Tony Christie represent the absolute nadir of popular music and would have tended to call their output "Cheesy" but whilst Nilsson may have been something of a two hit wonder, I still think "Without you" is actually a very good piece of song-writing.
Before I went out birdwatching this morning I sat at the piano and had a play around with the tune "Crazy Rhythm" and I was a bit surprised to see that the music was actually published in 1928 - about ten years earlier than i imagined. I was also curious to read reference to the prohibition in the lyrics and how this song started to very much define it's time. I suppose that the same can be said of Nilsson but when I looked him up on Wickipedia I was immediately reminded of Kurt Elling's last CD which consisted of material published from the Brill Building in the late sixties / early sixties. This is a fabulous record which uses the pop music of that period as a vehicle for some pretty interesting and very credible jazz. For me, the interesting fact is that there was a corps of extremely capable songwriters in the late 60's / early 70's(thinking of Carole King, etc) whose work easily stands up or even surpasses something like Wolfe Khan's "Crazy Rhythm." Granted that some of this music may have been generated for "manufactured" boy bands like The Monkees" but I thought most people know acknowledged that something like "Last train to Clarksville" was a pretty profound piece of music whereas the lyrics of a tune like "Pleasant Valley Sunday" are actually extremely knowing and cynical - check out Kurt Elling's re-harmonised version which is exceptional.
It's funny how the jazz audience reacts against certain types of performer or composition.
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