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I think of 'oldies' as Ragtime leading up to the 1920's/30's. My favourite song for enjoyable pop ditties (off the top of my head) would skip the 1960's and 70's entirely and very likely be "Mr Five by Five" from the 30's or 40's; not sure exactly when that written without checking.
For the more serious music, I would go with I Know Why (and so do you) and When Angels sing. The version of I know Why as sung by Paula Kelly with the Glenn Miller orchestra would likely place on my overall top ten list of songs.
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Started talking to yourself I see.
Yes, it's the only way I can be certain of an intelligent conversation.
Black Adder
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