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CHART ATTACK!: 11/20/76
I tried with Rufus...I REALLY tried, but I couldn't warm up to his songs.
Too bad you don't appreciate Rufus Wainwright (have you heard his recreation of the famous Judy Garland at Carnegie Hall concert?), but the McGarrigles and Loudon III have had a smaller following, I think, and certainly in recent years.
Cissy Houston was a hell of a gospel singer (can you say that about gospel singers?) before Whitney came on the scene. Tim Buckley got an influx of new listeners when people fell in love with Jeff's voice (even before his far-too-early death). Rapper Nas's dad is jazz trumpeter Olu Dara, who has quite a following in that realm but not much outside it.
There must be more. Just a thought.