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Wow Craig, your 2nd clue was no help for me, then you mention "calypso is close" --and Belafonte was the first person I thought of yesterday, but could not find any song that charted low that matched the melody, and his stats were almost the same: one top ten (Day-o aka Banana Boat Song) but 7 USA top ten, not 8, and no peak at #66 on the chart I'm looking at, but 7 is so close and Belafonte is so Calypso that I feel the need to go examine closer his singles that charted low in the hopes that you were quoting different charts than I was looking at.

Once I've eliminated Harry Belafonte, though, I'm back at square zero...ugh...

Hmm. I was thinking after posting the number of top 40 songs was 8 for this artist I thought it was wrong. When I was finally able to look at Billboard this artist had 7 top 40 songs - but it’s not Belafonte! The Calypso is just a general reference, though the artist’s songs would fit a sub-tropical/tropical theme. The artist who sang and co-wrote the mystery tune was a writer for Billboard Magazine around the late ‘60s.