Singer with "Billboard" #1s in '74 and '99 (4)

I believe the answer is:

cher

(Other definitions for cher that I've seen before include "1987 Best Actress Oscar winner for "Moonstruck"" , "Singer; dear (French)" , "US singer/actress - French river/department" , "Moonstruck star" , "Sonny and - -" .)

I've seen this clue in the Newsday.

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