Billboard Hits With A Question Mark

Can you name the artists with multiple Billboard Hot 100 hits ending in a question mark, and the names of those songs?

Classic Type in answers that appear in a list
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YearAnswer
ARTIST (place name)
1990
1987
1971
ARTIST (girl group)
1965
1964
ARTIST (canadian singer)
1995
1992
ARTIST (male synth artist)
1986
1984
ARTIST (male 50's singer)
1957
1957
YearAnswer
ARTIST (R&B offshoot of other band)
1991
1990
ARTIST (lead singer A.L.)
1985
1984
ARTIST (American Idol judge)
2002
1999
ARTIST (renamed from Catch 22)
1991
1988
ARTIST (R&B male)
1994
1992

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