It's actually quite funny.
The people who are Japanese but are not absorbed in current Japanese culture (Japanese-born International Citizens, 2nd Generation Japanese, etc.) are more likely to know about Shiina, BUT
the people who's "hobby" it is to know as much about modern Japanese pop culture as possible (so-called "Japanophiles") generally don't know about Shiina because they're too busy with the pop idols.
Just my two cents. Nobody in my class knew who Shiina Ringo was except for the teacher.
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