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There are 14 clues with the answer 'PRINE'
# CLUE
1.
John with four Grammys and a Lifetime Achievement Grammy
2.
John who sings "Angel From Montgomery"
3.
"Common Sense" John
4.
Folksinger John
5.
Country/folkster John
6.
Dylanesque singer
7.
John of "Dear Abby"
8.
Folk-rock singer John
9.
Folk songwriter John
10.
Folk singer John
11.
"Angel From Montgomery" singer John
12.
John who received a Grammy Lifetime Achievement Award in 2020
13.
Folksy singer John of "Dear Abby"
14.
Folk singer John whose last name rhymes with a number