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There are 3 clues with the answer 'ALISONKRAUSS'
# CLUE
1.
Singer who won her 27th Grammy for the 2011 bluegrass album "Paper Airplane": 2 wds.
2.
When You Say Nothing at All country singer who has won 27 Grammys: 2 wds.
3.
When You Say Nothing At All singer who collaborated with Brad Paisley on the 2004 country hit Whiskey Lullaby: 2 wds.