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There are 14 clues with the answer 'LEANNRIMES'
# CLUE
1.
Patsy Cline-like star with the breakout hit "Blue"
2.
US singer/songwriter and actress whose hit songs include How Do I Live, You Light Up My Life and Crazy (5,5)
3.
Winner of the 1997 Best New Artist Grammy (or homophonically, the starts of this puzzle's theme entries)
4.
Singer who is the youngest ever individual artist to win the Grammy: 2 wds.
5.
Country singer who achieved stardom at 13
6.
"Can't Fight the Moonlight" singer
7.
Singer whose "How Do I Live" spent 32 weeks in the Billboard Top 10 in 1997 and 1998: 2 wds.
8.
Singer with the 1997 3x platinum single "How Do I Live"
9.
"Something's Gotta Give" singer who goes by her middle name, not first name (Margaret): 2 wds.
10.
Singer Margaret ___
11.
Blue singer who performed in the 2002 Salt Lake City Winter Olympics opening ceremony: 2 wds.
12.
How Do I Live singer who won the fourth season of The Masked Singer as the Sun: 2 wds.
13.
"What I Cannot Change" singer
14.
First country singer to win the Best New Artist Grammy