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There are 6 clues with the answer 'TOBYKEITH'
# CLUE
1.
"Made in America" country singer who owns racehorses: 2 wds.
2.
"Red Solo Cup" singer who goes by his first and middle names, not his last name (Covel): 2 wds.
3.
Singer who duetted with Willie Nelson on the 2003 hit
4.
This recently deceased country star went by his first and middle names, dropping his surname Covel
5.
Red Solo Cup singer whose songs have spent 53 weeks at #1 on Billboard's Hot Country chart: 2 wds.
6.
Country singer with the 2014 song Drunk Americans: 2 wds.