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There are 9 clues with the answer 'WAYLON'
# CLUE
1.
Singer Jennings
2.
Jennings of country
3.
Mr Burns' assistant in The Simpsons, ------ Smithers (6)
4.
-- Jennings, 1937-2002, country singer-songwriter (6)
5.
Mr Burns' assistant in The Simpsons, ... Smithers (6)
6.
Jennings of country music
7.
Country's Jennings
8.
Country singer Jennings
9.
Burns' assistant easily nails two rhymes (6,8)