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There are 14 clues with the answer 'LOSIN'
# CLUE
1.
David Archuleta song "___ Sleep"
2.
Heads off when nearer to the winner, but not near enough (5)
3.
"___ Control" (2015 Russ song)
4.
Winnin' opposite
5.
"___ It" (1983 Cruise movie)
6.
"___ It" (1983 Tom Cruise movie)
7.
'I Can't Win for ___ You' (1986 country hit)
8.
"__ It": 1983 Tom Cruise film
9.
Lynyrd Skynyrd's "Am I ___"
10.
1983 Tom Cruise film, ___ It
11.
"___ It": Tom Cruise film
12.
"___ It" (1983 Tom Cruise film)
13.
Tom Cruise-Shelley Long film, ___ It
14.
1986 country tune by Earl Thomas Conley: "I Can't Win for ___' You"