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There are 5 clues with the answer 'PUSHINGTIN'
# CLUE
1.
1999 comedy-drama film starring John Cusack and Bill Bob Thornton (7,3)
2.
1999 comedy drama starring Angelina Jolie which is based around the real world radar facility New York TRACON: 2 wds.
3.
1999 comedy-drama film starring John Cusack and Billy Bob Thornton (7,3)
4.
1999 comedy-drama film starring John Cusack and Billy Bob Thornton
5.
1999 film about air traffic controllers, and a hint to this puzzle's theme