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There are 10 clues with the answer 'MIRTHLESS'
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CLUE
1.
Dull paper about Hitler's rewritten (9)
2.
Unhappy
3.
Solemn
4.
Sad
5.
Melancholy
6.
Gloomy
7.
Depressed
8.
Glum line adopted by Smithers surprisingly
9.
Shirt Mel's designed without Joy
10.
Unhappy with dress from behind - Henry not so much (9)