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There are 37 clues with the answer 'DREARIEST'
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CLUE
1.
Most boring drunk I arrested (9)
2.
Dullest back in engraving stamp on the way
3.
Barking Advertiser sacking five is most sad (9)
4.
Criminal I arrested is most sad (9)
5.
Stop holding back, saint is most dull
6.
Doctor finds cultivating a tree is most dull
7.
Extremely dull criminal I arrested
8.
Desert air (anag) (9)
9.
Most bleak
10.
Desert air (anag)(9)
11.
The most doleful is the most wearisome
12.
Most gloomy (9)
13.
Most depressing listener is also among the most uninteresting (9)
14.
Most drab or depressing (9)
15.
Maximally cheerless
16.
Most tiresome ducks crossing river close to boat
17.
Most morbid
18.
Its reader turned out to be most dull (9)
19.
Fitful rise in foreign trade is most depressing (9)
20.
Dullest listener interrupts with fewest tears (9)
21.
Doctor finds irregular eater is most dull
22.
Most gloomy
23.
Least rosy
24.
Twilit
25.
Most dismal
26.
Least sunny
27.
Least pleasant, weatherwise
28.
Gloomiest
29.
Dullest
30.
Pass street entertaining hindmost, suggesting it's most drab and depressing