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There are 27 clues with the answer 'HIGHHOPES'
#
CLUE
1.
Drunken optimism? (4,5)
2.
1988 Mike Leigh comedy-drama film starring Phil Davis and Ruth Sheen (4,5)
3.
1988 Mike Leigh comedy-drama film starring Phil Davis and Ruth Sheen
4.
Humming old star's song (4,5)
5.
Has ambitions to be on drugs?
6.
*What an idealistic person has
7.
1-Across hit
8.
Optimist's hallmark
9.
1959 Best Original Song Oscar winner
10.
Optimistic feelings
11.
Sinatra tune used as JFK's campaign song
12.
Sinatra standard with "Oops there goes another rubber tree plant"
13.
Sinatra standard
14.
Oscar-winning song from "A Hole in the Head"
15.
Oscar-winning song Sinatra used to campaign for JFK
16.
Optimistic expectations
17.
Optimism
18.
Great expectations
19.
Expectation
20.
Anticipation
21.
1959's Best Song Oscar winner
22.
1959 Academy Award-winner from "A Hole in the Head"
23.
1959 Academy Award song
24.
A version of this Frank Sinatra song was used in John F. Kennedy's 1960 presidential campaign (4,5)
25.
1988 Mike Leigh film starring Philip Davis and Ruth Sheen (4,5)
26.
Frank Sinatra song including the line: “There goes another rubber tree plant”
27.
Mountaineer's great ambitions (4,5)