Answer:

saddest

Answer	Crossword Clue
SADDEST	Most pitiful
SADDEST	"The ... are these, 'It might have been'" (Whittier)
SADDEST	Furthest down in the dumps

SADDEST	Superlatively sorrowful
SADDEST	Least light-hearted
SADDEST	Least happy
SADDEST	Most long-faced
SADDEST	Most unhappy
SADDEST	Most mournful
SADDEST	Least cheerful
SADDEST	Most down

SADDEST	Bummed to the max
SADDEST	Most woeful
SADDEST	"... the ... are these: 'It might have been!'": Whittier
SADDEST	Most pathetic.
SADDEST	Most deplorable.
SADDEST	Most miserable
SADDEST	Word for "It might have been!"
SADDEST	Most morose

SADDEST	Most dolorous
SADDEST	Most downcast
SADDEST	Most deplorable
SADDEST	Most pathetic
SADDEST	Lower than the rest
SADDEST	Most forlorn
SADDEST	Most blue
SADDEST	Farthest down?