Answer: SADDEST

AnswerCrossword Clue
SADDESTMost pathetic.
saddestaffected by, marked by, or causing sorrow
saddestSAD, unhappy (sad)
SADDESTFarthest down?
SADDESTMost blue
SADDESTMost forlorn
SADDESTLower than the rest
SADDESTMost pathetic
SADDESTMost deplorable
SADDESTMost downcast
SADDESTMost dolorous
SADDESTMost morose
SADDESTWord for "It might have been!"
SADDESTMost miserable
SADDESTMost deplorable.
SADDESTMost pitiful
SADDEST"... the ... are these: 'It might have been!'": Whittier
SADDESTMost woeful
SADDESTBummed to the max
SADDESTMost down
SADDESTLeast cheerful
SADDESTMost mournful
SADDESTMost unhappy
SADDESTMost long-faced
SADDESTLeast happy
SADDESTLeast light-hearted
SADDESTSuperlatively sorrowful
SADDESTFurthest down in the dumps
SADDEST"The ... are these, 'It might have been'" (Whittier)