WOES

Set to 19 different clues across 24 published puzzles, most often “Troubles” — The New York Times, Sunday, 16 November 2003.

4 letters

Every clue on record, most used first

Troubles4 times
The New York Times — Sunday, 16 November 2003
Bounced checks, hangnails, etc.2 times
The New York Times — Friday, 3 November 2006
Trials2 times
The New York Times — Sunday, 21 May 2006
Headachesonce
The New York Times — Sunday, 29 May 2011
Reasons to cryonce
The New York Times — Sunday, 11 April 2010
Sorrowsonce
The New York Times — Wednesday, 28 October 2009
Things to worry aboutonce
The New York Times — Friday, 21 November 2008
Depression causesonce
The New York Times — Sunday, 1 June 2008
Tribulationsonce
The New York Times — Tuesday, 9 October 2007
Melancholiac's listonce
The New York Times — Thursday, 5 April 2007
Griper's litanyonce
The New York Times — Friday, 17 March 2006
Tormentsonce
The New York Times — Sunday, 12 June 2005