Filed from 4 published puzzles

ITSASHAME

Set to 4 different clues across 4 published puzzles, most often "Alas" — The New York Times, Saturday, 24 April 2010.

9 letters

Every clue on record, most used first

"Alas"once
The New York Times — Saturday, 24 April 2010
"Something really should be done"once
The New York Times — Saturday, 23 April 2005
"Terrible pity"once
The New York Times — Saturday, 1 November 2003
Waistband that's tucked in -- pity, that!?once
The New York Times — Sunday, 30 April 2000

Other answers to these clues

AHME4 letters
DEARME6 letters
IFEAR5 letters
OHME4 letters
SADLY5 letters
SADTOSAY8 letters
SOSAD5 letters
TOOBAD6 letters
WOEISME7 letters