GLOAT

Set to 7 different clues across 12 published puzzles, most often “Be a bad winner” — The New York Times, Friday, 9 March 2007.

5 letters

Every clue on record, most used first

Be a bad winner6 times
The New York Times — Friday, 9 March 2007
Show snide satisfactiononce
The New York Times — Tuesday, 18 July 2000
Exhibit annoying satisfactiononce
The New York Times — Tuesday, 8 September 1998
Say "I told you so!"once
The New York Times — Friday, 19 January 1996
Show smugnessonce
The New York Times — Sunday, 25 September 1994
Show impolite satisfactiononce
The New York Times — Saturday, 4 December 1993
Crowonce
The New York Times — Sunday, 28 November 1993