CURLIEST

Set to 2 different clues across 2 published puzzles, most often “Maximally kinky” — The New York Times, Saturday, 23 October 2010.

8 letters

Every clue on record, most used first

Maximally kinkyonce
The New York Times — Saturday, 23 October 2010
Like Larry of the Three Stooges, surprisinglyonce
The New York Times — Sunday, 13 August 2006