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2 results for BOSSIEST from Modern Era puzzles:

Date	Grid	Clue	Author	Editor
Sat Feb 15, 2003	36D	Most overbearing	Rich Norris	Shortz
Mon Jan 20, 1997	8D	Most domineering	S. Spadaccini	Shortz

1 result for BOSSIEST from pre-Shortz puzzles:

Date	Grid	Clue	Author	Editor
Fri Dec 10, 1954	34D	Most dictatorial: Colloq.	Diana Sessions	Farrar

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