COOLIO

Set to 5 different clues across 5 published puzzles, most often “Rapper parodied by Weird Al Yankovic in "Amish Paradise"” — The New York Times, Wednesday, 8 December 2010.

6 letters

Every clue on record, most used first

Rapper parodied by Weird Al Yankovic in "Amish Paradise"once
The New York Times — Wednesday, 8 December 2010
"Gangsta's Paradise" rapperonce
The New York Times — Thursday, 9 January 2003
"Too Hot" rapperonce
The New York Times — Friday, 8 December 2000
Singer Artis Ivey, familiarlyonce
The New York Times — Saturday, 24 June 2000
"Gangsta's Paradise" singeronce
The New York Times — Sunday, 9 February 1997