TUPAC

Set to 5 different clues across 8 published puzzles, most often “Rapper ___ Shakur” — The New York Times, Tuesday, 6 April 2010.

5 letters

Every clue on record, most used first

Rapper ___ Shakur3 times
The New York Times — Tuesday, 6 April 2010
First name in rap2 times
The New York Times — Friday, 12 March 2010
Rapper with the 1996 nine-time platinum album "All Eyez on Me"once
The New York Times — Sunday, 17 August 2008
Rapper Shakuronce
The New York Times — Tuesday, 5 June 2007
Late name in raponce
The New York Times — Sunday, 1 January 2006