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Answer:
COOLIO
Possible Questions:
"Gangsta's Paradise" rapper
Rap star
'Gangsta's Paradise' rapper
Singer Artis Ivey, familiarly
Rapper with the album ''Gangsta's Paradise''
Rapper parodied by Weird Al Yankovic in "Amish Paradise"
Rapper Artis Ivey, familiarly
"Too Hot" rapper
"It Takes a Thief" rapper
"Gangsta's Paradise" singer
"Gangsta's Paradise" rapper who converted to Juggalo
"Gangsta's Paradise" Grammy winner
"1, 2, 3, 4 (Sumpin' New)" rapper
''Gangsta's Paradise'' Grammy winner