COOLIO
| Date | Clue |
|---|---|
| 2023-03-11 | "Sweet!" |
| 2020-01-30 | "Gangsta's Paradise" rapper |
| 2018-11-02 | "Sweet" |
| 2017-04-30 | "Gangsta's Paradise" rapper |
| 2017-03-19 | "Gangsta's Paradise" rapper |
| 2012-12-07 | "1, 2, 3, 4 (Sumpin' New)" rapper |
| 2012-05-27 | "Gangsta's Paradise" rapper |
| 2010-12-08 | Rapper parodied by Weird Al Yankovic in "Amish Paradise" |
| 2003-01-09 | "Gangsta's Paradise" rapper |
| 2000-12-08 | "Too Hot" rapper |
| 2000-06-24 | Singer Artis Ivey, familiarly |
| 1997-02-09 | "Gangsta's Paradise" singer |