| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| Robert Van Winkle is the real name of this rapper who was "cool" in the early 1990s | Vanilla Ice | $600 | J | MUSIC MISCELLANEA | 2024-11-12 | #9202 | |
| 1991: "Ice by Ice" | Vanilla Ice | $800 | DJ | MUSICIANS' AUTOBIOGRAPHIES | 2013-06-17 | #6631 | |
| With 1998's "Hard to Swallow" this white guy from Miami tried to recapture his gangster rap success | Vanilla Ice | $800 | DJ | H2O MUSIC | 2008-03-19 | #5423 |