| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| This "Gambler" recently hit the jackpot with "Buy Me A Rose", his first chart-topper in 13 years | Kenny Rogers | $600 | DJ | COUNTRY STARS | 2001-04-10 | #3832 | |
| Sheena Easton made it to the country charts when she did the duet "We've Got Tonight" with this man | Kenny Rogers | $500 | J | A LITTLE BIT COUNTRY | 1998-05-22 | #3175 |