| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| 2012: "Luck or Something Like It" by a singing "gambler" | Kenny Rogers | $1,200 | DJ | MUSICIANS' AUTOBIOGRAPHIES | 2013-06-17 | #6631 | |
| This "Gambler" took a chance & recently published a book of his photos of America | Kenny Rogers | $100 | J | MUSIC PEOPLE | 1987-09-18 | #695 | |
| Once a member of the New Christy Minstrels, this "Gambler" later became a top C&W artist | Kenny Rogers | $200 | DJ | FOLK MUSIC | 1985-09-24 | #272 |