| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| "There's a Tear in My Beer" was a 1989 duet hit by this man & his father who had died 36 years earlier | Hank Williams, Jr. | $600 | DJ | COUNTRY MUSIC STARS | 1999-03-19 | #3355 | |
| This famous "Junior" called one of his early backup bands The Cheatin' Hearts | Hank Williams, Jr. | $600 | DJ | COUNTRY SINGERS | 1998-01-12 | #3081 | |
| "All My Rowdy Friends Are Comin' Over Tonight" won him the first CMA award for Music Video of the Year | Hank Williams, Jr. | $500 | J | COUNTRY SINGERS | 1997-06-18 | #2963 |