| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| His 1964 hit "Oh, Pretty Woman" received a Grammy nomination, but lost; a 1990 remake won him a Grammy | Roy Orbison | $200 | J | HAIL, HAIL, ROCK 'N' ROLL | 2002-04-23 | #4072 | |
| He co-wrote "Only the Lonely" & offered it to Elvis before recording it himself | Roy Orbison | $200 | J | ROCK 'N' POP | 2000-04-24 | #3611 |