| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| His 1966 No. 1 hit "Strangers In The Night" was released on his own Reprise Records label | Frank Sinatra | $400 | DJ | POP MUSIC | 1997-07-15 | #2982 | |
| In 1966, he had 4 Top 40 hits including "It Was A Very Good Year" | Frank Sinatra | $100 | J | POP MUSIC | 1990-09-10 | #1381 | |
| Title tune of his new album, "L.A. Is My Lady" is contender for that city's song | Frank Sinatra | $300 | J | POP MUSIC | 1985-04-02 | #147 |