| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| In 1942 this crooner had a No. 1 hit with "White Christmas" | Bing Crosby | $200 | J | OTHER CHRISTMAS SONGS | 2015-12-22 | #7197 | |
| This crooner's "Sweet Leilani" from the 1937 film "Waikiki Wedding" won an Oscar for best song | Bing Crosby | $200 | J | SWEET SONGS | 1996-12-31 | #2842 | |
| Crooner who sang "Sweet Leilani" in "Waikiki Wedding" | Bing Crosby | $600 | DJ | OSCAR SONGS | 1985-01-09 | #88 |