| Date | Grid | Clue | Author | Editor |
|---|---|---|---|---|
| Sun, Jun 18, 2023 | 3D | Crooner in the Canadian Music Hall of Fame | Joe DiPietro | Shortz |
| Fri, Jul 22, 2011 | 38A | Co-writer of Michael Jackson's posthumous hit "This Is It" | Todd McClary | Shortz |
| Fri, Apr 23, 1999 | 1A | "Diana" singer | Harvey Estes | Shortz |
| Wed, Apr 19, 1995 | 10D | "Lonely Boy" singer | Alfio Micci | Shortz |
| Fri, Nov 04, 1994 | 43A | Singer from Ottawa | Matt Jones | Shortz |