| Date | Grid | Clue | Author | Editor |
|---|---|---|---|---|
| Sun, Aug 20, 2023 | 53D | Singer with the 2001 #1 hit "Fallin'" | Michael Schlossberg | Shortz |
| Fri, Dec 14, 2012 | 29D | 2001 Best New Artist Grammy winner | Paula Gamache | Shortz |
| Thu, Feb 05, 2009 | 30A | Singer/songwriter who received a 7-Down (2002, 2004-06, 2008) | David J. Kahn | Shortz |