| Date | Grid | Clue | Author | Editor |
| Wed, Mar 20, 2013 | 37A | Bandleader Kay | Raymond C. Young | Shortz |
| Tue, Sep 04, 2012 | 68A | Bandleader Kay | Barry Franklin and Sara Kaplan | Shortz |
| Sat, Oct 08, 2011 | 53D | Bandleader with the hit "Three Little Fishies" | Tim Croce | Shortz |
| Sun, Aug 08, 2010 | 100D | Orchestra leader Kay | Pam Klawitter | Shortz |
| Sun, Aug 15, 2004 | 149A | Bandleader Kay | Brendan Emmett Quigley | Shortz |
| Wed, Jul 30, 2003 | 33D | Radio Hall of Fame inductee Kay | Alan J. Weiss | Shortz |
| Wed, Apr 22, 1998 | 13D | 30's-40's bandleader Kay | Brendan Emmett Quigley | Shortz |
| Wed, Jul 23, 1997 | 12D | Bandleader Kay | Brendan Emmett Quigley | Shortz |