| Date | Grid | Clue | Author | Editor |
| Wed, May 29, 2024 | 60A | Ruthless ruler | Jeanne Breen and Jeff Chen | Fagliano |
| Sun, Sep 20, 2020 | 44D | Oppressive ruler | Sam Trabucco | Shortz |
| Sun, Aug 21, 2016 | 66D | Tyrant | Kathy Matheson and Jeff Chen | Shortz |
| Tue, May 20, 2014 | 5D | Ruler who rules by force | Peter A. Collins | Shortz |
| Tue, Dec 17, 2013 | 43A | Ironfisted ruler | Paula Gamache | Shortz |
| Sun, Jun 21, 2009 | 60A | Kim Jong-il, e.g. | Matt Ginsberg and Pete Muller | Shortz |
| Mon, Oct 06, 2008 | 8D | Tyrant | Patrick Blindauer | Shortz |
| Wed, Sep 13, 2006 | 26A | Oppressor | Lee Glickstein and Nancy Salomon | Shortz |
| Thu, Nov 18, 2004 | 1D | Tyrant | Charles Barasch | Shortz |
| Wed, Jun 02, 2004 | 40D | Tyrant | Nancy Salomon | Shortz |
| Mon, Apr 12, 2004 | 73A | Tyrannical leader | Gail Grabowski | Shortz |
| Sun, Jul 06, 2003 | 129A | Papa Doc Duvalier, e.g. | Robert H. Wolfe | Shortz |
| Thu, Apr 27, 2000 | 69A | Saddam Hussein, e.g. | Greg Staples | Shortz |
| Sat, Oct 02, 1999 | 24A | Qaddafi, for one | Rich Norris | Shortz |
| Thu, Sep 02, 1999 | 52D | Ironfisted one | Joe DiPietro | Shortz |
| Mon, Jun 09, 1997 | 49A | Vlad the Impaler, e.g. | Thomas W. Schier | Shortz |
| Sun, May 04, 1997 | 12D | Democrat's opponent? | Manny Nosowsky | Shortz |
| Sun, Apr 27, 1997 | 112A | Saddam Hussein, e.g. | Matt Gaffney | Shortz |
| Sat, Feb 17, 1996 | 41A | Oppressor | Bob Sefick | Shortz |
| Sun, Nov 12, 1995 | 66A | Vlad the Impaler, e.g. | Randolph Ross | Shortz |
| Thu, Aug 25, 1994 | 47D | Ruthless ruler | Harvey Estes | Shortz |
| Thu, Jun 02, 1994 | 59A | Idi Amin, e.g. | Harvey Estes | Shortz |
| Wed, Apr 20, 1994 | 63A | Satrap | Walter Webb | Shortz |
| Sun, Mar 20, 1994 | 56D | Tyrant | Joel Davajan | Shortz |