| Date | Grid | Clue | Author | Editor |
| Sat, Jul 29, 2023 | 34A | Simple sort | Sam Ezersky | Shortz |
| Wed, Jun 29, 2022 | 53D | Cartoonist Goldberg who drew contraptions like the "Self-Operating Napkin" | Jared Goudsmit | Shortz |
| Fri, Sep 10, 2021 | 33A | Clodhopper | Adrian Kabigting | Shortz |
| Tue, Sep 15, 2020 | 44A | Naïve sort | Amanda Rafkin and Ross Trudeau | Shortz |
| Wed, May 22, 2019 | 2D | Naïve sort | Alex Eaton-Salners | Shortz |
| Thu, Mar 15, 2018 | 9A | Yahoo | Joe DiPietro | Shortz |
| Sat, Feb 17, 2018 | 49D | Carny's target | Peter Wentz | Shortz |
| Mon, Apr 18, 2016 | 23A | Unsophisticated sort | Janice Luttrell | Shortz |
| Fri, Aug 08, 2014 | 55A | No sophisticate | Bruce Haight | Shortz |
| Thu, May 29, 2014 | 37A | Simpleton | Anna Shechtman | Shortz |
| Wed, Feb 05, 2014 | 16A | Con artist's mark | Tracy Gray | Shortz |
| Thu, May 16, 2013 | 62A | Hayseed | Brendan Emmett Quigley and Elizabeth Donovan | Shortz |
| Sun, Sep 20, 2009 | 81D | Bumpkin | Michael Ashley | Shortz |
| Thu, Apr 09, 2009 | 14A | Potential sucker | Patrick Blindauer and Tony Orbach | Shortz |
| Fri, Feb 13, 2009 | 20A | Potential sucker | Doug Peterson | Shortz |
| Sun, Dec 17, 2006 | 55D | Rustic | Joe DiPietro | Shortz |
| Tue, Jun 27, 2006 | 61D | Unsophisticated sort | Damon J. Gulczynski | Shortz |
| Sun, Jun 11, 2006 | 6D | Any of TV's Clampetts | Maxwell H. D. Johnson Jr. | Shortz |
| Thu, Feb 03, 2005 | 64A | Country cousin | Elizabeth C. Gorski | Shortz |
| Thu, Jan 13, 2005 | 32A | Hick | Robert Zimmerman | Shortz |
| Wed, Mar 12, 2003 | 35D | Sticks figure | Myles Callum | Shortz |
| Fri, Oct 18, 2002 | 41A | Rustic | Manny Nosowsky | Shortz |
| Fri, Oct 11, 2002 | 39D | "Hee Haw" character | A. J. Santora | Shortz |
| Sun, Jun 16, 2002 | 81A | Hardly a sophisticate | Manny Nosowsky | Shortz |
| Mon, Nov 12, 2001 | 4D | Unsophisticated sort | Janice M. Putney | Shortz |
| Tue, May 22, 2001 | 49D | Bumpkin | John D. Leavy | Shortz |
| Sun, Aug 13, 2000 | 1D | Hick | Nancy Salomon and Harvey Estes | Shortz |
| Sun, Apr 09, 2000 | 41D | Sticks figure | Joe DiPietro | Shortz |
| Wed, Dec 15, 1999 | 3D | Yokel | Ethan Cooper | Shortz |
| Tue, Sep 21, 1999 | 10A | Country bumpkin | Stephanie Spadaccini | Shortz |
| Mon, Aug 24, 1998 | 53D | Hick | Alan Jay Weiss | Shortz |
| Tue, Mar 31, 1998 | 9A | Country bumpkin | Alan Arbesfeld | Shortz |
| Thu, Dec 11, 1997 | 39D | Yokel | Trip Payne | Shortz |
| Sun, Jun 08, 1997 | 1D | Rustic | Richard Silvestri | Shortz |
| Thu, Jun 06, 1996 | 56A | Hick | A. J. Santora | Shortz |
| Tue, Mar 12, 1996 | 19A | Hick | R. J. Hartman | Shortz |
| Wed, Aug 03, 1994 | 53D | Hayseed | Richard Thomas | Shortz |
| Thu, May 26, 1994 | 52D | "Mike and Ike" creator Goldberg | Cathy Millhauser | Shortz |
| Thu, Feb 10, 1994 | 11D | Hick | Manny Nosowsky | Shortz |
| Wed, Jan 12, 1994 | 54A | Bumpkin | Fred Piscop | Shortz |
| Thu, Jan 06, 1994 | 14A | Rustic | Arthur W. Palmer | Shortz |