| Date | Grid | Clue | Author | Editor |
| Wed, Feb 28, 2024 | 45D | Buffoonery | Greg Snitkin | Shortz |
| Sun, Feb 12, 2023 | 100D | Capers | Christina Iverson and Samuel A. Donaldson | Shortz |
| Sat, Nov 26, 2022 | 7A | High jinks | Kanyin Ajayi | Shortz |
| Fri, Oct 01, 2021 | 33D | Foolery | Jim Horne and Jeff Chen | Shortz |
| Sun, Aug 09, 2020 | 93D | Slapstick silliness | Ruth Bloomfield Margolin | Shortz |
| Tue, Jul 16, 2019 | 45D | Shenanigans | Ross Trudeau | Shortz |
| Wed, Jun 03, 2009 | 55A | Class clown's doings | Samuel A. Donaldson | Shortz |
| Tue, Jul 03, 2007 | 11D | Class clown's doings | Norma Johnson | Shortz |
| Thu, May 03, 2007 | 5D | Tomfoolery | Richard Chisholm | Shortz |
| Sun, Oct 09, 2005 | 35A | Monkey business | Kyle Mahowald | Shortz |
| Sun, Apr 03, 2005 | 101A | Capers | Nancy Nicholson Joline | Shortz |
| Sun, Feb 01, 2004 | 18D | The Three Stooges had many | Roy Leban | Shortz |
| Sun, Jan 26, 2003 | 112A | Monkeyshines | Nancy Salomon and Bob Peoples | Shortz |
| Sat, Feb 23, 2002 | 9A | Tricks | Rich Norris | Shortz |
| Wed, Jul 04, 2001 | 45A | Capers | John Beck | Shortz |
| Mon, Dec 13, 1999 | 4D | Monkeyshines | Dave and Diane Epperson | Shortz |
| Fri, Jul 16, 1999 | 16A | Harlequinade | Gerald R. Ferguson | Shortz |
| Wed, Aug 26, 1998 | 39A | Buffoonery | A. J. Santora | Shortz |
| Fri, Feb 28, 1997 | 6D | Funny business | Bob Klahn | Shortz |
| Tue, May 16, 1995 | 29D | Shenanigans | David J. Kahn | Shortz |
| Wed, Aug 17, 1994 | 45A | Shenanigans | Robert H. Wolfe | Shortz |
| Mon, Mar 28, 1994 | 25D | Clowning achievements? | William P. Baxley | Shortz |