| Date | Grid | Clue | Author |
| Tue Feb 15, 2022 | 48D | Comedian Anne | Claire Rimkus |
| Fri Feb 4, 2022 | 15D | Comic partner of Stiller | Joseph Greenbaum |
| Wed Apr 7, 2021 | 67A | Stiller's comedy partner (5) | Adrian Johnson |
| Thu Feb 11, 2021 | 22A | Actress Anne with four Emmy nominations | Alex Eaton-Salners |
| Sat Aug 22, 2020 | 7D | Half of a classic comedy duo (2) | Trenton Charlson |
| Fri Jul 26, 2019 | 44A | Half of an old comedy duo (2) | Trenton Charlson |
| Sun May 26, 2019 | 107D | Stiller's comic partner (2) | Ruth Bloomfield Margolin |
| Fri Mar 29, 2019 | 3D | Funny Anne (5) | Martin Ashwood-Smith |
| Tue Nov 20, 2018 | 20A | Stiller's partner in comedy (5) | Zhouqin Burnikel |
| Thu Jun 7, 2018 | 25D | Anne of comedy (2) | Bruce Haight |
| Tue Apr 4, 2017 | 32D | Stiller's longtime wife and comedy partner | Timothy Polin |
| Sun Dec 22, 2013 | 98A | Funny Anne (5) | Elizabeth C. Gorski |
| Tue Apr 2, 2013 | 51A | Stiller's partner in comedy (5) | Ian Livengood |
| Mon Sep 17, 2012 | 22A | Stiller's partner in comedy (5) | Adam G. Perl |
| Mon Jul 2, 2012 | 15A | Stiller's partner in comedy (5) | Bernice Gordon |
| Wed Jul 28, 2010 | 53D | Anne of "Archie Bunker's Place" | Howard Baker |
| Tue May 25, 2010 | 60A | Stiller's partner in comedy (5) | Sarah Keller |
| Mon May 10, 2010 | 40A | Stiller and ___ (comedy duo) | Randy Sowell |
| Sat Jan 16, 2010 | 16A | Comic actress who co-starred on "Archie Bunker's Place" | Ned White |
| Thu Nov 19, 2009 | 9D | Anne whose real-life husband played her ex on "Rhoda" | Tyler Hinman and Jeremy Horwitz |
| Sun Oct 11, 2009 | 69D | Stiller and ___ (2) | Randolph Ross |
| Sat May 9, 2009 | 39A | Tony award nominee for "Anna Christie," 1993 | Brad Wilber |
| Wed Dec 24, 2008 | 53D | Stiller's comedy partner (5) | Warren Biro |
| Wed Dec 10, 2008 | 41D | Stiller's partner | Joe Krozel |
| Wed Jul 23, 2008 | 65A | Stiller's comic partner (2) | Henry Quillen |
| Thu Jun 5, 2008 | 12D | Half of a popular comedy team | James Sajdak |
| Wed Mar 28, 2007 | 11D | Comic Anne | Burton Clemans |
| Sun Sep 24, 2006 | 53D | Anne of comedy (2) | Mark Diehl and Kevin McCann |
| Wed Aug 2, 2006 | 36A | See 34-Down | Harvey Estes |
| Sat Jul 22, 2006 | 19A | Half of an old comedy duo (2) | Robert H. Wolfe |
| Fri Nov 25, 2005 | 24A | Half a comedy duo (2) | Joe DiPietro |
| Tue Jul 26, 2005 | 32A | Stiller's comedy partner (5) | Lee Glickstein and Nancy Salomon |
| Sat Oct 2, 2004 | 15D | "The Daytrippers" actress, 1996 | David J. Kahn |
| Sun Jan 25, 2004 | 14A | Half of a classic comedy duo (2) | Harvey Estes and Nancy Salomon |
| Sun Dec 22, 2002 | 68D | Funny Anne (5) | Frances Hansen |
| Fri Feb 22, 2002 | 52D | Funny Anne (5) | Elizabeth C. Gorski |
| Thu Aug 30, 2001 | 48D | Half a comedy duo (2) | Cathy Millhauser |
| Fri Dec 17, 1999 | 47D | Half of a well-known comedy duo | Manny Nosowsky |
| Thu May 27, 1999 | 38D | Half of a noted comedy team | A. J. Santora |
| Tue Oct 28, 1997 | 34D | Stiller's comedy partner (5) | Bernice Gordon |
| Sun Aug 10, 1997 | 43D | She's still with Stiller | Nancy Nicholson Joline |
| Sun Apr 27, 1997 | 63A | Stiller's comedy partner (5) | Matt Gaffney |
| Tue Dec 31, 1996 | 5A | Stiller and ___ (2) | A. S. Verdesca |
| Sun Mar 24, 1996 | 111D | Half a famous comedy duo | J. K. Brill |
| Fri Jan 5, 1996 | 25A | Half of a famous comic duo | R. Ross |
| Sat Nov 5, 1994 | 1D | Half of a comedy team | Manny Nosowsky |
| Fri Aug 26, 1994 | 55A | Comical Anne | Timothy S. Lewis |
| Thu Jul 28, 1994 | 9A | Funny Anne (5) | Bryant White |
| Fri Jun 10, 1994 | 44A | Actress Anne | Wayne Robert Williams |