| Date | Grid | Clue | Author | Editor |
| Sun, Sep 17, 2023 | 105A | Actress Chaplin | Jill Rafaloff and Michelle Sontarp | Shortz |
| Sun, Aug 28, 2022 | 102D | Chaplin of "Game of Thrones" | Ori Brian | Shortz |
| Wed, Nov 10, 2021 | 26D | Actress Chaplin | Max Chen Lauring and Benjamin Chen Lauring | Shortz |
| Fri, Sep 03, 2021 | 41A | Actress Chaplin | Brendan Emmett Quigley and Paolo Pasco | Shortz |
| Sun, Feb 21, 2021 | 82D | Actress Chaplin | Matthew Stock | Shortz |
| Thu, Dec 17, 2020 | 55A | Actress Chaplin | Kathryn Ladner | Shortz |
| Sun, Aug 25, 2019 | 19D | "Game of Thrones" actress Chaplin | Matt Ginsberg | Shortz |
| Tue, Aug 06, 2019 | 19D | Actress Chaplin of 53-Across | Jon Olsen | Shortz |
| Sun, Jun 23, 2019 | 69D | Actress Chaplin of "Game of Thrones" | David Liben-Nowell and Victor Barocas | Shortz |
| Thu, Jan 24, 2019 | 67D | A Chaplin | Stu Ockman | Shortz |
| Tue, Sep 11, 2018 | 25D | Actress Chaplin of "Game of Thrones" | Timothy Polin | Shortz |
| Tue, Oct 24, 2017 | 32A | Chaplin of "Game of Thrones" | Damon Gulczynski | Shortz |
| Tue, Jul 12, 2016 | 52A | "Game of Thrones" actress Chaplin | Samuel A. Donaldson | Shortz |
| Sat, Jul 02, 2016 | 6D | Chaplin of "Game of Thrones" | Erin Rhode | Shortz |
| Sun, May 08, 2016 | 37D | Chaplin of "Game of Thrones" | David J. Kahn | Shortz |
| Thu, Sep 24, 2015 | 18D | Chaplin of "Game of Thrones" | Peter A. Collins | Shortz |
| Fri, Jul 31, 2015 | 27A | Donald Duck cartoon princess | James Mulhern and Ashton Anderson | Shortz |
| Mon, Jun 08, 2015 | 56A | Actress Chaplin of "Game of Thrones" | Peter A. Collins | Shortz |
| Tue, Feb 17, 2015 | 15A | Wife of Charlie Chaplin | Bruce Haight | Shortz |
| Sun, Nov 02, 2014 | 117A | Chaplin of "Game of Thrones" | Brendan Emmett Quigley | Shortz |
| Sun, Feb 09, 2014 | 57A | An O'Neill | Charles M. Deber | Shortz |
| Wed, Jan 01, 2014 | 16A | ___ O'Neill | Peter A. Collins | Shortz |
| Sun, Nov 03, 2013 | 20A | Actress Chaplin of "Game of Thrones" | Andy Kravis and Victor Barocas | Shortz |
| Wed, Oct 02, 2013 | 15A | Charlie Chaplin's last wife | Paula Gamache | Shortz |
| Tue, Sep 10, 2013 | 12D | Wife of Charlie Chaplin | Zhouqin Burnikel | Shortz |
| Sun, Sep 08, 2013 | 56D | Actress Chaplin of "Game of Thrones" | Pete Muller and Sue Keefer | Shortz |
| Mon, May 13, 2013 | 68A | Mrs. Charlie Chaplin | Allan E. Parrish | Shortz |
| Sat, Mar 09, 2013 | 57D | Princess in Donald Duck cartoons | David Steinberg and Barry C. Silk | Shortz |
| Mon, Nov 26, 2012 | 14A | Wife of Charlie Chaplin | Ed Sessa | Shortz |
| Fri, Oct 12, 2012 | 14A | O'Neill whom J. D. Salinger wanted to marry | Martin Ashwood-Smith | Shortz |
| Sun, Jul 01, 2012 | 103A | The final Mrs. Chaplin | Dan Schoenholz | Shortz |
| Thu, Dec 29, 2011 | 30A | One of the Chaplins | David Steinberg | Shortz |
| Wed, Aug 17, 2011 | 38D | A Chaplin | Michael Black | Shortz |
| Fri, Jul 29, 2011 | 30A | Princess ___ (Disney duck) | Paula Gamache | Shortz |
| Thu, Jun 23, 2011 | 12D | Wife of Charlie Chaplin | Ian Livengood | Shortz |
| Mon, May 23, 2011 | 54D | Mrs. Chaplin | Steve Salitan | Shortz |
| Tue, Mar 10, 2009 | 15A | The last Mrs. Charlie Chaplin | Thomas Takaro | Shortz |
| Sun, Nov 16, 2008 | 50A | Young wife (age 18) of Charlie Chaplin (age 54) | Merl Reagle | Shortz |
| Fri, Aug 08, 2008 | 7D | 1998 biography subtitled "Living in the Shadows" | Mike Nothnagel | Shortz |
| Tue, Dec 18, 2007 | 31A | A Chaplin | Alan Arbesfeld | Shortz |
| Sun, Nov 11, 2007 | 89D | Biography subtitled "Living in the Shadows" | Alan Arbesfeld | Shortz |
| Wed, Oct 17, 2007 | 50D | The last Mrs. Chaplin | Paula Gamache | Shortz |
| Tue, Sep 11, 2007 | 3D | Mrs. Chaplin | Christina Houlihan Kelly | Shortz |
| Sun, Aug 12, 2007 | 109A | Mrs. Chaplin | Cathy Millhauser | Shortz |
| Sat, May 12, 2007 | 28D | Disney's Princess ___ | Rich Norris | Shortz |
| Tue, Jan 09, 2007 | 16A | A Chaplin | Ed Early | Shortz |
| Fri, Jul 21, 2006 | 42A | A Chaplin | Kyle Mahowald | Shortz |
| Tue, Apr 11, 2006 | 6D | A Chaplin | Lee Glickstein and Nancy Salomon | Shortz |
| Wed, Feb 22, 2006 | 15A | The last Mrs. Chaplin | Nancy Salomon | Shortz |
| Thu, Dec 08, 2005 | 12D | Mrs. Chaplin | David Pringle | Shortz |
| Thu, Sep 08, 2005 | 15A | A Mrs. Chaplin | Ben Tausig | Shortz |
| Mon, Aug 01, 2005 | 28A | Mrs. Chaplin | Kendall Twigg | Shortz |
| Sat, Jun 25, 2005 | 16A | 54-year-old Charlie's 18-year-old bride | John Underwood | Shortz |
| Wed, Feb 23, 2005 | 21A | Mrs. Chaplin | Lee Glickstein | Shortz |
| Mon, Jan 17, 2005 | 26D | Mrs. Chaplin | Alison Donald | Shortz |
| Thu, Dec 09, 2004 | 49D | Mrs. Chaplin | Paula Gamache | Shortz |
| Sun, Nov 14, 2004 | 20A | Mrs. Chaplin | Harvey Estes and Nancy Salomon | Shortz |
| Mon, Nov 01, 2004 | 14A | Mrs. Chaplin | Kendall Twigg and Nancy Salomon | Shortz |
| Mon, Jun 28, 2004 | 49D | One of the O'Neills | Sarah Keller | Shortz |
| Fri, May 28, 2004 | 32D | Mrs. Chaplin | Manny Nosowsky | Shortz |
| Tue, May 11, 2004 | 54A | Charlie Chaplin's widow | Lee Glickstein and Nancy Salomon | Shortz |
| Wed, Apr 07, 2004 | 40A | Geraldine Chaplin's mother | Nancy Salomon | Shortz |
| Fri, Feb 06, 2004 | 42A | Miss O'Neill | Joe DiPietro | Shortz |
| Fri, Jan 30, 2004 | 56D | Mrs. Chaplin | Manny Nosowsky | Shortz |
| Mon, Jan 12, 2004 | 21D | Mrs. Chaplin | Kurt Mengel | Shortz |
| Thu, Jul 24, 2003 | 15A | Eugene O'Neill's daughter | Rich Norris | Shortz |
| Fri, Mar 07, 2003 | 16A | Mrs. Chaplin | Harvey Estes | Shortz |
| Sun, Feb 23, 2003 | 87A | Chaplin née 39-Down | Nancy Salomon | Shortz |
| Tue, Feb 11, 2003 | 35A | A Chaplin | Myles Callum | Shortz |
| Wed, Dec 11, 2002 | 55D | Mrs. Chaplin | Alan Arbesfeld | Shortz |
| Fri, Aug 23, 2002 | 47D | Woman's name that's Irish for "unity" | Brendan Emmett Quigley | Shortz |
| Thu, Feb 28, 2002 | 53A | Mrs. Chaplin | Greg Staples | Shortz |
| Thu, Oct 04, 2001 | 55D | A Mrs. Chaplin | David J. Kahn | Shortz |
| Wed, Apr 04, 2001 | 46D | Mrs. Chaplin | Alan Arbesfeld | Shortz |
| Sun, Sep 03, 2000 | 107A | Mrs. Chaplin | David J. Kahn | Shortz |
| Mon, Jul 10, 2000 | 19A | Mrs. Chaplin | Gene Newman | Shortz |
| Wed, Jun 14, 2000 | 55A | The last Mrs. Chaplin | Nancy Salomon and Sherry O. Blackard | Shortz |
| Thu, Jun 01, 2000 | 57A | One of the O'Neills | David J. Kahn | Shortz |
| Wed, Apr 26, 2000 | 27D | A Chaplin | A. J. Santora | Shortz |
| Fri, Nov 05, 1999 | 44A | Mrs. Chaplin | Mark Diehl | Shortz |
| Wed, Dec 16, 1998 | 23A | Wife of Charlie Chaplin | Nancy Salomon | Shortz |
| Tue, Jul 14, 1998 | 15A | The last Mrs. Chaplin | Raymond Hamel | Shortz |
| Thu, Aug 07, 1997 | 61A | Mrs. Charles Chaplin | Mark Diehl | Shortz |
| Mon, Jun 09, 1997 | 64A | Mrs. Chaplin | Thomas W. Schier | Shortz |
| Tue, Oct 08, 1996 | 56A | Mrs. Chaplin | E. C. Gorski | Shortz |
| Mon, Sep 09, 1996 | 61A | One of the O'Neills | S. L. Robbins | Shortz |
| Wed, Jun 12, 1996 | 63A | Lady Chaplin | D. C. Baldwin | Shortz |
| Tue, May 21, 1996 | 54D | One of the O'Neills | J. Schmalzbach | Shortz |
| Sun, Mar 03, 1996 | 109D | Chaplin's widow | B. Klahn | Shortz |
| Wed, Feb 21, 1996 | 19A | Mrs. Chaplin | F. & L. Sabin | Shortz |
| Mon, Jan 15, 1996 | 10A | Mrs. Chaplin | Gregory E. Paul | Shortz |
| Sat, Sep 02, 1995 | 21D | An O'Neill | Manny Nosowsky | Shortz |
| Thu, Jul 06, 1995 | 8D | A Chaplin | David J. Kahn | Shortz |
| Sat, Apr 01, 1995 | 62D | Mrs. Chaplin | Fred Piscop | Shortz |
| Mon, Sep 26, 1994 | 26D | Mrs. Chaplin | Sidney L. Robbins | Shortz |
| Sat, Aug 27, 1994 | 51D | Lady Chaplin | Joy L. Wouk | Shortz |
| Thu, Jun 23, 1994 | 56A | One of the O'Neills | Trip Payne | Shortz |
| Mon, Jun 20, 1994 | 46D | Miss O'Neill | Bette Sue Cohen | Shortz |
| Thu, May 05, 1994 | 61A | The last Mrs. Chaplin | Mel Taub | Shortz |
| Tue, Jan 25, 1994 | 56A | Mrs. Chaplin | Joel Davajan | Shortz |
| Wed, Dec 08, 1993 | 14A | The last Mrs. Chaplin | Norma Steinberg | Shortz |