| Date | Grid | Clue | Author | Editor |
| Sun Oct 12, 2025 | 121A | John, across the pond | Michael Schlossberg | Shortz |
| Thu May 29, 2025 | 34D | Younger Lennon son | John Kugelman | Shortz |
| Fri Dec 13, 2024 | 52D | Bean on the screen | Ryan Patrick Smith | Fagliano |
| Sun Apr 28, 2024 | 77A | Lennon who co-wrote the Oscar-winning short "War Is Over!" | Mike Ellison | Fagliano |
| Wed Mar 20, 2024 | 61D | Irish version of 40-Down | E. M. Capassakis | Fagliano |
| Fri Feb 3, 2023 | 53A | Name written with an accent in Irish English | Barbara Lin | Shortz |
| Mon Oct 17, 2022 | 29D | Connery who played James Bond seven times | Caryn L. Robbins | Shortz |
| Sun Oct 2, 2022 | 27A | Actor Astin | Kathy Bloomer | Shortz |
| Sun May 1, 2022 | 151A | John, abroad (2) | Brandon Koppy | Shortz |
| Thu Feb 24, 2022 | 31D | With 6-Down, former White House press secretary portrayed by Melissa McCarthy on "S.N.L." | Jake Halperin | Shortz |
| Thu Dec 9, 2021 | 40D | John, abroad (2) | Alexander Liebeskind | Shortz |
| Tue Oct 26, 2021 | 23A | Connery who played 007 seven times | Michael Schlossberg | Shortz |
| Fri Mar 12, 2021 | 57A | Parker who served as the first president of Facebook | Peter Wentz | Shortz |
| Fri Aug 21, 2020 | 39A | ___ Combs a.k.a. Diddy | Alex Eaton-Salners | Shortz |
| Wed Apr 1, 2020 | 70A | One of the Lennons (4) | John Ficarra and Patrick Merrell | Shortz |
| Thu Dec 5, 2019 | 3D | Penn name (6) | Neville Fogarty | Shortz |
| Sun Nov 10, 2019 | 50D | Bean on the silver screen | Peter Gordon | Shortz |
| Thu Jun 13, 2019 | 63A | Parker who was the first president of Facebook | Michael Blake and Jeff Chen | Shortz |
| Sun Mar 4, 2018 | 36A | Irish "John" | Byron Walden | Shortz |
| Sun Feb 25, 2018 | 14D | Jamaican rapper ___ Paul | Will Nediger | Shortz |
| Wed Jan 24, 2018 | 43A | Son of John and Yoko (2) | Kathy Wienberg | Shortz |
| Sun May 28, 2017 | 13D | Trump spokesman Spicer | Andrew Zhou | Shortz |
| Sun Apr 2, 2017 | 114D | White House spokesman Spicer | Jerry Miccolis | Shortz |
| Wed Dec 7, 2016 | 38D | Actor Penn of "Milk" | David Steinberg | Shortz |
| Tue Apr 26, 2016 | 39D | Actor Bean, whose first name looks like it rhymes with his last, but doesn't | Finn Vigeland | Shortz |
| Fri Jun 12, 2015 | 41A | Jay ___, British singer with the 2009 #1 hit "Down" | David Steinberg | Shortz |
| Sat Feb 28, 2015 | 24A | Bean seen on-screen | Barry C. Silk | Shortz |
| Mon Jan 26, 2015 | 62A | Ian : Scotland :: ___ : Ireland | Ian Livengood | Shortz |
| Sat Oct 25, 2014 | 60A | Actor Bean of "Troy" | Patrick Blindauer | Shortz |
| Wed Sep 3, 2014 | 62A | ___ Parker, first president of Facebook | Peter A. Collins | Shortz |
| Sat Jun 21, 2014 | 6D | ___ Parker, founding president of Facebook | Brad Wilber and Byron Walden | Shortz |
| Sun Jun 8, 2014 | 44D | With 103-Down, "Hurlyburly" star | Patrick Berry | Shortz |
| Sun Jun 23, 2013 | 53D | Playwright O'Casey (4) | Patrick Berry | Shortz |
| Sun Sep 30, 2012 | 102D | One of the Lennons (4) | Elayne Cantor and Victor Fleming | Shortz |
| Tue Sep 25, 2012 | 7D | Reggae artist ___ Paul | Ian Livengood | Shortz |
| Tue Nov 1, 2011 | 65A | Son of John and Yoko (2) | Kristian House | Shortz |
| Fri Jul 29, 2011 | 9D | Parker who was one of the original faces at Facebook | Paula Gamache | Shortz |
| Sat Apr 9, 2011 | 66A | Roger's predecessor as 007 | Scott Atkinson | Shortz |
| Wed Jan 26, 2011 | 32D | Rapper Combs a k a Diddy | David Murchie | Shortz |
| Thu Dec 23, 2010 | 26D | Reggae/dancehall artist ___ Paul | Oliver Hill and Eliza Bagg | Shortz |
| Mon Nov 22, 2010 | 17A | Actor Penn with two 23-Across | David Poole | Shortz |
| Sun Nov 21, 2010 | 55D | A Lennon | Clive Probert | Shortz |
| Fri Sep 3, 2010 | 53D | With 62-Across, subject of "Beautiful Boy (Darling Boy)" | John Farmer | Shortz |
| Thu Sep 4, 2008 | 38D | Grammy-winning reggae artist ___ Paul | Matt Ginsberg | Shortz |
| Sat Aug 9, 2008 | 52A | P. Diddy's first name | Mark Diehl | Shortz |
| Sat Dec 29, 2007 | 44D | Name equivalent to Hans or Ivan | Bob Klahn | Shortz |
| Mon Oct 15, 2007 | 46D | Actor Penn (3) | Andrea Carla Michaels | Shortz |
| Fri Jun 22, 2007 | 39A | "Blade Runner" actress Young | Mike Nothnagel | Shortz |
| Mon Apr 2, 2007 | 6D | Actor Penn (3) | Richard Hughes | Shortz |
| Tue Nov 8, 2005 | 21A | One of the Lennons (4) | Gail Grabowski and Nancy Salomon | Shortz |
| Sat Oct 15, 2005 | 6D | Penn name (6) | Paula Gamache | Shortz |
| Sun Oct 9, 2005 | 73A | Astin of "Lord of the Rings" (2) | Kyle Mahowald | Shortz |
| Sun Aug 7, 2005 | 26A | Playwright O'Casey (4) | Lee Glickstein and Nancy Salomon | Shortz |
| Mon Aug 1, 2005 | 5D | Actor Connery (2) | Kendall Twigg | Shortz |
| Wed Sep 8, 2004 | 67A | John Astin's actor son | Steve Jones | Shortz |
| Sun Aug 29, 2004 | 52A | Actor Penn (3) | Manny Nosowsky | Shortz |
| Sun Aug 1, 2004 | 53D | Astin of "Lord of the Rings" (2) | Randolph Ross | Shortz |
| Mon May 31, 2004 | 60D | Actor Connery (2) | Gregory E. Paul | Shortz |
| Sun Apr 18, 2004 | 74A | Penn of "Mystic River" | Richard Chisholm | Shortz |
| Thu Apr 10, 2003 | 57D | One of the Lennons (4) | Chuck Menning and Mitch Komro | Shortz |
| Fri Jan 3, 2003 | 30D | Bean of "The Lord of the Rings" | Jim Page | Shortz |
| Thu Aug 2, 2001 | 35A | Singer Lennon | Bruce F. Adams | Shortz |
| Mon Jul 16, 2001 | 61A | Puffy Combs's first name | Peter Gordon | Shortz |
| Tue Feb 13, 2001 | 62D | Rapper Combs | Michael Shteyman | Shortz |
| Mon Jun 26, 2000 | 62A | Young Lennon | Peter Gordon | Shortz |
| Sun Jan 30, 2000 | 77A | Penn name (6) | Peter Gordon | Shortz |
| Mon Jan 10, 2000 | 66A | Connery of 007 fame | John Greenman | Shortz |
| Sat Jul 24, 1999 | 47A | Actress Young (2) | Rich Norris | Shortz |
| Tue Jun 8, 1999 | 43D | Penn or Connery | Fred Piscop | Shortz |
| Tue Dec 22, 1998 | 13D | Penn name (6) | Adam Cohen | Shortz |
| Wed Oct 7, 1998 | 13D | O'Casey or O'Faoláin | Randall J. Hartman | Shortz |
| Tue Jun 23, 1998 | 29A | Playwright O'Casey (4) | Rich Norris | Shortz |
| Thu Jul 24, 1997 | 27D | Writer O'Faolain | Randall J. Hartman | Shortz |
| Sun Jun 1, 1997 | 28A | Penn name (6) | Randolph Ross | Shortz |
| Fri Feb 28, 1997 | 2D | Hans, in Ireland | Bob Klahn | Shortz |
| Wed Nov 13, 1996 | 51A | O'Casey or Penn | M. Nosowsky | Shortz |
| Tue Apr 4, 1995 | 48D | Mr. Connery | David J. Kahn | Shortz |
| Sun Nov 13, 1994 | 37D | Hollywood's Penn | Frank A. Longo | Shortz |
| Sun May 22, 1994 | 44A | Penn name (6) | Randolph Ross | Shortz |
| Tue May 3, 1994 | 66A | Actress Young (2) | Lois Sidway | Shortz |
| Tue Feb 1, 1994 | 29A | Playwright O'Casey (4) | Robert Zimmerman | Shortz |