| Date | Grid | Clue | Author | Editor |
| Sat, Jan 20, 2024 | 20D | Jazz trumpeter Woody | Caitlin Reid and Matthew Stock | Shortz |
| Sun, Oct 24, 2021 | 65A | Playwright who wrote "Those who cannot change their minds cannot change anything" | Katie Hale | Shortz |
| Fri, May 29, 2020 | 6D | Playwright who wrote "All great truths begin as blasphemies" | Sam Ezersky | Shortz |
| Wed, Mar 04, 2020 | 29D | "Major Barbara" playwright | Tracy Gray | Shortz |
| Thu, Feb 06, 2020 | 14A | Title partner of Hobbs in a hit 2019 film | Jake Halperin | Shortz |
| Thu, Oct 25, 2018 | 57D | "Saint Joan" playwright | Neville Fogarty | Shortz |
| Fri, Aug 31, 2018 | 14D | Playwright who wrote "Walk! Not bloody likely. I am going in a taxi" | Peter Wentz | Shortz |
| Wed, Aug 22, 2018 | 1A | Eliza Doolittle's creator | John Lampkin | Shortz |
| Sun, Jul 22, 2018 | 79D | Who wrote "All great truths begin as blasphemies" | Patrick Merrell | Shortz |
| Sun, Apr 15, 2018 | 40A | "Man and Superman" playwright | Alex Bajcz | Shortz |
| Fri, Jul 14, 2017 | 50A | Playwright who wrote "Hell is full of musical amateurs" | Patrick Berry | Shortz |
| Wed, Aug 10, 2016 | 9D | "Arms and the Man" playwright | David C. Duncan Dekker | Shortz |
| Sun, Sep 21, 2014 | 1D | Only Literature Nobelist also to win an Oscar | Michael Ashley | Shortz |
| Wed, Dec 12, 2012 | 38D | Creator of Eliza Doolittle | Peter A. Collins | Shortz |
| Tue, May 01, 2012 | 10A | "Pygmalion" playwright | Zoe Wheeler and Aimee Lucido | Shortz |
| Tue, Mar 13, 2012 | 70A | "Man and Superman" playwright | Jeff Chen | Shortz |
| Thu, Apr 07, 2011 | 23A | Bernard formerly of CNN | Henry Hook | Shortz |
| Thu, Mar 24, 2011 | 65A | The 1999 comedy "She's All That" is based on his work | Ian Livengood | Shortz |
| Fri, Jan 28, 2011 | 26A | 1925 Literature Nobelist | Kevin G. Der | Shortz |
| Tue, Jul 27, 2010 | 6D | Clarinetist Artie | Mike Torch | Shortz |
| Sat, Jul 17, 2010 | 44A | "Fanny's First Play" playwright | Mark Diehl | Shortz |
| Sun, Mar 21, 2010 | 114D | Only man to win both a Nobel Prize and an Oscar | Adam Fromm | Shortz |
| Thu, Feb 18, 2010 | 21A | Who wrote "Hell is full of musical amateurs" | Caleb Madison | Shortz |
| Wed, Oct 07, 2009 | 1D | Henry Higgins's creator | Tim Wescott | Shortz |
| Thu, Jan 22, 2009 | 37D | "Rich Man, Poor Man" novelist, 1970 | Gary J. Whitehead | Shortz |
| Thu, Jul 03, 2008 | 65A | Irwin who wrote "Rich Man, Poor Man" | Keith Talon | Shortz |
| Thu, Dec 20, 2007 | 11D | "Saint Joan" playwright | Peter A. Collins | Shortz |
| Sat, Nov 10, 2007 | 60A | "Saint Joan" playwright | Dana Motley | Shortz |
| Thu, Jun 28, 2007 | 25D | "Major Barbara" playwright | Joseph Crowley | Shortz |
| Sun, May 20, 2007 | 102D | Newsman Bernard | Seth A. Abel | Shortz |
| Wed, Feb 21, 2007 | 1D | "Pygmalion" playwright | Elizabeth C. Gorski | Shortz |
| Thu, Oct 13, 2005 | 46D | Writer of "Saint Joan" | Patrick Merrell | Shortz |
| Sun, Mar 13, 2005 | 124A | "My Fair Lady" is based on his work | Patrick Merrell | Shortz |
| Wed, May 12, 2004 | 1D | Clarinetist Artie | Allan E. Parrish | Shortz |
| Wed, Nov 20, 2002 | 31A | Three-time Indy winner Wilbur ___, who introduced the crash helmet | Manny Nosowsky | Shortz |
| Sun, Nov 03, 2002 | 1D | "Man and Superman" playwright | Patrick Berry | Shortz |
| Wed, Oct 10, 2001 | 44A | "Pygmalion" playwright | Richard Chisholm | Shortz |
| Wed, Sep 26, 2001 | 53D | Clarinetist Artie | Stephen Budiansky | Shortz |
| Thu, Jan 18, 2001 | 10A | "Bury the Dead" playwright | Manny Nosowsky | Shortz |
| Wed, Dec 06, 2000 | 38D | "Mrs. Warren's Profession" writer | Mel Taub (and crossword class) | Shortz |
| Sun, Sep 03, 2000 | 9D | "Rich Man, Poor Man" novelist | David J. Kahn | Shortz |
| Mon, Jun 05, 2000 | 29A | Clarinetist Artie | William A. Ballard | Shortz |
| Thu, Oct 07, 1999 | 11D | "Begin the Beguine" bandleader | Kelly Clark | Shortz |
| Wed, Mar 10, 1999 | 54D | "Pygmalion" dramatist | Wesley R. Johnson | Shortz |
| Tue, Jun 16, 1998 | 53D | "Pygmalion" writer | Bill Ballard | Shortz |
| Tue, May 12, 1998 | 1A | "Candida" playwright | Elizabeth C. Gorski | Shortz |
| Sun, Mar 15, 1998 | 59D | CNN anchor Bernard | Frank Longo | Shortz |
| Fri, Feb 06, 1998 | 21A | "Heartbreak House" writer | Wayne Robert Williams | Shortz |
| Fri, Jan 10, 1997 | 52A | "Heartbreak House" writer | A. J. Santora | Shortz |
| Fri, Oct 18, 1996 | 1D | "Heartbreak House" playwright | M. Gaffney | Shortz |
| Sun, Jun 23, 1996 | 92D | Major Barbara's creator | F. Hansen | Shortz |
| Sat, Jul 22, 1995 | 57A | Newsman Bernard | Richard Thomas | Shortz |
| Mon, Jan 09, 1995 | 5A | "Arms and the Man" playwright | Sidney L. Robbins | Shortz |
| Tue, May 17, 1994 | 53D | "Saint Joan" playwright | Harvey Estes | Shortz |
| Mon, May 16, 1994 | 57A | Author Irwin | Ed Pegg Jr. | Shortz |
| Fri, Apr 08, 1994 | 18A | "Candida" playwright | David A. Rosen | Shortz |
| Wed, Mar 09, 1994 | 1A | "Major Barbara" playwright | Norma Steinberg | Shortz |
| Fri, Dec 03, 1993 | 2D | "Pygmalion" author | Bill Click | Shortz |