| Date | Grid | Clue | Author |
| Wed Apr 24, 2024 | 34D | Celebrity whose middle name is Gail, appropriately enough | Jeffrey Martinovic |
| Sun Mar 31, 2024 | 73D | Who cries "You get a car, you get a car!" in a viral meme | Spencer Leach |
| Sun Feb 11, 2024 | 10D | Talk show host nominated for an Academy Award | Peter Koetters |
| Mon Nov 6, 2023 | 12D | Longtime show host known as the "Queen of All Media" | Desirée Penner and Jeff Sinnock |
| Tue Oct 31, 2023 | 50D | Big name in media and philanthropy | Kathy Lowden and Erik Piepenburg |
| Fri Oct 13, 2023 | 45D | Highest-rated daytime talk show in American history | John-Clark Levin |
| Thu Aug 10, 2023 | 52D | Media mogul whose production company is her name in reverse | Natan Last and the J.A.S.A. Crossword Class |
| Tue Jan 31, 2023 | 25A | One-named "Queen of All Media" | Erik Agard |
| Sat Sep 10, 2022 | 40A | Co-host of the 1970s program "People Are Talking" | Kameron Austin Collins |
| Fri Jul 22, 2022 | 47A | First Black female billionaire, informally | David Steinberg |
| Wed Apr 6, 2022 | 17A | Celeb with a good friend named Gayle | Damon Gulczynski |
| Fri Jan 14, 2022 | 23A | Author of "What I Know for Sure," familiarly | Matthew Stock and Sid Sivakumar |
| Sun Jul 25, 2021 | 99D | Noted book club leader | Chandi Deitmer |
| Sun May 23, 2021 | 70D | High-profile interviewer of Harry and Meghan | Jennifer Nebergall |
| Sun Feb 7, 2021 | 18A | The "O" of OWN | Katie Hale and Christina Iverson |
| Sun Jan 17, 2021 | 111A | O icon | Tracy Gray and Tom Pepper |
| Fri Dec 25, 2020 | 54A | Book club leader on TV | Erik Agard and Wendy L. Brandes |
| Tue Dec 15, 2020 | 47A | Talk show queen named after a figure in Ruth | Adam Vincent |
| Sun Nov 1, 2020 | 68D | Host of an Apple TV+ book club | Julian Lim |
| Thu Jun 11, 2020 | 14A | Head of Harpo Productions | Peter A. Collins |
| Mon Dec 30, 2019 | 25D | What the "O" of O magazine stands for | Gary Larson |
| Tue Aug 13, 2019 | 6D | Founder of Harpo Productions | Lynn Lempel |
| Thu Apr 11, 2019 | 42D | She played Mrs. Which in 2018's "A Wrinkle in Time" | Brendan Emmett Quigley |
| Tue Apr 9, 2019 | 21A | Entertainer Marx / Entertainer Winfrey | Alex Eaton-Salners |
| Mon Aug 6, 2018 | 2D | The "O" of O magazine | Andrea Carla Michaels and Mark Diehl |
| Tue Mar 6, 2018 | 6D | Who said "I'm black. I don't feel burdened by it .... It's part of who I am. It does not define me" | Bruce Greig |
| Wed Jun 21, 2017 | 38A | The "O" of the magazine O | Bruce Haight |
| Fri Mar 17, 2017 | 46D | The "O" in television's OWN | Jacob Stulberg |
| Thu Jan 5, 2017 | 14A | She played Annie Lee in "Selma" | Ed Sessa |
| Tue Aug 9, 2016 | 11D | She's got her OWN network | Andrea Carla Michaels |
| Tue May 24, 2016 | 53D | Show on which Dr. Phil became famous, familiarly | Jonathan Gersch |
| Tue May 17, 2016 | 31D | O of the magazine world | Paula Gamache |
| Thu Apr 21, 2016 | 9D | TV personality with the best seller "What I Know for Sure" | Alex Bajcz |
| Wed Feb 10, 2016 | 52D | Celeb parodied by Maya Rudolph on "S.N.L." | John Guzzetta |
| Tue Nov 10, 2015 | 8D | O, The ___ Magazine | Will Treece |
| Sun Jul 12, 2015 | 55D | Actress in "Selma," familiarly | Patrick Berry |
| Wed Dec 24, 2014 | 2D | What "O" on a newsstand stands for | Adam G. Perl |
| Sat Jul 26, 2014 | 22D | Voice actress in Disney's "The Princess and the Frog" | Julian Lim |
| Thu May 29, 2014 | 25D | Media icon with an eponymous Starbucks beverage | Anna Shechtman |
| Tue Jan 24, 2012 | 52D | Noted talk show retiree of 2011 | Alex Boisvert |
| Tue Nov 1, 2011 | 63A | What "O" stands for in the magazine business | Kristian House |
| Sun Jul 24, 2011 | 22A | Hit TV show that ended in 2011 | Kurt Mueller |
| Sun Dec 5, 2010 | 35D | Long-running hit TV show based in Chicago | Ben Pall |
| Sun Oct 10, 2010 | 47D | First name in TV talk (2) | Patrick Merrell |
| Fri Apr 30, 2010 | 24A | Player of Sethe in "Beloved" | Natan Last |
| Thu Apr 15, 2010 | 52A | Co-producer of the film "Precious" | Brendan Emmett Quigley & Joon Pahk |
| Tue Sep 1, 2009 | 2D | TV host with a book club (2) | Steven Ginzburg |
| Sun Jul 19, 2009 | 94D | Big name in daytime TV (3) | Lynn Lempel |
| Mon Apr 20, 2009 | 14A | Winfrey who said "I still have my feet on the ground, I just wear better shoes" | Randall J. Hartman |
| Wed Oct 15, 2008 | 2D | She played Sofia in "The Color Purple" | Kevin G. Der |
| Tue Jul 29, 2008 | 28D | First name in book clubs | David Kwong and Emily Halpern |
| Wed Jul 2, 2008 | 5A | Daytime TV staple (3) | Daniel Kantor |
| Sun May 20, 2007 | 33D | Longtime staple of daytime TV | Seth A. Abel |
| Sun Feb 25, 2007 | 41A | Show taped at Chicago's Harpo Studios | David J. Kahn |
| Mon Dec 11, 2006 | 14D | TV host with a book club (2) | David J. Kahn |
| Thu Oct 26, 2006 | 6D | Daily TV staple since 1986 | Todd McClary and Dave Tuller |
| Mon Sep 11, 2006 | 23A | Chicago-based TV talk show | Lynn Lempel |
| Sat Jul 1, 2006 | 23A | Friend of Dr. Phil | Jim Page |
| Mon Apr 24, 2006 | 1A | First name in daytime talk | Lynn Lempel |
| Sun Jan 29, 2006 | 91D | Book club name (2) | Rich Norris |
| Tue Jun 28, 2005 | 53D | Where Dr. Phil got famous | Jim Hyres |
| Sat Jan 29, 2005 | 10A | Show of compassion? | Patrick Berry |
| Mon Dec 6, 2004 | 51A | TV host Winfrey | Barry C. Silk |
| Sun Sep 26, 2004 | 73D | What "O" stands for in publishing | Joe DiPietro |
| Fri Apr 16, 2004 | 62A | Book club name (2) | Ed Early |
| Sun Oct 26, 2003 | 47D | Daytime TV staple (3) | Patrick Merrell |
| Tue Oct 7, 2003 | 30D | Colleague of Dr. Phil | Steve Jones |
| Sun Dec 1, 2002 | 20A | Big fan of Dr. Phil | David J. Kahn |
| Sun Mar 17, 2002 | 91A | Big name in book clubs (3) | David J. Kahn |
| Sun Nov 4, 2001 | 1D | Popular afternoon host | Manny Nosowsky |
| Fri Jan 26, 2001 | 24D | Sofia's portrayer in "The Color Purple" (2) | Joe DiPietro |
| Mon Jan 8, 2001 | 39D | TV's Winfrey (2) | Gregory E. Paul |
| Wed Oct 25, 2000 | 16A | Afternoon TV staple | Nick Grivas |
| Sun Oct 8, 2000 | 65D | First name in daytime TV | Richard Silvestri |
| Sun Jun 11, 2000 | 69D | Big name in book clubs (3) | Nelson Hardy |
| Thu May 11, 2000 | 6D | First name in TV talk (2) | Peter Abide |
| Fri Apr 21, 2000 | 16A | Daytime TV staple (3) | Mark Diehl |
| Sat Sep 11, 1999 | 6D | Big name in book clubs (3) | Rich Norris |
| Thu Jul 15, 1999 | 30A | Big name in daytime TV (3) | Zack Butler |
| Sat Mar 20, 1999 | 3D | Sofia's portrayer in "The Color Purple" (2) | Chuck Deodene |
| Mon Feb 22, 1999 | 5A | Big name in daytime TV (3) | Gregory E. Paul |
| Wed Oct 22, 1997 | 51D | Geraldo competitor | John D. Leavy |
| Thu Nov 2, 1995 | 28D | Competitor of Montel | Wayne Robert Williams |
| Mon Oct 16, 1995 | 15A | TV's Winfrey (2) | Bernice Gordon |
| Thu Sep 21, 1995 | 25D | Afternoon TV name | Chuck Deodene |
| Wed Dec 7, 1994 | 27D | Competitor of Phil | Chet Currier |
| Wed Aug 3, 1994 | 25D | Rival of Sally | Richard Thomas |
| Fri Jun 24, 1994 | 43D | Chicago-based TV show | Mark Diehl |
| Mon Jun 20, 1994 | 36A | Competition for Geraldo | Bette Sue Cohen |