| Date | Grid | Clue | Author |
| Thu Mar 21, 2024 | 42A | "___ cosa fai?" (Italian for "What are you doing?") | Joe Marquez |
| Fri Mar 8, 2024 | 51D | Michael of "Saturday Night Live" (2) | Jackson Matz |
| Fri Dec 29, 2023 | 45A | Role in "Evita" | Robyn Weintraub |
| Thu Dec 7, 2023 | 33D | Subject of the classic photo "Guerrillero Heroico" | Rebecca Goldstein |
| Tue Sep 26, 2023 | 47A | ___ Guevara (revolutionary) | Shannon Rapp and Rebecca Goldstein |
| Tue Jun 27, 2023 | 22A | Beret-wearing rebel, familiarly | Anthony Gisonda |
| Thu May 11, 2023 | 57D | Tony-winning role for Mandy Patinkin (2) | Sheldon Polonsky |
| Sat Jan 28, 2023 | 39A | Comedian Michael | Kevin Christian |
| Wed Feb 9, 2022 | 24D | That, in Italian | Grant Thackray |
| Tue Dec 28, 2021 | 51A | Michael of "S.N.L." (2) | Kathy Wienberg |
| Tue Oct 12, 2021 | 52D | Revolutionary Guevara (10) | Conor Sefkow |
| Sun Apr 11, 2021 | 87A | Revolutionary Guevara (10) | Dick Shlakman and Will Nediger |
| Sun Mar 14, 2021 | 18A | His face overlooks Havana's Plaza de la Revolución | Jacob Stulberg |
| Thu Feb 18, 2021 | 46A | Revolutionary icon (2) | Zachary Spitz |
| Wed Jan 27, 2021 | 38A | What's what, in Italy (2) | Mike Knobler |
| Fri Apr 24, 2020 | 6D | Castro comrade | John Guzzetta |
| Tue Feb 25, 2020 | 46A | Michael of "S.N.L." (2) | Peter Gordon |
| Thu Oct 10, 2019 | 21D | Michael of "Weekend Update" on "S.N.L." (3) | Tracy Gray |
| Tue Jul 23, 2019 | 34A | Michael of "Weekend Update" on "S.N.L." (3) | Kyle Dolan |
| Thu May 30, 2019 | 11A | Revolutionary subject for Banksy | Brandon Koppy |
| Sun Apr 21, 2019 | 72D | "Weekend Update" co-anchor beginning in 2014 | Grant Thackray |
| Sun Mar 31, 2019 | 9D | Narrator of "Evita" | Andrew J. Ries |
| Fri Nov 30, 2018 | 24D | Jost's "Weekend Update" co-anchor | Robyn Weintraub |
| Sun Oct 28, 2018 | 4D | Hero interred in Santa Clara, Cuba | Erik Agard |
| Fri Aug 31, 2018 | 15D | Revolutionary figure (3) | Peter Wentz |
| Fri Aug 24, 2018 | 56D | "Evita" narrator (6) | Roland Huget |
| Thu Aug 2, 2018 | 48D | Revolutionary symbol | Xan Vongsathorn |
| Mon Jul 2, 2018 | 55A | Guerrilla ___ Guevara | Evan Kalish |
| Tue May 22, 2018 | 28A | 2008 Benicio Del Toro title role | Jeff Stillman |
| Sat Apr 21, 2018 | 6D | Marxist from Argentina | Daniel Nierenberg |
| Mon Dec 4, 2017 | 20A | Revolutionary Guevara (10) | Alan Arbesfeld |
| Tue Oct 17, 2017 | 47A | Rebel on many T-shirts | Jeff Chen |
| Sun Jul 9, 2017 | 67A | Subject of the photo "Guerrillero Heroico" | Will Nediger |
| Mon May 23, 2016 | 39D | Guerrilla Guevara (2) | Ori Brian |
| Thu Feb 25, 2016 | 45A | Friend of Fidel (5) | Joel Fagliano |
| Wed Feb 17, 2016 | 37A | "Weekend Update" co-anchor Michael | Kyle Mahowald |
| Sat Jan 9, 2016 | 23A | What's what in Italy? (2) | Jason Flinn |
| Sun Dec 27, 2015 | 71A | Michael of "Saturday Night Live" (2) | Don Gagliardo and Zhouqin Burnikel |
| Mon Dec 14, 2015 | 33D | Revolutionary Guevara (10) | Timothy Polin |
| Wed Oct 21, 2015 | 2D | Physician-turned-revolutionary | Mary Lou Guizzo and Jeff Chen |
| Sun Mar 8, 2015 | 114D | What's that in Italy? (2) | Tom McCoy |
| Fri Feb 20, 2015 | 16A | Motorcyclist who became a rebel | David Woolf |
| Tue Jan 20, 2015 | 45A | "Evita" role (11) | Susan Gelfand |
| Sat Jan 10, 2015 | 23D | Revolutionary figure (3) | Joe Krozel |
| Thu Oct 23, 2014 | 40A | Michael of "Weekend Update" on "S.N.L." (3) | Patrick Blindauer |
| Fri Aug 1, 2014 | 50D | Revolutionary name (4) | Ashton Anderson and James Mulhern |
| Sat Apr 12, 2014 | 12A | Rebel in a beret | Mel Rosen |
| Wed Mar 5, 2014 | 1A | Beret-sporting rebel, familiarly | Evan Birnholz |
| Wed Nov 27, 2013 | 23A | "Evita" character (2) | Jules P. Markey |
| Tue Nov 5, 2013 | 64A | Who said "The revolution is not an apple that falls when it is ripe. You have to make it fall" | Paula Gamache |
| Sun Oct 20, 2013 | 101D | Revolutionary figure (3) | Elizabeth C. Gorski |
| Thu Aug 29, 2013 | 64A | Revolutionary icon (2) | Timothy Polin |
| Thu May 30, 2013 | 36A | Popular dorm poster subject | Julian Lim |
| Sat Feb 2, 2013 | 37A | Figure in a beret | Gareth Bain |
| Thu Sep 20, 2012 | 37A | What's that in Italy? (2) | John R. Conrad |
| Sat Sep 1, 2012 | 63D | Symbol of rebellion on many T-shirts | Tim Croce |
| Thu May 31, 2012 | 15D | "Evita" role (11) | Elizabeth C. Gorski |
| Mon Mar 12, 2012 | 34A | ___ Guevara (9) | Lynn Lempel |
| Wed Feb 29, 2012 | 59D | Tony-winning role for Mandy Patinkin (2) | Kevan Choset |
| Fri Dec 23, 2011 | 39A | "Evita" narrator (6) | Patrick Berry |
| Sat Nov 5, 2011 | 21A | Title role for Omar Sharif or Benicio Del Toro | Kurt Mueller |
| Sun Oct 16, 2011 | 15D | 1969 film with an exclamation point in its title | Joel Fagliano |
| Sun Aug 28, 2011 | 86D | "Evita" narrator (6) | Patrick Berry |
| Mon Jun 13, 2011 | 62A | ___ Guevara (9) | Alex Vratsanos |
| Mon Feb 14, 2011 | 52A | ___ Guevara (9) | Victor Fleming and Lynn Lempel |
| Fri Jan 14, 2011 | 7D | 1969 biopic starring 10-Down | Martin Ashwood-Smith |
| Sun Dec 26, 2010 | 83D | "El ___ vive!" (revolutionary catchphrase) | Darin McDaniel |
| Sun Aug 22, 2010 | 53A | "Evita" narrator (6) | Patrick Berry |
| Wed Jan 6, 2010 | 27D | 2008 title role for Benicio Del Toro | Julian Lim |
| Sat Feb 14, 2009 | 42D | 1969 Omar Sharif title role | Joe Krozel |
| Mon Jun 30, 2008 | 40D | Fighter with Fidel (2) | Lynn Lempel |
| Thu May 1, 2008 | 63A | What: It. | Jim Leeds |
| Tue Apr 22, 2008 | 61D | ___ Guevara (9) | Nancy Salomon |
| Tue Jul 31, 2007 | 37D | Rebel Guevara | Allan E. Parrish |
| Mon Jul 2, 2007 | 7A | Revolutionary Guevara (10) | Peter A. Collins |
| Mon Jun 25, 2007 | 64D | Revolutionary Guevara (10) | Kurt Mengel and Jan-Michele Gianette |
| Tue Feb 27, 2007 | 27D | ___ Guevara (9) | Allan E. Parrish |
| Thu Dec 21, 2006 | 6A | 1969 biopic starring Omar Sharif | Lynn Lempel |
| Wed Aug 23, 2006 | 60D | Comrade of Fidel | Kevan Choset |
| Tue Apr 11, 2006 | 5D | "Evita" role (11) | Lee Glickstein and Nancy Salomon |
| Sun Mar 5, 2006 | 51D | "Evita" narrator (6) | Ashish Madhukar Vengsarkar |
| Sun Sep 4, 2005 | 111D | "Evita" role (11) | Richard Silvestri |
| Sun Mar 20, 2005 | 111D | "Evita" role (11) | Patrick Berry |
| Mon Feb 14, 2005 | 29A | Revolutionary Guevara (10) | Janet R. Bender |
| Sun Feb 13, 2005 | 48D | Italian question starter | Daniel C. Bryant |
| Tue Jan 18, 2005 | 11A | Revolutionary Guevara (10) | Richard Chisholm |
| Sun Dec 19, 2004 | 81D | Subject of "The Motorcycle Diaries" | Frances Hansen (1919-2004) |
| Sun Sep 19, 2004 | 66A | Revolutionary Guevara (10) | Kyle Mahowald |
| Mon Jul 19, 2004 | 53D | Friend of Fidel (5) | Nancy Salomon and Kendall Twigg |
| Thu Jun 17, 2004 | 35A | Noted guerrilla | Robert H. Wolfe |
| Thu May 6, 2004 | 10A | 1969 movie with an exclamation point in its name | Kevan Choset |
| Wed Apr 14, 2004 | 59D | Hero to Fidel | Randolph Ross |
| Sun Jul 20, 2003 | 60D | Compadre of Fidel (3) | Patrick Merrell |
| Sun Jul 13, 2003 | 83D | "Evita" role (11) | Randolph Ross |
| Wed Feb 26, 2003 | 57D | Leader in a beret (2) | Greg Staples |
| Sat Nov 23, 2002 | 10A | 60-Across role | Dana Motley |
| Sun Oct 20, 2002 | 115D | "Evita" narrator (6) | Harvey Estes and Nancy Salomon |
| Wed Jul 31, 2002 | 9D | Compadre of Fidel (3) | Jerry E. Rosman |
| Thu May 2, 2002 | 7D | "Evita" role (11) | Dave and Diane Epperson |
| Tue Apr 30, 2002 | 24A | Amigo of Fidel (2) | John F. Hughes |
| Wed Oct 24, 2001 | 23A | Friend of Fidel (5) | Sarah Keller |
| Sun Oct 14, 2001 | 78D | What's that, Carlo? | Elizabeth C. Gorski |
| Wed Jul 4, 2001 | 10A | Leader in a beret (2) | John Beck |
| Wed Jun 6, 2001 | 23A | "Waltz for Eva and ___" (show tune) | Richard Silvestri |
| Wed May 23, 2001 | 5A | "Evita" role (11) | Alan Arbesfeld |
| Wed Apr 11, 2001 | 53A | "Evita" role (11) | Brendan Emmett Quigley |
| Tue Nov 28, 2000 | 66D | Friend of Fidel (5) | Richard Hughes |
| Sat Nov 4, 2000 | 32D | Cuban Revolution name | Rich Norris |
| Sat Oct 28, 2000 | 4D | "Voi ___ sapete" (Mozart aria) | Elizabeth C. Gorski |
| Thu Sep 28, 2000 | 36A | 1969 movie starring Omar Sharif | Frances Hansen |
| Sat Aug 5, 2000 | 48A | "El ___" (1998 documentary) | Manny Nosowsky |
| Thu May 25, 2000 | 40A | "Evita" role (11) | Elizabeth C. Gorski |
| Sun Jan 30, 2000 | 31A | Fourth Spanish letter (2) | Peter Gordon |
| Sun Oct 31, 1999 | 111D | Bearded revolutionary (2) | Frank A. Longo |
| Sat Jul 3, 1999 | 30A | He swore fidelity to Fidel | David J. Kahn |
| Tue Jun 15, 1999 | 51A | "Evita" character (2) | Stephanie Spadaccini |
| Thu Apr 8, 1999 | 33D | 29-Down role | David J. Kahn |
| Sun Jan 31, 1999 | 42D | With 83-Down, "new socialist man" advocate | Manny Nosowsky |
| Wed Jan 27, 1999 | 13D | Fighter with Fidel (2) | Leslie Billig |
| Thu Sep 3, 1998 | 23A | "Evita" role (11) | Manny Nosowsky |
| Sun May 3, 1998 | 56D | Revolutionary name (4) | Brendan Emmett Quigley |
| Mon Mar 23, 1998 | 59D | Cuban hero Guevara | Randall J. Hartman |
| Mon Feb 23, 1998 | 40D | Guerrilla Guevara (2) | Mark Danna |
| Tue Feb 3, 1998 | 57D | ___ Guevara (9) | Nancy Salomon |
| Sun Feb 1, 1998 | 81D | He helped topple Batista | Merl Reagle |
| Sun Nov 9, 1997 | 33A | His real name was Ernesto | Rich Norris |
| Thu Jul 31, 1997 | 47A | Revolutionary nickname | Trip Payne |
| Mon Apr 14, 1997 | 44A | Senor Guevara (2) | Stephanie Spadaccini |
| Sat Apr 12, 1997 | 25A | Antonio Banderas, in "Evita" | Bob Klahn |
| Sun Mar 2, 1997 | 31D | Antonio's role in "Evita" | Harvey Estes |
| Sun Dec 1, 1996 | 52A | Lloyd Webber musical role | D. J. Kahn |
| Tue Oct 1, 1996 | 25A | Compadre of Fidel (3) | R. J. Hartman |
| Sun Aug 18, 1996 | 42D | Revolutionary name (4) | F. and L. Sabin |
| Mon Feb 26, 1996 | 40A | ___Guevara (9) | N. Steinberg |
| Thu Feb 22, 1996 | 31A | Lieutenant of Fidel, once | C. Deodene |
| Tue Dec 19, 1995 | 53D | ___ Guevara (9) | Marie Heller |
| Mon Oct 23, 1995 | 41D | Revolutionary Guevara (10) | Sidney L. Robbins |
| Sun Oct 22, 1995 | 114A | Legendary Latin hero | Matt Gaffney |
| Sun Aug 13, 1995 | 21A | Revolutionary name (4) | Nancy Salomon |
| Tue May 16, 1995 | 6D | Onetime Fidel ally | David J. Kahn |
| Fri May 12, 1995 | 20A | Señor Guevara | Rich Norris |
| Sun Feb 5, 1995 | 71A | Bearded revolutionary (2) | Frank A. Longo |
| Fri Jan 20, 1995 | 31A | Fourth Spanish letter (2) | Manny Nosowsky |
| Sun Dec 11, 1994 | 98A | 1969 Broadway hit (2) | Wayne Robert Williams |
| Wed Dec 7, 1994 | 31A | ___ Guevara (9) | Chet Currier |
| Fri Sep 30, 1994 | 55D | 1969 Broadway hit (2) | Matt Gaffney |
| Mon May 23, 1994 | 50A | Senor Guevara (2) | Jonathan Schmatzbach |
| Fri May 20, 1994 | 62D | Amigo of Fidel (2) | Manny Nosowsky |
| Sun Apr 17, 1994 | 73D | Friend of Fidel (5) | R. M. Hopkins |
| Sun Apr 10, 1994 | 37A | 1969 Omar Sharif role | Trip Payne |
| Fri Mar 18, 1994 | 4D | Ernesto Guevara, familiarly | Mark Diehl |