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| Date | Grid | Clue | Author |
|---|---|---|---|
| Saturday, April 6, 2013 | 5D | "Witchcraft" singer | Michael Wiesenberg |
| Sunday, July 3, 2011 | 100D | Artist whose name is an anagram of "artisan" | Pete Muller |
| Wednesday, October 6, 2010 | 28D | Singer honored on a 2008 U.S. postage stamp | Ian Livengood |
| Sunday, January 31, 2010 | 1A | Ol' Blue Eyes | Tony Orbach and Andrea Carla Michaels |
| Saturday, January 24, 2009 | 40D | Sands part-owner, once | Mark Diehl |
| Friday, October 26, 2007 | 25D | 1963 Academy Awards host | David Quarfoot |
| Thursday, August 23, 2007 | 43D | Singer who founded Reprise Records | Joe Krozel |
| Friday, February 9, 2007 | 38A | Subject of the biography "All or Nothing at All" | Eric Berlin |
| Thursday, July 21, 2005 | 64A | His first #1 song was "All or Nothing at All" | Patrick Blindauer |
| Thursday, June 2, 2005 | 4A | Noted Tommy Dorsey Orchestra alumnus | Levi Denham |
| Wednesday, May 25, 2005 | 11D | Bobbysoxer idol | Nancy Salomon |
| Friday, April 9, 2004 | 1D | Founder of Reprise Records | Bob Peoples |
| Friday, April 11, 2003 | 7D | "The Manchurian Candidate" actor | Elizabeth C. Gorski |
| Sunday, January 5, 2003 | 91D | "On the Town" actor | Elizabeth C. Gorski |
| Tuesday, July 16, 2002 | 46D | Original "Ocean's Eleven" star | Ed Early |
| Sunday, March 3, 2002 | 59D | "On the Town" performer | Elizabeth C. Gorski |
| Sunday, May 13, 2001 | 48D | Oscar winner of 1953 | Nancy Nicholson Joline |
| Monday, December 18, 2000 | 50A | Crooner Frank | Nancy Kavanaugh |
| Friday, May 12, 2000 | 1D | "The Man With the Golden Arm" star, 1955 | Manny Nosowsky |
| Monday, August 17, 1998 | 46A | Late, great crooner | Gregory E. Paul |
| Tuesday, October 18, 1994 | 14A | "Strangers in the Night" singer | Harvey Estes |
| Wednesday, February 2, 1994 | 30A | "Hey! Jealous Lover" singer | Robert Katz |
2 results for SINATRA from Variety puzzles.
| Date | Type | Grid | Clue | Author |
|---|---|---|---|---|
| June 26, 2011 | diagramless | 48D | Rat Pack leader | Fred Piscop |
| February 15, 2009 | acrostic | D | Entertainer whose epitaph reads "The best is yet to come" | Emily Cox and Henry Rathvon |
8 results for SINATRA from older pre-Shortz puzzles.
| Date | Grid | Clue | Author | Editor |
|---|---|---|---|---|
| Saturday, August 22, 1992 | 8A | Oscar winner of 1953 | Richard Silvestri | Maleska |
| Thursday, February 27, 1992 | 37D | "Rat Pack" leader | Jeff Herrington | Maleska |
| Wednesday, December 12, 1990 | 20A | Singer born Dec. 12, 1915 | Richard Silvestri | Maleska |
| Sunday, August 26, 1990 | 61A | Anagram for artisan | Norma Steinberg | Maleska |
| Sunday, August 24, 1986 | 102D | Pride of Hoboken | Arnold Moss | Maleska |
| Wednesday, December 12, 1984 | 49A | "The Voice" | John M. Samson | Maleska |
| Tuesday, November 20, 1984 | 54A | Ol' Blue Eyes | Leslie | Maleska |
| Saturday, July 30, 1983 | 46A | He sang with James | Julian Ochrymowych | Maleska |