Fans of the
Times crossword have kept track of a number of records and interesting puzzles (primarily from among those published in Shortz's tenure), including those below. (All puzzles published from November 21, 1993, on are available to online subscribers to the
Times crossword.) in a Sunday puzzle: 117 words on November 2, 2025, by Rafael Musa. • Most words in a daily puzzle: 86 words on Tuesday, December 23, 2008, by Joe Krozel; in a 21x21 Sunday puzzle: 150 words, on June 26, 1994, by Nancy Nicholson Joline and on November 21, 1993, by Peter Gordon (the first Sunday puzzle edited by Will Shortz). • Fewest black squares (in a daily 15x15 puzzle): 17 blocks, on Friday, July 27, 2012, by Joe Krozel. • Most prolific author:
Manny Nosowsky is the crossword constructor who has been published most frequently in the Times under Shortz, with 241 puzzles (254 including pre-Shortz-era puzzles, published before 1993), although others may have written more puzzles than that under prior editors. The record for most Sunday puzzles is held by Jack Luzzatto, with 119 (including two written under pseudonyms); former editor Eugene T. Maleska wrote 110 himself, including 8 under other names. • Oldest constructor:
Bernice Gordon was 100 on August 11, 2014, when her final
Times crossword was published. (She died in 2015 at the age of 101.) Gordon published over 150 crosswords in the
Times since her first puzzle was published by Margaret Farrar in 1952. • Greatest difference in ages between two constructors of a single puzzle: 83, a puzzle by David Steinberg (age 16) and Bernice Gordon (age 99) with the theme AGE DIFFERENCE. • 15-letter-word stacks: On December 29, 2012, Joe Krozel stacked five 15-letter entries, something never before or since achieved. Krozel, Martin Ashwood-Smith, George Barany and Erik Agard have stacked four 15-letter entries in a puzzle. Since 2010, Krozel, Ashwood-Smith, Kevin G. Der, and Jason Flinn have stacked two sets of four 15-letter entries in a puzzle. • Lowest word count for a debut puzzle: 62 words, on Saturday, June 1, 2019, by Ari Richter. A few crosswords have achieved recognition beyond the community of crossword solvers. Perhaps the most famous is the November 5, 1996, puzzle by
Jeremiah Farrell, published on the day of the
U.S. presidential election, which has been featured in the movie
Wordplay and the book
The Crossword Obsession by Coral Amende, as well as discussed by Peter Jennings on ABC News, featured on CNN, and elsewhere. The two leading candidates that year were
Bill Clinton and
Bob Dole; in Farrell's puzzle, one of the long clue/answer combinations read [Title for 39-Across next year] MISTER PRESIDENT. The remarkable feature of the puzzle is that 39-Across could be answered either CLINTON or BOB DOLE, and all the Down clues and answers that crossed it would work either way (e.g., [Black Halloween animal] could be either BAT or CAT depending on which answer you filled in at 39-Across; similarly [French 101 word] could equal LUI or OUI, etc.). In another notable
Times crossword, 27-year-old Bill Gottlieb proposed to his girlfriend, Emily Mindel, via the crossword puzzle of January 7, 1998, written by noted crossword constructor Bob Klahn. The answer to 14-Across, [Microsoft chief, to some] was BILLG, also Gottlieb's name and last initial. 20-Across, [1729 Jonathan Swift pamphlet], was A MODEST PROPOSAL. And 56-Across, [1992 Paula Abdul hit], was WILL YOU MARRY ME. Gottlieb's girlfriend said yes. The puzzle attracted attention in the AP, an article in the
Times itself, and elsewhere. Shortz described the President's work as "laugh out loud" and noted that he as editor changed very little of Clinton's clues, which featured more wordplay than found in a standard puzzle. The
Times crossword of Thursday, April 2, 2009, by
Brendan Emmett Quigley, featured theme answers that all ran the gamut of
movie ratings—beginning with the kid-friendly "G" and finishing with
adults-only "X" (now replaced by the less crossword-friendly "
NC-17"). The seven theme entries were
GARY GYGAX,
GRAND PRIX,
GORE-TEX,
GAG REFLEX,
GUMMO MARX, GASOLINE TAX, and
GENERATION X. In addition, the puzzle contained the clues/answers of
[Weird Al Yankovic's "__ on Jeopardy"] for
I LOST and ["I'll take
New York Times crossword for $200, __"] for
ALEX. What made the puzzle notable is that the prior night's episode of the US television show
Jeopardy! featured video clues of Will Shortz for five of the theme answers (all but GARY GYGAX and GENERATION X) which the contestants attempted to answer during the course of the show. On April 19, 2026, the
Times published a crossword that was unsolvable, the first in its history. The crossword in question initially included a missing 5-across clue before it was corrected in the digital edition. == Controversies ==