[6] The larger Sunday crossword, which appears in The New York Times Magazine, is an icon in American culture; it is typically intended to be a "Wednesday or Thursday" in difficulty.

[12] The motivating impulse for the Times to finally run the puzzle (which took over 20 years even though its publisher, Arthur Hays Sulzberger, was a longtime crossword fan) appears to have been the bombing of Pearl Harbor; in a memo dated December 18, 1941, an editor conceded that the puzzle deserved space in the paper, considering what was happening elsewhere in the world and that readers might need something to occupy themselves during blackouts.

[16][17] There have also been two interim editors of the puzzle: Mel Taub from September 6 to November 20, 1993, after Maleska's death; and Joel Fagliano, from March to December 2024, while Shortz was on medical leave.

Many celebrities and public figures have publicly proclaimed their liking for the puzzle, including opera singer Beverly Sills,[11] author Norman Mailer,[20] baseball pitcher Mike Mussina,[21] former President Bill Clinton,[22] conductor Leonard Bernstein,[11] TV host Jon Stewart,[21] actress Gillian Jacobs,[23] and music duo the Indigo Girls.

Various other forms of merchandise featuring the puzzle have been created, including dedicated electronic crossword handhelds that just contain Times crosswords, and a variety of Times crossword-themed memorabilia, including cookie jars, baseballs, cufflinks, plates, coasters, and mousepads.

This is often some sort of connection between at least three long across answers, such as similar types of puns, added letters, or hidden synonyms.

[26] The Friday and Saturday puzzles, the most difficult, are almost always themeless and "wide open", with fewer black squares and more long words.

[9] Given the Times's reputation as a paper for a literate, well-read, and somewhat arty audience, puzzles frequently reference works of literature, art, or classical music, as well as modern TV, movies, or other touchstones of popular culture.

The Mini is popular, but has also been criticized, sometimes harshly, for its comparative simplicity—with one review of the game in Slate magazine titled "Utter Disgrace to the NYT Crossword Brand".

[25] 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.

[22][57] 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.

[22][57] Clinton made his print constructing debut on Friday, May 12, 2017, collaborating with Vic Fleming on one of the co-constructed puzzles celebrating the crossword's 75th Anniversary.

[58] The Times crossword of Thursday, April 2, 2009, by Brendan Emmett Quigley,[59] 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.

Major crosswords like those in the Times have historically been created and edited primarily by older white men.