Podcast Summary:

All Of It with WNYC

Episode: The Past, Present, and Future of the Crossword Puzzle

Host: David Fuerst (in for Alison Stewart)
Date: December 17, 2025
Guest: Natan Last, crossword constructor, author of Across the: The Past, Present and Future of the Crossword Puzzle

Episode Overview

This episode delves into the enduring appeal, cultural significance, and evolution of the crossword puzzle. David Fuerst hosts Natan Last, longtime puzzle constructor and author, for an engaging discussion about crosswords' origins, their changing place in American life, the impact of technology and artificial intelligence, and the surprising emotional and communal benefits these word games bring.

Key Discussion Points & Insights

1. The Magnetic Pull and Memory of Crosswords

• Natan's Personal Entry:
  • Natan recounts discovering the unique "afterglow" of problem-solving with a crossword as a teen, when answers arrived on his "neurological backburner" after a break ([01:27]).
    • Quote:

      "I remember the sensation of I didn't know the answers, you know, five minutes ago, but now I do." – Natan Last [01:58]

2. Historical Origins and Early Pushback

• Arthur Wynne and the First Crossword:
  • The first crossword appeared in the New York World in 1913, filling extra space for a holiday issue ([02:29]).
  • Overnight popularity was paired with backlash, with critics decrying puzzles as "a waste of time" and even libraries “blotting them out” ([02:57]).
    • Quote:

      "People named this disease Crossroaditis. They were so aghast at how people were using their newfound leisure time." – Natan Last [03:20]

  • The crossword was seen as symbolic of America's new, often-criticized leisure culture following WWI.

3. Language, Pop Culture, and Crosswordese

• Evolving Lexicon:
  • Before famed editor Will Shortz, crossword clues were often obscure or dated; for example, "Oreo" was clued as a Greek prefix, not a cookie, until 1993 ([04:29]).
  • Constructors today reimagine answers, shifting clues to match contemporary language and cultural reference points.
    • Quote:

      "Crossword constructors, especially younger ones, are interested in sort of reformulating little morsels of language... Words are constantly evolving and the crossword can kind of both track it, but also have a hand in shaping it." – Natan Last [05:05]

4. Mental Benefits & Pattern Recognition

• Crossword-solving encouraged broad but often odd vocabularies and nurtured pattern recognition skills more than simple trivia recall ([05:43]).
  • Quote:

    "Really high caliber solvers tend to say that when you get better, you start to solve the grid more than you solve the clues." – Natan Last [06:06]

5. The Digital Age: Software, AI, and the Puzzle-Maker's Toolbox

• Theme design, grid construction, and clue-writing define the constructor's job ([07:10]).
• Software makes grid-building easier, even inspiring more complex themes by scripting searches for patterned phrases ([07:44]).
  • Example: using scripts to find phrases with virtually identical or repeating letters, which is hard to do manually.
• AI Concerns: While computers are helpful, the greater threat lies in publishers exploiting existing puzzles to generate content using AI, raising copyright and labor concerns ([08:46]).
  • Quote:

    "For now, it's a matter of not letting, you know, big publishers and other organizations use past puzzles in order to generate AI puzzles. That's the battle... That's stealing." – Natan Last [09:13]

6. Legends of the Game: Will Shortz & Margaret Farrar

• Will Shortz: Revolutionized the New York Times puzzle in 1993 by broadening its content to include pop culture, humor, and modern references ([10:07]).
  • The puzzle shifted from an academic, Latin-oriented rigor to "Technicolor," making it fun and relevant.
  • Quote:

    "...the puzzle was all of a sudden brimming with the sort of things that all of us encounter in real life. It also started to be a lot funnier." – Natan Last [10:16]

  • Margaret Farrar: As the Times' first crossword editor, advocated adding the puzzle during WWII (to distract the home front), and standardized many modern crossword conventions ([11:25]).
    • Example: grid symmetry, avoiding two-letter words, discouraging obscurities ([12:10]).
    • Quote:

      "You can't think of your troubles, she said, while solving a crossword." – Natan Last, retelling Farrar’s words [11:51]

7. Tactility and Changing Habits

• Listeners reminisce about doing crosswords in pen as a badge of honor; Natan himself prefers paper for its tactile pleasure ([13:17]).

8. Healing Power and Psychology of Puzzling

• Listener Story: Steven from Montclair shares that crosswords helped him recover neural function after Lyme disease ([13:38]).
  • Quote:

    "...doing crosswords was a really important part of kind of rebuilding my neural pathways." – Steven, caller [13:49]

• Benefits During Crisis: Many people (including COVID-19 lockdown) used puzzles to rebuild focus and attention ([14:44]–[15:03]).

9. Social Connection and Tradition

• Crosswords foster both deep opinions and lively debate in user communities; they have become increasingly interactive thanks to digital platforms and comment sections ([17:24]).
  • Quote:

    "They probably always had strong opinions about it. It's just much more in our face." – Natan Last [18:35]

• Collaboration and Relationships: Listeners describe solving puzzles with partners, children, and across generations—including stories of romance, family bonding, and accessibility for the visually impaired ([19:12]–[20:43]).
  • Quote:

    "The puzzle is thought of as this individual, solitary pursuit. But of course it's bringing people together all the time." – Natan Last [19:50]

10. Crosswords as Progress

• Natan argues that while social change starts “on the streets,” crosswords can drive smaller forms of progress by correcting historical records and challenging biases ([15:38]).
  • Example: The shifting clues for "MAU MAU" reflect broader societal changes in how historical events are interpreted ([16:20]).
  • Quote:

    "...the crossword can play a small role in correcting the record." – Natan Last [17:00]

Notable Quotes & Moments (by Timestamp)

• [01:58] – “I remember the sensation of I didn't know the answers, you know, five minutes ago, but now I do.” — Natan Last
• [03:20] – “People named this disease Crossroaditis. They were so aghast at how people were using their newfound leisure time.” — Natan Last
• [05:05] – “Crossword constructors...are interested in reformulating little morsels of language. Words are constantly evolving, and the crossword can...both track it, but also have a hand in shaping it.” — Natan Last
• [06:06] – “When you get better, you start to solve the grid more than you solve the clues.” — Natan Last
• [09:13] – “For now, it's a matter of not letting, you know, big publishers and...organizations use past puzzles in order to generate AI puzzles. That's the battle...That's stealing.” — Natan Last
• [10:16] – “The puzzle was all of a sudden brimming with the sort of things that all of us encounter in real life. It also started to be a lot funnier.” — Natan Last
• [11:51] – “You can't think of your troubles, she said, while solving a crossword.” — Natan Last (on Margaret Farrar)
• [13:49] – “Doing crosswords was a really important part of kind of rebuilding my neural pathways.” — Steven (caller)
• [17:00] – “...the crossword can play a small role in correcting the record.” — Natan Last
• [19:50] – “The puzzle is thought of as this individual, solitary pursuit. But of course, it's bringing people together all the time.” — Natan Last

Timestamps for Major Segments

• [00:08] – Introduction and the rising popularity of crosswords
• [01:27] – Natan’s personal “crossword moment”
• [02:22] – History of crosswords and backlash
• [04:29] – Crossword clues and cultural resonance
• [05:43] – Mental benefits and odd vocabularies
• [07:10] – Puzzle construction, software, and AI
• [10:07] – The Will Shortz legacy
• [11:25] – Margaret Farrar and WWII
• [13:17] – Old-school solving in pen versus digital
• [13:38] – Listener story: Crosswords and neural recovery
• [15:38] – Can crosswords be a force for social progress?
• [17:24] – Deep emotions and puzzle culture debates
• [19:12] – Relationships and cooperative solving

Tone, Style, and Takeaway

The conversation is lively, warm, and filled with both nostalgia and practical observations. The show balances technical insights with human stories, demonstrating that crosswords are more than just a pastime—they are a living, evolving facet of culture that fosters community, learning, and even healing. Natan Last’s enthusiasm and storytelling, paired with passionate listener anecdotes, paint a full picture of why crosswords endure.

Recommended for:
Anyone interested in puzzles, language, cultural evolution, and communal traditions—or those seeking inspiration from everyday things that quietly transform our lives.