Natan Last: Who Has Time for Crosswords? (Not Joyce Carol Oates)

Crossword constructor Natan Last joins Ira for a conversation about taste, culture, and the surprising power of play. They discuss how crossword puzzles shape the cultural canon, why every clue has a point of view, and what it means to create work that reflects your own voice. Natan also revisits the moment he made Ira a clue in The New York Times crossword. Plus, they get into AI, the COVID game boom, and why making a crossword is a lot like creating the perfect mixtape! 00:00 Intro to Madonna, Politics & the Internet This Week 04:39 How Natan Last Fell in Love with Crosswords 06:52 Building a New York Times Crossword at Just 16 08:18 How Crossword Puzzles Became Pop Culture 12:20 Why Modern Crosswords Look So Different Today 17:10 From Intern to Protégé: Learning From Will Shortz 21:11 The Day Ira Madison III Became a Crossword Clue in the New York Times 23:50 How Crossword Constructors Develop Their Own Voice 27:16 New York Times vs. The New Yorker Crosswords 30:04 Can a Crossword Puzzle Be Political? 32:29 Nabokov, Literature & Why Crosswords Matter 35:24 The Wild History of America's Crossword Craze 42:01 How Do You Get More People Solving Crosswords? 44:29 Inside Will Shortz's Crossword Workshop 48:24 Can AI Actually Make Great Crosswords? 53:21 Toni Morrison, Longhand Writing & Creativity 58:42 Lil Wayne, MF DOOM & the Genius of Wordplay 1:02:21 The Greatest Crossword Clues Ever Written — FOLLOW THE SHOW 🎧 Listen on Apple Podcasts: https://podcasts.apple.com/us/podcast... 🎧 Listen on Spotify: https://open.spotify.com/show/033piOi... 🎧 Listen on Acast: https://shows.acast.com/feedback-with... 📺 Subscribe on YouTube:    / @feedbackwithira   — FOLLOW NATAN LAST Website: https://natanlast.com/ Instagram:   / natanlast   — FOLLOW IRA MADISON III Instagram:   / irathethird   Threads: https://www.threads.com/@irathethird TikTok:   / irathethird   Substack: https://iramadison.substack.com/ — CREDITS Hosted by: Ira Madison III Produced by: Taylor Williamson, Melia Agudelo, Eve Bishop, Alyia Yates Grau, Paloma Moreno Jiménez, and Gianna Palmer. Executive Producers: Jenny Kaplan and Emily Rudder