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

04:39 Discovering Crossword Construction with Natan Last

06:52 Publishing a New York Times Crossword at Sixteen

12:20 How Crosswords Changed With Pop Culture

17:10 Editors, Constructors & Finding Your Voice

21:11 Ira Becoming a Crossword Clue

27:16 Writing for The New York Times vs. The New Yorker

30:04 Editorial Choices and the Politics of Clues

35:35 The Surprising History of the Crossword Craze

42:01 Building the Next Generation of Crossword Solvers

44:29 Learning From Will Shortz

48:24 AI, Authorship & the Future of Crosswords

53:21 Writing Longhand, Toni Morrison & Creative Process

58:42 Rap, Poetry & the Joy of Wordplay

1:02:21 Favorite Crossword Clues

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This week on Feedback, Ira sits down with Vanity Fair contributing editor and author Anna Peele to unpack her new book, Enter the Villa, and dissect the cultural phenomenon of Love Island. Together, they break down the show's psychological impact and question if a show this consuming can be made without destroying its stars' lives. They also discuss the art of the celebrity profile, including Anna's infamous 2015 Miles Teller interview that terrified a generation of publicists.

00:00 Welcome to Feedback with Ira Madison III

04:50 From Vanity Fair Feature to Writing 'Enter the Villa'

06:51 Ariana Madix, Producer Manipulation, and Islanders' Well-being

07:49 The Psychological Impact of Love Island

09:22 Racial Diversity Across Bravo's Reality Shows

12:20 Auditioning and Diverse Casting in the Villa

14:49 Love Island Fandom Backlash, Subreddits, and Online Discourse

17:54 Which Love Islander Would Anna Cast in 'Cats'?

21:11 PPG's Response to Anna’s Book

23:36 Dissecting Rob’s Gameplay on Love Island and Traitors

26:08 Real Housewives of Beverly Hills and the Future of Dorit Kemsley

30:16 Ira Was Blindsided on Fox’s Reality Competition, 'The Floor'

35:10 Reality Show Set Rules and Misconduct

40:48 The Changing Stakes of the Contemporary Celebrity Profile

41:47 Revisiting the Infamous 2015 Miles Teller Esquire Interview

44:02 Profiling Charli XCX and the Brat Era

51:11 Securing the Elusive Bianca Censori Interview

55:21 The Nostalgia and Identity of Classic Men's Magazines

01:02:22 Nancy Jo Sales’ Legendary Leonardo DiCaprio Profile

01:10:03 The Real Housewives Ultimate Girls Trip: Roaring 20th

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This week, Ira is joined by theatre-obsessed culture critics Soraya McDonald and Juan Ramírez for a post-mortem conversation about the Tonys and the recently concluded theatre season in New York. Juan is the Chief Critic at Theatrely and Soraya was a finalist for the Pulitzer Prize in Criticism. The three share some bourbon and pull back the curtain on everything Broadway and Off-Broadway. They discuss what makes colorblind casting work (and when it falls flat) and why Henrik Ibsen was a gaggy queen. Pour yourself a drink before you watch this recap… and get ready to be gagged a few times.

00:00 Welcome to Feedback with Ira Madison III

02:17 Critics Soraya McDonald and Juan Ramírez on Theater

03:38 Award Seasons, Broadway Revivals, and Artistic Merits

09:21 The Evolving Conversation Around Colorblind Casting

14:49 Identity, Representation, and the Commercial Stage

25:46 Stage-to-Screen Adaptations and Modern Audiences

28:42 Artistic Risks, Budget Constraints, and Regional Ecosystems

33:16 Classic Playwrights, Tennessee Williams, and Henrik Ibsen

37:57 The Public Theater’s Romeo and Juliet as Border-Crossed Lovers

44:48 Pink, Live Hosting and The Tony Awards

47:30 Jukebox Musicals, Missy Elliot, and Pop Music Icons

49:40 Vocal Mastery, Carmen Hip-hopera, and Historic Opera

53:41 Closing Reflections on Dream Revivals and Nightmare Revivals

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