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Feedback with Ira Madison III
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
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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11. The Incel-ification of the Internet with Josh Lora
01:10:29||Season 1, Ep. 11This week, Ira sits down with writer, cultural critic, and TikTok commentator Josh Lora (@tellthebeees) to unpack the cultural forces shaping what we watch, read, and obsess over online. They get into Christopher Nolan’s The Odyssey, the internet’s growing fixation on masculinity, and why TikTok has turned beauty, loneliness, and dating into a warped competition. Along the way, they debate the state of BookTok, the death of counterculture, and whether reality TV needs a little more mess. Plus, Josh explains the Harry Jowsey lore and why you absolutely do not need to watch Let’s Marry Harry.00:00 Ira Madison III Introduces the Episode04:21 Josh Lora Joins Ira: Christopher Nolan & The Odyssey07:40 The Odyssey, Identity & Representation12:05 Christopher Nolan’s Fascination With Masculinity20:45 Masculinity, Guilt & the “Great Man”24:29 Interstellar, Spider-Man & Male Loneliness32:29 TikTok, Beauty Standards & Online Culture41:09 Daria, Punk & the Death of Counterculture46:55 Celebrity Fandom & the Rise of Stan Culture52:58 BookTok, Reading Culture & DNFing Books56:06 Why Internet Culture Is Getting Darker01:06:41 Reality TV, Netflix & the Death of the Reality Star
10. Is Fan Culture Breaking Bravo? with Gibson Johns
01:17:56||Season 1, Ep. 10This week, Ira sits down with entertainment journalist and Bravo expert Gibson Johns to unpack how covering The Real Housewives and the broader Bravo world evolved from a guilty pleasure to a full-blown media ecosystem. They get into the blurry line between commentator and fan, the Bravo fan impact, and whether reality stars are performing for podcasts and social media as much as they are for the cameras. Along the way, they revisit unforgettable Housewives moments, recall a silly BravoCon confrontation, and hear why Gibson is all in on Love Thy Naders. 0:00 Nene Leakes Is Back: Ultimate Girls Trip: Roaring 20th Review8:50 Gibson Johns Joins the Show10:45 How Gibson Went From Bravo fan to Bravo Journalist 15:29 Critic or Interviewer? Where Gibson Fits In21:50 Andy Cohen's Soft Spots + Caller on Janet & Jason 28:09 Fan Hypocrisy & Has Feedback Gotten Too Powerful?33:23 Constructive Criticism & Performing for the Discourse38:50 Franchise Identity & When a Show Becomes "About the Show"44:41 Hulu's New Reality Shows47:53 Threads Discourse Has Gone Feral50:12 Ira's Apartment Fire Cameo on RHONY: In the City52:27 Gibson's Coverage of the Osefo Drama55:43 Caller: Kelly Bensimon & the Carl Radke Question59:47 Ex-Housewives Spinoffs & Social Capital1:04:39 The Men of Southern Charm1:08:34 Caller: Who Is Rhode Island's Villain?1:12:05 Rapid Fire: Bravo Superlatives1:14:35 Lindsay Hubbard on Threads, Jules & Closing Bits
9. Ciao Amore! You Are Not On the List with Connie Fleming and Lina Bradford
01:21:19||Season 1, Ep. 9New York nightlife isn't dead—you just haven't talked to Connie Fleming and Lina Bradford. The nightlife legends join Ira to swap stories about Madonna's Club Confessions, the golden age of MTV, drag's evolution into performance art, Fire Island, club etiquette, and the music that keeps the dance floor alive. Plus, they settle some nightlife debates—including the right time to leave the afters.0:00 – Intro6:04 – Madonna's Club Confessions NYC10:05 – Connie Fleming: Working NYC's Legendary Club Doors14:21 – The Art of Curating the Perfect Nightlife Crowd17:32 – Drug Culture in the Clubs21:05 – Boy Bar, Drag, Fashion & NYC Performance Art26:13 – Before TikTok: The Lost History of Club Documentarians29:20 – Fighting for LGBTQ Rights Then—and Now32:21 – When Queer Life Moved From the Dark to the Light39:46 – Fire Island, Inclusion & Finding Community47:42 – Listener Call: Biggest Misconceptions about Connie and Lina53:52 – The Music That Still Moves Them58:11 – Connie's First Night at Basement1:00:54 – Are Phones Ruining the Club?1:04:20 – Connie and Lina's Friendship Story1:06:32 – Social Anxiety & Club Etiquette 1:10:13 – Listener Call: When Should You Leave the Afters?
8. Don’t Call Me Mar with Deidre Hall
50:46||Season 1, Ep. 8As a birthday treat to himself, Ira lands one of his dream interviews: A conversation with the iconic Deidre Hall, longtime star of Days of Our Lives. In celebration of 50 years since beginning her tenure as Days’ Dr. Marlena Evans, Deidre digs into all things daytime television, from her many on-screen deaths and revivals, her turn on Hacks, to everything you ever needed to know about finding your best lighting in every photo. Plus, Ira stuns Deidre with his seemingly unending recall for Days’ multitude of plot lines.00:00 Welcome to Feedback with Ira Madison III01:02 Becoming Marlena Evans and 50 Years on Days of Our Lives05:17 Life as a Soap Actor06:36 Working with Writers and Creating Iconic Storylines09:11 Her Twin Sister's Unexpected Soap Opera Career12:04 Soap Deaths, Fan Outrage and Bringing Characters Back15:16 Favorite Storylines: Possession and The Salem Stalker25:13 How Budget Cuts Changed Days of Our Lives27:39 Celebrity Fans and Connecting with Viewers31:18 Daytime TV's Legacy34:16 Ensemble Storytelling, Favorite Castmates, and John and Marlena40:12 Rivalries, Friendships, and Playing Marlena Today43:09 Acting Advice and Guest Starring on Hacks45:45 Future Crossovers, Dream Roles, and What's Next47:11 Why Marlena Will Always Be "Doc"
7. We Miss Magazines with Chrissy Rutherford & John Villa
01:10:14||Season 1, Ep. 7This week on Feedback, Ira sits down with former Harper's Bazaar editor Chrissy Rutherford and fashion commentator John Villa to break down what's happening in the fashion streets. From the magazine covers that still make them stop and buy to why celebrity style feels increasingly uninspired, they unpack the trends, tastemakers, and internet personalities shaping fashion today. Plus, they get into Timothée Chalamet, newsletters, Sex and the City, and why, if you want to make it in fashion, you have to go outside.00:00 The Odyssey and Nolan's Greatest Hits04:47 Summer Time Do's and Don'ts with Chrissy and John10:07 Shein, 7 Jeans, and Every Brand in Between16:57 Magazines vs. Influencers22:25 Magazine Editors & Iconic Covers31:44 Queer Fashion & Heated Rivalry37:01 Press Tours, Timothée Chalamet & Celebrity Fashion47:01 The Reality of Celebrity Styling50:15 Influencer Culture vs. The Fashion Industry59:04 FWD JOY, Newsletters & Building a Brand01:02:46 Knicks Jerseys... It's Still That Deep01:06:48 Carrie Bradshaw & Knowing Your References
5. Anna Peele: Can You Make Love Island Without Destroying Lives?
01:10:26||Season 1, Ep. 5This 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 III04:50 From Vanity Fair Feature to Writing 'Enter the Villa'06:51 Ariana Madix, Producer Manipulation, and Islanders' Well-being07:49 The Psychological Impact of Love Island09:22 Racial Diversity Across Bravo's Reality Shows12:20 Auditioning and Diverse Casting in the Villa14:49 Love Island Fandom Backlash, Subreddits, and Online Discourse17:54 Which Love Islander Would Anna Cast in 'Cats'?21:11 PPG's Response to Anna’s Book23:36 Dissecting Rob’s Gameplay on Love Island and Traitors26:08 Real Housewives of Beverly Hills and the Future of Dorit Kemsley30:16 Ira Was Blindsided on Fox’s Reality Competition, 'The Floor'35:10 Reality Show Set Rules and Misconduct40:48 The Changing Stakes of the Contemporary Celebrity Profile41:47 Revisiting the Infamous 2015 Miles Teller Esquire Interview44:02 Profiling Charli XCX and the Brat Era51:11 Securing the Elusive Bianca Censori Interview55:21 The Nostalgia and Identity of Classic Men's Magazines01:02:22 Nancy Jo Sales’ Legendary Leonardo DiCaprio Profile01:10:03 The Real Housewives Ultimate Girls Trip: Roaring 20th
4. Henrik Ibsen was a Gaggy Queen with Soraya McDonald and Juan Ramírez
56:51||Season 1, Ep. 4This 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 III02:17 Critics Soraya McDonald and Juan Ramírez on Theater03:38 Award Seasons, Broadway Revivals, and Artistic Merits09:21 The Evolving Conversation Around Colorblind Casting14:49 Identity, Representation, and the Commercial Stage25:46 Stage-to-Screen Adaptations and Modern Audiences28:42 Artistic Risks, Budget Constraints, and Regional Ecosystems33:16 Classic Playwrights, Tennessee Williams, and Henrik Ibsen37:57 The Public Theater’s Romeo and Juliet as Border-Crossed Lovers44:48 Pink, Live Hosting and The Tony Awards 47:30 Jukebox Musicals, Missy Elliot, and Pop Music Icons49:40 Vocal Mastery, Carmen Hip-hopera, and Historic Opera53:41 Closing Reflections on Dream Revivals and Nightmare Revivals
3. Audie Cornish: Is It a Good Interview or a Good Edit?
01:11:18||Season 1, Ep. 3This week on Feedback, Ira sits down with journalist, Engagement Party co-host, and NPR icon Audie Cornish for a conversation about interviewing, internet culture, and what makes a great conversation actually work. Together, they unpack the ingredients of a successful culture podcast, the ever-changing social media landscape (from Reddit to Bluesky to Threads), the evolution of the Heated Rivalry fandom, and the ways reality TV has reshaped how we communicate. Plus, Audie shares why asking the right questions is an art in and of itself.00:00 Welcome to Feedback with Ira Madison III03:53 Audie Cornish on Interviewing and Meaningful Conversations08:12 What Makes a Great Culture Podcast?15:36 Navigating Reddit, Bluesky, Threads, and Today’s Internet21:08 Reality Television’s Influence on Modern Communication28:42 Online Identity and the Rise of “Main Character” Culture35:15 Journalism, Trust, and the Value of Thoughtful Reporting44:18 Reading Habits, Books, and Discovering New Writers50:27 Longform Writing, Attention Spans, and Media Consumption56:17 The Social Reckoning, Tech Culture, and Modern Storytelling01:02:45 Public Figures, Power, and Our Fascination with Tech Leaders01:08:30 Closing Reflections on Curiosity, Media, and Better Conversations