Phoebe Robinson is here, and she has thoughts! She joins Ira for a conversation about pop culture, comedy, and saying exactly what you think. They get into Phoebe’s viral wig rants, the strange state of celebrity podcasts, and why she wants people to stop treating pop culture commentary like the news. They also discuss Phoebe's return to stand-up, and what it really means to be in your "Rich Auntie" era.

Buy tickets to Phoebe's Feral and Fired Up! Tour: https://www.phoeberobinson.com/

00:00 Ira Talks About Dolly Parton

02:48 Phoebe Robinson’s New Book, “Rich Auntie”

05:37 Friendship, Boundaries, and Getting Older

06:53 Writing Books and Finding Her Voice

13:27 The Evolution of Podcasting Since “2 Dope Queens”

18:01 Phoebe’s “Wig Rants” and Sharing Opinions Online

24:00 Why She Doesn’t Have an Opinion on Everything

28:06 Creating Her Own Opportunities

31:44 The Responsibility of Comedy

37:49 Creating Tiny Reparations Books

41:07 Advice for Becoming a Better Writer

46:36 Giving Artists More Time to Create

48:30 Pop Culture, “The Valley,” and What She’s Watching

52:26 Problematic Celebrity Crushes

54:00 The Worst Things She’s Spent Money On

55:45 Books, London, and Lady Gaga

57:28 Why Men Should Read More Fiction

01:01:13 Do People Actually Read the Books They Post Online?

01:04:14 Book Covers and “You Can’t Touch My Hair”

01:05:19 Phoebe’s Dream Podcast Guest

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This week, Ira is joined by bestselling author Angela Flournoy for a conversation about writing, reading, and trusting your audience. Together, they discuss Angela’s writing group back in LA, the joy (and frustration) of Goodreads, why some books teach you how to read them, and the delicate balance between guiding readers and letting them figure things out for themselves. Plus, Angela explains why she's actually pro-feedback — and why every writer should resist the urge to Google themselves.

00:00 Intro: Ira’s Reading Habits and Tips from Well-Read New Yorkers

02:35 Angela Flournoy and The Wilderness

08:15 Writing a Novel Over Ten Years

10:57 Life as a Writer

18:16 Writing for the Page, Not the Screen

23:27 Toni Morrison and Teaching Readers How to Read

31:02 Writing Routines and the Pomodoro Method

37:50 Books, Prizes, and the Writing Life

43:52 Knowing When It's Time for a New Book

49:13 The Novel, Short Stories, and The Wilderness

52:59 Ghosts, Grief, and Loss

54:40 Friendship and Making New Friends

59:42 What Fiction Reveals About the Writer

1:02:15 Classic Books and Reading in 2026

1:05:55 Teaching Writing and MFA Programs

1:10:00 Goodreads, Reviews, and Feedback

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This 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 Episode

04:21 Josh Lora Joins Ira: Christopher Nolan & The Odyssey

07:40 The Odyssey, Identity & Representation

12:05 Christopher Nolan’s Fascination With Masculinity

20:45 Masculinity, Guilt & the “Great Man”

24:29 Interstellar, Spider-Man & Male Loneliness

32:29 TikTok, Beauty Standards & Online Culture

41:09 Daria, Punk & the Death of Counterculture

46:55 Celebrity Fandom & the Rise of Stan Culture

52:58 BookTok, Reading Culture & DNFing Books

56:06 Why Internet Culture Is Getting Darker

01:06:41 Reality TV, Netflix & the Death of the Reality Star

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This 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 Review

8:50 Gibson Johns Joins the Show

10:45 How Gibson Went From Bravo fan to Bravo Journalist

15:29 Critic or Interviewer? Where Gibson Fits In

21:50 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 Discourse

38:50 Franchise Identity & When a Show Becomes "About the Show"

44:41 Hulu's New Reality Shows

47:53 Threads Discourse Has Gone Feral

50:12 Ira's Apartment Fire Cameo on RHONY: In the City

52:27 Gibson's Coverage of the Osefo Drama

55:43 Caller: Kelly Bensimon & the Carl Radke Question

59:47 Ex-Housewives Spinoffs & Social Capital

1:04:39 The Men of Southern Charm

1:08:34 Caller: Who Is Rhode Island's Villain?

1:12:05 Rapid Fire: Bravo Superlatives

1:14:35 Lindsay Hubbard on Threads, Jules & Closing Bits

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New 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 – Intro

6:04 – Madonna's Club Confessions NYC

10:05 – Connie Fleming: Working NYC's Legendary Club Doors

14:21 – The Art of Curating the Perfect Nightlife Crowd

17:32 – Drug Culture in the Clubs

21:05 – Boy Bar, Drag, Fashion & NYC Performance Art

26:13 – Before TikTok: The Lost History of Club Documentarians

29:20 – Fighting for LGBTQ Rights Then—and Now

32:21 – When Queer Life Moved From the Dark to the Light

39:46 – Fire Island, Inclusion & Finding Community

47:42 – Listener Call: Biggest Misconceptions about Connie and Lina

53:52 – The Music That Still Moves Them

58:11 – Connie's First Night at Basement

1:00:54 – Are Phones Ruining the Club?

1:04:20 – Connie and Lina's Friendship Story

1:06:32 – Social Anxiety & Club Etiquette

1:10:13 – Listener Call: When Should You Leave the Afters?

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As 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 III

01:02 Becoming Marlena Evans and 50 Years on Days of Our Lives

05:17 Life as a Soap Actor

06:36 Working with Writers and Creating Iconic Storylines

09:11 Her Twin Sister's Unexpected Soap Opera Career

12:04 Soap Deaths, Fan Outrage and Bringing Characters Back

15:16 Favorite Storylines: Possession and The Salem Stalker

25:13 How Budget Cuts Changed Days of Our Lives

27:39 Celebrity Fans and Connecting with Viewers

31:18 Daytime TV's Legacy

34:16 Ensemble Storytelling, Favorite Castmates, and John and Marlena

40:12 Rivalries, Friendships, and Playing Marlena Today

43:09 Acting Advice and Guest Starring on Hacks

45:45 Future Crossovers, Dream Roles, and What's Next

47:11 Why Marlena Will Always Be "Doc"

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This 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 Hits

04:47 Summer Time Do's and Don'ts with Chrissy and John

10:07 Shein, 7 Jeans, and Every Brand in Between

16:57 Magazines vs. Influencers

22:25 Magazine Editors & Iconic Covers

31:44 Queer Fashion & Heated Rivalry

37:01 Press Tours, Timothée Chalamet & Celebrity Fashion

47:01 The Reality of Celebrity Styling

50:15 Influencer Culture vs. The Fashion Industry

59:04 FWD JOY, Newsletters & Building a Brand

01:02:46 Knicks Jerseys... It's Still That Deep

01:06:48 Carrie Bradshaw & Knowing Your References

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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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