Long Winded with Gabby Windey

Episode: VMAs and Tr*mps Cankles

Host: Gabby Windey
Date: September 11, 2025

Overview

In this wide-ranging, irreverent solo episode, Gabby Windey dives into the chaos and emotional legacy of September 11, wrestles with pop culture’s evolution via her recent VMAs red carpet experience, and dissects (with her signature bluntness and medical savvy) the health of former president Donald Trump. With unexpected segues, candid anecdotes, and plenty of dark humor, Gabby dishes both high and low on contemporary American culture, celebrity, and politics.

Main Themes and Structure

• The haunting legacy of 9/11—personal, absurd, and conspiratorial takes
• A satirical deep dive into Trump’s health (and what it says about America)
• Reflections from Gabby hosting the VMAs red carpet: industry thoughts, pop culture critique, and fun celebrity encounters

Key Discussion Points and Notable Moments

1. “Haunted” by 9/11

[00:45–13:01]

• Gabby opens the episode reflecting (with characteristic dark humor) on sharing any milestone with 9/11:

  • “It’s haunted today. Today’s your birthday. You’re doomed.” [00:52]
  • Turns relationship milestones on 9/11 into dark jokes: “We fell in love on September 11th… your relationship is set to for sure implode from the inside out. It will explode. It’ll light up in flames just like the Twin Towers did from the inside out.” [01:20]

• Conspiratorial humor: Gabby riffs on how childhood exposure to 9/11 news shaped anxieties, throws in a 9/11 conspiracy theory (“there was a bomb planted and it didn’t actually crash from a high speed airplane”), and jokes about teachers being perverts and how history teachers “just carry on the legacy” of problematic founders. [01:36–02:42]

• Flying anxiety on 9/11:

  • Mocks people traveling on 9/11: “Why would you do that to yourself? Oh, you have to get back for work? Take a sick day.” [02:03]
  • Xanax jokes: “Xanax is good for the nerves, but it’s not good for bureaucracy… You won’t be able to see clearly.” [03:53]

• Air Traffic Control & Safety Critique:

  • Points out America’s lagging technology for air traffic safety; advises listeners to stay away from tall buildings even on September 12th and 13th. [05:15]

• Critique of lost fail-safes (phones on planes):

  • Reminisces about emotional 9/11 voicemails and the ability to say goodbye because “we had phones on the planes.”
  • Laments removal of phones from airplanes: “No, we’re not worried. We’re just going to take away all the phones, so if there’s ever an emergency, you won’t be able to call home.” [08:16]
  • Critiques unreliable Wi-Fi claiming, “There’s no vibes, period. There’s nothing,” mocking airline Wi-Fi and technology gaps. [10:15]

2. Medical Satire: “Tr*mp’s Cankles”

[13:45–27:22]

• Gabby moves to a lighter, still scathing, segment:

  • Introduces Trump's “cankles” as “a representation of the state of our country by way of his ankles, or lack thereof.”
  • Blends medical expertise and biting satire:
    • “He needs 40 mgs of Lasix stat... and you have to give him the urinal because his old ass isn’t getting up frequently to pee.” [14:04]
    • Diagnosis play-by-play: fluid retention, potential need for dialysis, peripheral vascular disease, and how “all of the oxygenated blood is sitting around his ankles. That’s where all the decision making is in regards to our country.” [14:49]

• Policy and Care Satire:

  • Points out the gendered inequity in maternity leave:
    • “If this was a man and he tore from his saggy scrotum to his asshole while giving birth... I guarantee you we would have a longer maternity leave.” [15:29]

• Bipartisan shade:

  • “This is not a partisan issue. It’s very bipartisan. I was open and concerned about Biden’s sundowners. Poor Jill, hopefully she has Haldol on hand after 5pm when the sun sets.” [16:35]

• Stroke/pedophile joke string:

  • “He’s got to be on a blood thinner... being a pedophile has to increase your risk of stroke. Those disgusting, depraved, banal... thoughts must build plaque in your veins.” [18:14]

• Drag/bread jokes:

  • Extended riff on Trump’s health and his MAGA hat:
    • “This cream is called Monistat. You and I use it for our pussy. He uses it for his flaky scalp because the moisture is sitting there... The yeast has evolved into sourdough.” [20:33]
    • “He is a queen. He is really the president of camp... He would definitely, he would get the pork chop. He’d be out first [on Drag Race].” [21:25]

3. Gabby’s Experience Hosting the VMAs

[27:22–end]

• Behind the Scenes:

  • Gabby explains her role hosting the MTV VMAs red carpet.

    • “As you guys may or may not have seen, I hosted the red carpet for the VMAs... It was fine. I don’t want to have to fangirl. I want my fangirling to be really natural. But... I found it to be a little forced, which is a characteristic of a great journalist.” [27:22]

  • On being the interviewer, not the interviewee:

    • “I want to be the one being interviewed... Who’s going to ask me a question?” [28:13]

• Red Carpet Team Shoutouts:

  • Big praise for her styling and glam team, and for producer Cheryl (bonding over “cult ran coffee shop” in Colorado). [29:18]

• Reflections on VMAs Then vs. Now:

  • Nostalgic for Britney Spears’ iconic moments:
    • “But it is kind of sad... She was terrified of that snake, but she had to do it and she did it like a professional.”
    • Dissects risks in pop history—conservatorships and tigers—“We’re lucky she’s alive.” [31:27]

• Pop Fame Work Ethic:

  • Laments the insatiable demand:
    • “You cannot stop. It’s a hit of a drug. Fame. It really gets you.” [33:25]
  • Observes Lady Gaga’s hectic routine: speech, tears, concert—all in one night.

• Desire for Public Beef:

  • “I do think we should bring back public beefs. Why am I walking on eggshells? I do have some shit to say.” [30:15]
  • Dissects Mariah Carey/Ariana Grande dynamic and Courtney Love’s Taylor Swift criticism:
    • “Let’s just see a little drama, like when Courtney Love tweeted that Taylor Swift wasn’t a real artist...” [36:43]

4. Candid Celebrity Interactions & Observations

[44:00–47:45]

• Interview Highlights:

  • Ashley Simpson: Warm, friendly, happy to return to VMAs after a 17-year hiatus.
    • “She really embraced me like she knew me. She was so warm.” [48:26]
  • Britney Snow: Induces “gay panic” in Gabby, praised for positive lesbian representation.
  • Sierra: Friendly but business-focused—“She talked at me... she needs to get her spiel out.” [49:20]
  • FKA Twigs: Quiet, ethereal; wore “fecal matter” designer, which Gabby mishears: “She had this really sweet angel voice that I could not hear... I asked her to repeat it.” [49:47]
  • Youngblood: Charismatic, brings “rock star” energy back to pop; Gabby muses on masculinity and emo aesthetics. [41:32]
  • Doja Cat: Down for a viral red carpet bit—eating lipstick.
  • Tate McRae: Praised for her flexibility and contemporary dance; Gabby laughs about obsessively asking artists if they can do the splits.
  • Cat’s Eye: Sweet, full of earnest energy; Gabby refuses to judge their outfits: “They’re all drop dead. They’re the most beautiful, most talented people, literally by competition proven.” [47:15]

• Gripes and Industry Snark:

  • Points out the performative nature of drag queen alliances for mainstream female pop stars.
  • Wonders aloud why no lesbians are hired as “props” for mainstream music careers: “As a lesbian, how come nobody likes to surround themselves with lesbians for fun and for success? I would like to be used as such, but no one seems interested.” [38:15]

Notable Quotes

• On 9/11 and flying anxiety:
  • “If you’re flying today, why would you do that to yourself?... A glass of wine isn’t going to cut this one. You’re going to need a Xanax.” [02:03]
• On Trump as a patient:
  • “He needs 40mgs of Lasix stat... give him the urinal because his old ass isn’t getting up frequently to pee.” [14:04]
• On VMAs/media industry:
  • “I want to be the one being interviewed... Who’s going to ask me a question? I have some shit to say.” [28:13]
• On the endlessness of pop stardom:
  • “You just cannot stop. It’s insatiable. It’s a hit of a drug. Fame. It really gets you.” [33:25]
• On public beefs and authenticity:
  • “Let’s just see a little drama, like when Courtney Love tweeted that Taylor Swift wasn’t a real artist...” [36:43]
• On celebrity diversity representation:
  • “I would like to be used as such, but no one seems interested. Diversity, hello. Equal opportunity, hello.” [38:15]

Time-stamped Segment Breakdown

• [00:45–13:01] 9/11: Dark reflections, conspiracy, anxiety, airline/tech gripes
• [13:45–27:22] Trump and presidential health: Medical roast, bipartisan shade
• [27:22–44:00] VMAs recap: glam squads, anecdotes, pop work ethic, drama in the music industry
• [44:00–47:45] Red carpet celebrity encounters, pop culture analysis, diversity gripes

Closing Remarks

Through characteristic wit, snark, and the lens of a health professional-turned-pop-culture-podcaster, Gabby Windey offers both levity and real talk. Whether poking fun at presidents’ health, longing for the days of public diva feuds, or longing for deeper representation in mainstream pop, Gabby’s “Long Winded” lives up to its name—in the most entertaining way.