Long Winded with Gabby Windey

Episode Title: Jinkx Monsoon
Date: March 12, 2026
Guest: Jinkx Monsoon – two-time RuPaul’s Drag Race winner, Broadway star, actor, musician, comedian, pop culture icon

Episode Overview

In this energetic, candid, and deeply insightful episode, Gabby Windey welcomes Jinkx Monsoon for an intimate and wide-ranging conversation. They plunge straight past standard celebrity fare and dive into the personal: queerness, gender identity, addiction, chosen family, mental health, intergenerational change, and pop culture—from drag to Broadway and beyond. The episode’s tone is marked by playful irreverence, vulnerability, belly-laughs, and real-deal wisdom.

Key Discussion Points and Insights

1. The Power of Chosen Family and Staying Grounded

[01:31–06:25]

• Close Bonds with Fellow Drag Queens: Jinkx discusses the chemistry and working relationship with Monet X Change and Bob the Drag Queen. Gabby notes the “special kind of chemistry” they exude.
• Grounding in Old Friendships: Jinkx emphasizes the value of surrounding herself with friends who knew her before fame.
  • “A lot of the people that I work with are just the same people who have been there from before any kind of success… They're the people who I trust the most because I trusted them before I was anything.” (Jinkx, [04:05])
• Not Getting Lost in Self-Regard: Jinkx thoughtfully sidesteps Gabby’s “you’re so inspiring” praise, redirecting to the idea of “paying it forward” and the importance of community celebration.
  • “If I start getting lost in the thoughts of like it being about me, then I feel like that's when I've kind of gone down my more selfish routes...” (Jinkx, [02:20])

2. Drag Origins, Family Support, and Creating Persona

[09:06–14:56]

• Discovering Drag at 15:
  • “Yeah. In Portland, Oregon.” (Jinkx, [09:07])
  • Early drag costuming was sourced from thrift shops (Buffalo Exchange, Red Light) and even her grandma’s friends.
• Grandma’s Influence: Jinkx’s grandma not only helped with early costumes but inspired the “old lady” drag persona.
• Building a Stage Persona:
  • “When I've taught drag workshops, I always say start with doing an impression of your mother...” (Jinkx, [10:25])
  • Jinkx initially incorporated personal struggles—growing up with an alcoholic parent—into her character, turning pain into comedic performance and self-rewriting.
• Sobriety and Evolution:
  • “I haven't drank for six years now. Six plus years. Thank you. Really good decision for me.” (Jinkx, [11:20])
  • Transitioned Jinkx from an “alcoholic” persona to a “stoner,” reflecting her real-life shift to being California sober.
  • “I just kind of phased it out. Now she's a stoner like me, you know?” (Jinkx, [12:12])

3. Addiction, Mental Health & Medication

[14:38–19:11]

• Addiction Stories and Perspective:
  • Jinkx shares about moving from straight-edge to struggling with alcohol, then quitting to preserve positive relationships.
  • “I had drag in my life without alcohol, and I had these friends in my life without alcohol. And I had to tell myself I had positive feelings towards these things before alcohol was in my life.” (Jinkx, [14:56])
• Medication Stigma and Self-Awareness:
  • Open discussion about antidepressants and mood stabilizers:
    • “What if I can find a medication that's better... It made me manic for a little bit.” (Gabby, [15:04])
    • “You know, why question what's working?” (Jinkx quoting her psychiatrist, [15:49])
  • Wellbutrin “nullifies the effects of weed,” which Jinkx finds makes her a “high functioning stoner.” (Jinkx, [18:05])

4. Intergenerational Trauma, Change, and Acceptance

[19:53–25:33]

• The Impact of Societal Change:
  • They reflect on trauma endured by anyone alive in the past twenty years (“...we've been through some fucking shit.” – Jinkx, [19:53]).
• Navigating Generational Gaps on Gender and Sexuality:
  • Jinkx calls out older generations’ discomfort with topics like being trans, using a pointed analogy: “You're asking someone to live their life uncomfortably so that you can be a little more comfortable.” (Jinkx, [22:36])
  • Gabby shares coming out as a lesbian and family reactions: “I don't expect you to totally... understand, like my experience...but at least, like, you know, just. Yeah. Still treat me like a normal relationship.” (Gabby, [24:13])
• Family Lessons:
  • Jinkx’s grandfather’s reaction: acceptance without full understanding, focusing on loving his grandchild regardless ([24:42]).

5. Untangling Gender, Intersex Awareness, and Societal Constructs

[27:01–42:13]

• Jinkx’s Mother’s Intersex Story:
  • Her mother discovered she was intersex in her 60s after a medical investigation led to the finding of an underdeveloped testicle ([27:43–28:07]).
  • This revelation transformed her acceptance of Jinkx’s trans identity: “No problems with My pronouns, no problems with my chosen name...the script was flipped for her.” (Jinkx, [29:10])
• Reflections on Gender as a Spectrum:
  • “If there is a natural way to things, the natural way to things is that we lie somewhere on a spectrum.” (Jinkx, [30:03])
• Visibility & Suppression of Intersex Realities:
  • “There are already intersex people in the public eye who are trying to suppress this stuff...if we start pulling that thread, this whole fucking thing falls down.” (Jinkx, [31:30])
• The Dangers of Binary Thinking:
  • Jinkx and Gabby connect the medicalization of “fixing” intersex children to current anti-trans sentiment: “The boogeyman surgery that they used to villainize us is actually being performed in straight communities without autonomy.” (Jinkx, [38:26])
• The Biological Irony:
  • “You want to quote Biology...Are ignoring the answer that's already in front of you.” (Jinkx, [41:52])
  • “If you want to quote the Bible and say God doesn't make mistakes… then intersex people… you’re the one trying to undo God’s work.” (Jinkx, [41:54])

6. Pop Culture, Judy Garland & Queer Legacy

[43:04–51:25]

• Portraying Judy Garland in ‘End of the Rainbow’:
  • “I am so excited to play Judy Garland.” (Jinkx, [43:11])
  • Judy’s struggles are comparable to Britney Spears', with young female stars repeatedly exploited, manipulated, and denied ownership of their work ([44:11–46:02]).
  • They reflect on cycles of villainizing powerful women: “A woman shows one, like, blip of frustration or anger or something, and now she’s a (bitch) for life.” (Jinkx, [47:17])
• Women Being Taught to Stay Quiet:
  • “You told me to be good. You told me to be quiet, and you’re wrong. It got me nowhere.” (Gabby referencing Florence + The Machine, [49:20])
• Success, Authenticity, and Breaking Barriers:
  • “I just know I don’t care so much about the success. I really just want to like the work that I’m doing.” (Jinkx, [49:44])
  • “People tried to convince me I wouldn’t get to do both in life [drag and theater]...and then it turns out that was another Lie.” (Jinkx, [50:49])

7. Community, Jealousy, and Inter-Generational Queer Dynamics

[51:25–54:03]

• Envy Among Marginalized Groups:
  • “So the people who get angry at you for being who you are... it's because you wish you were me.” (Jinkx, [52:40])
• Older Queer Resentment:
  • “Older queer people are angry the younger queer people get to be as queer as they are...you should be proud that in your way, somehow you proud. You are part of why these younger, like, yeah, Drag race season five, 15 years ago is part of why there's a drag race season 18.” (Jinkx, [53:15])

8. Societal Cycles, Progress & Hope

[54:03–56:48]

• Pendulum of Progress:
  • Gabby and Jinkx discuss the cyclical backlash to progressive gains:
    • “Whenever the pendulum swings one way...the reason why the pendulum is so far in the conservative side is because too many people were made uncomfortable...and we're too convinced that the discomfort was our fault.” (Jinkx, [54:26])
  • Frustration at having to “fight about the same thing over and over and over again.” (Jinkx, [55:00])
  • “It feels so late. It's not sustainable where it's at. So, yeah, it's frustrating. And also, every time you watch someone wake up, that's another person who has now come to this side, you know?” (Jinkx, [55:48])

9. Astrology, Superstitions & Witchy Wisdom

[66:09–79:59]

• Astrology as Relationship Map:
  • They compare signs, reflect on how parents and friends’ signs influence them.
  • “Virgo and Scorpio really are good friends, but they also...if they can be honest with you, they'll be one of the best friends you'll ever have.” (Jinkx, [79:02])
• Superstitions and Ritual:
  • Knocking on wood before shows, carrying a stick “for luck,” and exploring whether these are magical beliefs, OCD, or ADHD.
• Precognition & Family Witchiness:
  • “All the women in my family...could always predict things and...had premonitions and prophetic dreams.” (Jinkx, [67:51])

10. Sex, Singing, and Unfiltered Humor

[59:04–61:38]

• Sexual Brags (with Jinkx’s Signature Wit):
  • “Statistically speaking, I am vetted. I give good head from so many different people. We see what you’re working with around the world.” (Jinkx, [61:29])
• Singing and Oral Technique:
  • “Because I'm a singer, I know how to open my throat... And circular breathing... I oftentimes feel also that I sing better after giving head.” (Jinkx, [65:08])
• Global Encounters:
  • Cheeky recounting of sexual escapades on tour (“What I'm trying to say is, around the world, I'm known for being a. And I.” (Jinkx, [63:49]))

Notable Quotes & Memorable Moments

• “If I start getting lost in the thoughts of like it being about me, then I feel like that's when I've kind of gone down my more selfish routes…these days I do something and then I hear from the community like this meant Something to me because. And I'm like, oh, it's not just me. It's everything happening right now.”
  – Jinkx Monsoon ([02:20])
• “You can't just lose part of the ecosystem and expect everything to go on. It's like. It's why we're scared of losing the honeybees.”
  – Jinkx Monsoon ([34:23])
• “If you want to quote the Bible and say God doesn’t make mistakes… then intersex people… you’re the one trying to undo God’s work.”
  – Jinkx Monsoon ([41:54])
• “[Judy Garland’s] is one of the earliest examples of conversations we've been having more recently about the double standards for women in entertainment. …if you know Judy Garland's story and, you know, Britney Spears story, you're like, how did this happen again?”
  – Jinkx Monsoon ([44:02])
• “I just know I don't care so much about the success. I really just want to like the work that I'm doing.”
  – Jinkx Monsoon ([49:44])
• “Older queer people are angry the younger queer people get to be as queer as they are. ... You shouldn't be angry. You should be—well, you should be happy that they don't [have to hide].”
  – Jinkx Monsoon ([53:15])
• “I oftentimes feel also that I sing better after giving head. ... The vocal cords are a muscle like anything else. So you work all that muscle, you're gonna have more stamina.”
  – Jinkx Monsoon ([65:16])

Important Segment Timestamps

• 00:00–01:00 – Ads and Gabby introduces Jinkx Monsoon
• 01:31–06:25 – Importance of long-term friendships leading to true self
• 09:06–14:56 – Drag origins, relationship with grandmother, and personal identity
• 14:38–19:11 – Addiction, sobriety, mental health, medication
• 19:53–25:33 – Trauma, generational differences, acceptance, and family
• 27:01–42:13 – Intersex experiences, gender as spectrum, science & faith, societal implications
• 43:11–51:25 – Judy Garland, women in showbiz, cycles of exploitation
• 51:25–54:03 – Jealousy and community in queer worlds
• 54:03–56:48 – Social progress, pendulum swings, exasperation and hope
• 66:09–79:59 – Astrology, witchy practices, superstitions, family dynamics
• 59:04–65:34 – Unfiltered stories of sex and singing prowess

Final Reflections & Episode Tone

Gabby and Jinkx’s rapport is giddy, irreverent, warm, and nourishing. They bring taboo topics into the open, make the personal political, and flip cliches with wit and honesty. There’s deep appreciation for queer lineage, honesty about healing and self-discovery, and a welcome embrace of difference—peppered with wry, raunchy comedic timing. The episode closes with a celebration of being unapologetically yourself: “We could talk about cereal for hours. We just have big opinions on things. That's why we became drag queens in the first place.” (Jinkx, [85:59])

See Also

• Jinkx Monsoon: starring in End of the Rainbow (May–June, Soho Theatre, UK)
• Keep up with Gabby Windey on future episodes of Long Winded

Summary by Podcast Summarizer AI