So True with Caleb Hearon

Episode: "Lilly Wachowski is Hosting Thanksgiving"

Date: November 27, 2025
Host: Caleb Hearon
Guest: Lilly Wachowski

Episode Overview

In this heartfelt and wide-ranging conversation, comedian Caleb Hearon welcomes filmmaker and writer Lilly Wachowski for a deeply personal, funny, and moving discussion just before Thanksgiving. The pair dive into their creative histories, the challenges of being queer artists, the ever-mutating meanings of art in a hostile world, and the importance of community—culminating in a love letter to chosen family, queer resilience, and bomb gravy recipes.

Key Discussion Points & Insights

1. Lilly’s Journey: Transition, Art, and Returning to Film (00:30–09:30)

• Finding Her Way Back: Lilly discusses her sabbatical from the film industry following her transition—feeling burnt out after working on "Cloud Atlas," "Jupiter Ascending," and "Sense8," and losing her artistic spark.
  • "I walked away because I felt like... there was a grind... my life was falling apart." — Lilly (03:51)
• Transition Through Grief & Art: During this period, she reconnected with her family, began painting with her mother, and gradually rekindled her creative passion.
  • "Painting... started sparking something for me as an artist again." — Lilly (06:54)
• ‘Work in Progress’ as Rebirth: Lilly became involved as executive producer on Abby McEnany’s “Work in Progress,” which brought her back to TV/film. She reflects on how working with a diverse and queer crew was nurturing and gave new purpose to her creative career.
  • "The crew looked like Chicago. It was…completely diverse... there's something that's left for me to do in this business." — Lilly (09:11)

2. The Challenges and Catharsis of Autobiographical Storytelling (12:16–20:49)

• Trash Mountain: Caleb shares their experience making the film “Trash Mountain”—for which Lilly was a champion and executive producer—about grief, family, and negotiating personal narrative in storytelling.
  • "It was so funny, so hilarious, but so true." — Lilly (12:16)
• Navigating Self vs. Character: Caleb discusses anxiety around being perceived as the character, and how shaping real experiences for film creates new kinds of vulnerability.
  • "I try not to create from that place ever...For the first time, I got real anxiety filming this movie..." — Caleb (14:43)
• Lilly on Catharsis in Writing: For Lilly, writing is an act of healing and self-service; storytelling becomes a space to process loss, especially after the death of her parents and through scenes in “Work in Progress.”
  • "I want my work to have a level of catharsis for myself." — Lilly (18:13)

3. The Evolution and Misappropriation of Art (21:10–26:49)

• Letting Go of Creative Control: The creators talk about audiences co-opting and misinterpreting their work, with "The Matrix" often cited by right-wing ideologues—a perennial frustration for Lilly.
  • "[Right wing] appropriates absolutely everything... This is what fascism does." — Lilly (25:08)
• Being Present in Creation: Lilly no longer focuses on pleasing everyone or achieving mass success, but instead on being present and finding beauty and community in the act of making art.
  • "I want to be present and relish every single day of the making that I have." — Lilly (22:36)

4. Queer Resilience, Joy, and the Purpose of Making Art (29:40–36:47)

• Queerness as Joy & Resistance: Lilly and Caleb discuss the power of queer community, finding “purchase in hostile environments,” and how making art is an active response to a world in crisis.
  • "Queerness, for me, is about joy. And so queer artists in their making... gives us signals to each other that we're not going anywhere." — Lilly (32:04)
• Message for Young Queer Creators: Lilly’s advice for emerging queer artists is to keep making art as a way to resist a culture of “unmaking.”
  • "We are in this period of unmaking. The only way to counteract that is to make... our joy... Those voids are nothing compared to what we bring to the table here." — Lilly (31:31)
• Transness Reflected in Storytelling: Coming out has given Lilly a higher vantage on her past work—seeing trans themes of liberation and love throughout her films ("Bound," "The Matrix"). Writing now is motivated by conscious healing and, lately, "trans rage."
  • "I see it because I'm like looking at it from this higher place... The cool thing about making art is that you can will things into being that you need to see in the world to help pull yourself along." — Lilly (36:47, 41:18)

5. The Midwest, Chosen Family, and Thanksgiving (45:46–57:20)

• Chicago Roots: Lilly explains her love of Chicago—the history, the anonymity, the catharsis of seasons, and distance from industry pressures of LA/NY.
  • "I could walk around in Chicago and be just another Chicagoan, anonymous." — Lilly (46:08)
• Holiday Traditions: Both reminisce about family-centric Thanksgivings, with Lilly lovingly planning an elaborate dinner—gravy praised as its own dish. Caleb describes their Kansas City gathering as a tapestry of friends and family, symbolizing chosen community and creative inspiration.
  • "This meal is... super important, and it takes days to prep... The gravy, Caleb, it's just knockout." — Lilly (54:39)
  • "It's the one holiday that my family has always... gotten together for." — Caleb (56:13)

6. Wisdom for Creators: Generosity in Writing and the “So True” Segment (57:21–62:24)

• On Scriptwriting: Lilly’s “so truism” is a pet peeve—disliking the placeholder "beat" in scripts, encouraging writers to be more generous and specific in their directions.
  • "‘Beat’… is lazy writing...I think it is a...ungenerous way for a writer to tell their story." — Lilly (59:39)
• On Collaboration: Both discuss the balance between detail and trust in scripts, avoiding over-direction that would stifle actors’ creativity.

Notable Quotes & Memorable Moments

• "I love you too." — Lilly to Caleb, opening (00:36)
• "Painting... started sparking something for me as an artist again." — Lilly (06:54)
• "The thing that was missing...was that I had satisfied a lot of stuff for myself as an artist. But getting to work on that show and hiring the people that we hired... there's something that's left for me to do in this business." — Lilly (09:11)
• "This movie is about the way that queerness springs up everywhere... even in the most hostile environments." — Lilly recalled by Caleb (29:40)
• "We are in this period of unmaking. The only way to counteract that is to make... our joy is going to... fill those voids." — Lilly (31:31)
• "Who will ever love this?" — Lilly on the internal fears of being trans (38:25)
• "Cooking, to me, is something that I've really used lately as, like, meditative practice." — Lilly (53:35)
• "It's the best... it's my organizer friends, my artist friends, my buddies from college and high school... one day a single year where you get to do that. It's pretty nice." — Caleb (56:43)

Important Timestamps

• Lilly’s creative hiatus, family & transition: 00:30–09:30
• Work in Progress, diverse crew, new purpose: 09:30–12:16
• On Trash Mountain, writing from truth: 12:16–18:13
• Handling being read into one’s art: 18:13–21:10
• Co-option/the Matrix: 21:31–26:49
• Queer resilience—finding joy, making art: 29:40–36:47
• Chicago & Midwest influence: 45:46–49:56
• Thanksgiving & chosen family: 52:27–57:20
• Lilly’s “so truism” about writing, collaboration: 57:21–62:24
• True or False Game (lighthearted close): 62:24–66:22
• Sign-off, words on mutual support: 66:44–67:07

Final Thoughts

This episode captures the warmth, humor, and honesty that define both Lilly Wachowski’s and Caleb Hearon’s creative worlds. It explores the deep interconnection between life and art, the joy and rage of queer existence, the power of community rituals, and the imperative to keep making art—no matter how hostile the wider world may feel. As they close, Lilly summarizes:

“I think just, like, hold each other up. That's all we got to do. That's how we get through this. Keep getting into community and grabbing hold of people and make sure they're staying on their feet.” — Lilly (66:51)

For listeners: Whether you’re a young queer artist, a film lover, or just prepping your gravy, this episode is a nourishing, affirming call to keep making things—and to find joy, connection, and healing in art.