Lilly Wachowski is Hosting Thanksgiving

So True with Caleb Hearon

Headgum

Society & Culture, Comedy Interviews, Comedy

4.9 • 975 Ratings

🗓️ 27 November 2025

⏱️ 67 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Welcome! This week’s guest is the legendary Lilly Wachowski! Lilly and Caleb talk making a movie together, living in Chicago, the lasting legacy of The Matrix films, the importance of queer art in this day and age, stew, and so much more!

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Lilly has no social media! Happy Thanksgiving!

Follow the show! @sooootruepod

Follow Caleb! @calebsaysthings

Produced by Chance Nichols @chanceisloud

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About Headgum:

Headgum is an LA & NY-based podcast network creating premium podcasts with the funniest, most engaging voices in comedy to achieve one goal: Making our audience and ourselves laugh. Listen to our shows at https://www.headgum.com.

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So True is a Headgum podcast, created and hosted by Caleb Hearon. The show is produced by Chance Nichols with Associate Producer Allie Kahan. So True is engineered and edited by Nicole Lyons. Kaiti Moos is our VP of Content at Headgum. Thanks to Luke Rogers for our show art and Virginia Muller our social media manager.

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Transcript

Click on a timestamp to play from that location

0:00.0	This is a headgum podcast.
0:04.7	That script was a perfect example of the types of films and television that I'm trying to get made.
0:11.8	It was so funny, so hilarious, but so true.
0:19.4	Nice.
0:20.5	Nice. Sweet. We'll be clipping that. Lily. Hi. Hi, Caleb. I'm so glad that we're here.
0:33.9	Yay, me too. I just love you. I love you too. I'm so excited to have you here. We have been friends for a while now. Yes. Back in work in progress days. Back in work in progress. How did you get involved in work in progress? I actually don't know if I know that. This is the Showtime show with Abby McInney. Yes. Yeah. Well, Abby lives seven minutes from my house.
0:57.0	Yeah.
0:57.5	And we're old friends.
1:02.5	After I transitioned, I went through this searching phase where I was not sure I wanted to be in the movie business anymore.
1:14.3	And I started, I struck on this idea to do stand-up comedy.
1:25.7	I didn't know this, but I'm loving it.
1:28.5	And I took comedy classes when I was in college, and I liked it.
1:33.5	And it was, I thought it was like, I think it was like part and parcel of like the trans experience where you have to, you know, build up that callous of being out in the public and so um i started doing
1:47.1	this and um because abby worked in um uh second city and i oh theater here um i went and had coffee
1:58.3	with her because she was um with my partner, Mickey.
2:02.1	Yeah, who you know.
2:03.1	And we went and had coffee, and, you know, I started asking her about doing stand-up and stuff.
2:10.1	And she didn't know who I was.
2:15.3	And then we, you know, we started hanging out and we became super fast friends
2:22.1	and you know some years after that like a couple years she started working on this show
2:28.8	with her friend uh the co-creator tim and um they cooked up the basically the open of the show where the therapist dies.
2:40.4	Yeah.
	...

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