In 2016, as Hamilton was entering the cultural zeitgeist, Gillian Pensavalle began The Hamilcast: A Hamilton Podcast. She interviewed the show's creators, cast members from around the world (including original cast members Renée Elise Goldsberry and Leslie Odom, Jr.), and theatre people about their love for Lin-Manual Miranda's creation. Every episode deep dived diving into the minutia of the hit musical. Now, after 10 years and 500 episodes, The Hamilcast is coming to an end.

Playbill chatted with Pensavalle to discuss why she took her shot at making this podcast, details from Hamilton that most hardcore fans miss, and a memorable text message from Miranda himself.

When was the moment that you realized that a Hamilton-focused podcast was something that you had to create?
Gillian Pensavalle: I was talking to my best friend, Ashley, who has been on the Hamilcast many times. We've known each other since we were 13 years old. She played me the cast recording because it had just come out on NPR in October of 2015. Ashley has never steered me wrong when recommending any movie, any band, or any album. We were listening to it, and I immediately fell in love. At this time, I had not seen the show yet, but I was eventually talking about Hamilton so much that I started to see people getting really bored. They were like, “here she goes again.” I just remember sitting in my apartment thinking, "I think this is a podcast," which is another weird thing, because I had not listened to podcasts. I have ADHD, so if it's a visual medium, it's hard for me to follow it, and I didn't have any equipment for podcasting. I knew nothing. I had no idea how I was going to do this, but I was determined because I knew that there were people that wanted to talk about it. I wanted to do it with Ashley, but she just didn’t have the bandwidth for it.

I asked a friend of mine at the time if she wanted to be a part of it with me and said, “just come over and talk about your favorite thing, and I'll do the rest.” So, we started recording. I barely edited that first episode, and it was released in January of 2016 on a Saturday. I recorded it on a camcorder, because my husband, Mike, and I had made two seasons of a web series, so that was the only equipment I had. I wasn't even thinking. I just sort of jumped in and just did it. 

I just wanted to talk about Hamilton and find other people who wanted to talk about it. Almost instantly, I was getting emails from South Africa, and all over the world, because everyone was excited to engage in the conversation. 

Prior to the Hamilcast, you were not a podcaster. Was there a moment where you said to yourself, is this becoming my career?
It's funny because I’m one of those people with a communications degree. I wanted to be like a VJ, when that was a thing. I wanted to simply be myself. I wanted to speak to people about things that they love: music, pop culture, etc. I worked in radio for a long time and I worked at 92.3 K-Rock here in New York City; I just liked having conversations with people about their passion for music and culture. I didn't have a degree in anything else, and I didn't know what else to do. I was bartending and doing all these freelance gigs. And then I fell into podcasting with the Hamilcast, which was a total passion project. The Hamilcast led me to Patrick Hinds, who was doing the Theater People podcast at the time. Patrick reached out on Twitter and said, “Welcome to the theatre podcasting world. Let me know if you ever need anything or want to be friends.” That meant so much to me because no one else did that. I was seen as this outsider, or this idiot fan girl, so his offer meant a lot. We would meet for happy hour, and conversations eventually turned into talking about the latest documentary we were watching. This all led to True Crime Obsessed, where we recap true crime documentaries, and now that has become a thriving business. 

To quote Hamilton, it was like fanning this spark into a flame. It was something that I felt that I wanted to do, and it led me to my career as a podcaster. When I say that Hamilcast has changed my life, I'm not being hyperbolic. It has changed my life in ways that I never could have imagined.

How has your relationship with the musical changed or evolved since you began Hamilcast?
From the beginning, Hamilton and Lin loved the podcast and encouraged what I was doing. Hamilton said yes to us using their logo and music. We exist in tandem, yet also separate. I wanted guests to feel open and honest and share their experience with the show. Guests could essentially let their hair down and really be their authentic selves. Podcasting is all video now—except for the last few recordings with the cabinet and with Leslie Odom Jr, I never cared about video recording, because it sort of makes people feel like they're on. When recording the Hamilcast, we're just having a conversation, and it goes wherever you want it to go. I always say to the guest, this is your show and I’m following your lead. Sometimes we talk about Hamilton for 10 minutes and then other topics for three hours.

When did you finally get to see the Broadway production?
I started the podcast at the end of January of 2016, and I was very good at losing the ticket lottery. It's funny because I was going back through my emails, and I almost succumbed to Craigslist, because I was just desperate for tickets. But there was a phenomenally generous benefactor who reached out and said that they wanted to gift me tickets to the show. I finally saw the show in April of 2016. I will never forget the feeling of the ticket being scanned and getting to experience it live for the first time.

In your interviews with the Cabinet—Lin-Manuel Miranda, Andy Blankenbuehler, Thomas Kail, and Alex Lacamoire—what are some of your favorite takeaways from those episodes?
The general theme is collaboration and how they work together. Everyone's very fascinated by that. All the Patreon Peeps are always asking, “How can I do that in my life?” People want to collaborate the way they do. Listeners enjoyed discovering that Lin learned stuff about the choreography in his own show from the Andy Blankenbuehler episodes. After Andy’s episode, Lin texted me and said, “I didn't know there was book choreography in ‘Aaron Burr, Sir.’ I had no idea.” It’s so wild. They just let everyone create and do the best job they need to do. The Alex Lacamoire episodes are always legendary because he comes with a keyboard. He never comes to a recording empty-handed. He will break down little moments. The first time he came on, we did a whole breakdown of “The Schuyler Sisters” and talked about moments that came out of all the demos. Andy has many references when he's teaching the choreography that performers won’t know. He'll be like, “Oh, that's the Bruno Mars moment.” And I'm like, “Why is it Bruno Mars”? And he said, “I don't know. It just makes me feel like Bruno Mars. I can't tell people it's the Bruno Mars moment. Because that moment only makes sense to me."

What is a Hamilton moment, lyric, or piece of trivia that you think even the most hardcore fans sometimes miss?
People can watch Hamilton all the time now on Disney+ in addition to seeing the production on Broadway or on tour. My suggestion when watching more than once is to keep your eye on the surroundings. Who's watching what? Who's looking down? There are moments where you realize, "Oh, Eliza has been watching this entire thing from the surrounding."Or, realizing that Aaron Burr is not singing in “My Shot”—Aaron Burr is on the stairs and he's doing the choreography, but he doesn't look thrilled, and he's not singing because he can't bring himself to be a part of it in that moment. I think that's brilliant. Another fun thing you can do is to choose one character and follow their journey throughout the show: It could be Man #4, or Woman #2, or it could be Angelica, or anyone, and follow them. Someone else to watch is Maria Reynolds. She is the person who hands him the quill to write the Reynolds pamphlet, and she is in the background dressed in the red. There is another funny moment too, and you would never know if you weren’t speaking to people involved in the show, and it happens very early on. In “Aaron Burr, Sir” and in “My Shot,” where they are at the tavern, the books that they're reading are true 1700s erotica. They are reacting and they're pointing to real erotica from the time.

Which song or character resonated with you the most?
From the beginning, “Yorktown” has always been my favorite. “Satisfied” is a very close second. When Hamilton came into my life, I felt sort of lost. I didn’t know what I was looking for. So, Hercules Mulligan's line, “when you knock me down, I get the fuck back up again” really resonates with me. It has helped me say to myself “I can get through this,” and I've taken that with me ever since. As I reflect over these 10 years and 500 episodes, I'm also feeling such a strong connection to the lyric, "What are the odds the gods would put us all in one spot?" That one hits me really hard these days. We're living in a time where we are having these conversations about Hamilton and life in general. I'm a big believer in the universe and the stars aligning, and we managed to do that.

Can you tell our readers a little bit about the Hamiltome?
So, the Hamiltome is a book that I had nothing to do with at all. Hamilton: The Revolution is its official title. It is a deep dive behind-the-scenes book about how the show came together. It's beautiful. It is stunning. The art is unbelievable. Everyone has their own little section, all the actors and it also has all the lyrics, and Lin annotated the lyrics that include all the little details about what he was thinking or just little references. Everyone in the cast is highlighted, and it contains wonderful behind-the-scenes photos. Before the pandemic, everyone who came over to record with me signed my Hamiltome. It is one of my most prized possessions, and I unfortunately haven't been able to keep it up since 2020. For example, Jonathan Groff is not in my Hamiltome for that reason. But for those pre-pandemic episodes, it was a living, breathing entity. It is the coolest guest sign-in book. It was a very beautiful way to commemorate people who appeared on the podcast.

Do you have a favorite Hamilton moment that you feel comfortable sharing?
One of the coolest experiences I have had was sitting in the orchestra pit. The space is so teeny, tiny and I felt like I was in the way. I'm such a fan girl for musicians and to be right there, it was a magical moment. That type of access is a luxury, and I certainly do not take it for granted.

What advice would you give 2015 Gillian based on all the knowledge that you have gained since started The Hamilcast and subsequently your podcasting career? 
Perfection is the enemy of the good. If you wait for something to be a perfectly polished, then you will never finish it and you will keep chasing that perfection. I worked in a toxic environment as one of my freelance gigs right when I started the Hamilcast. This job was right next to Trinity Church, which is where many Hamilton-related people are buried (including Alexander Hamilton, Eliza, Angelica, and Hercules Mulligan). One day, the job became too intense, and I just decided to leave. I walked out of my job without a plan because I just needed to get out of that environment. I was drawn to Trinity Church, which I had been walking by each day on my way to work. I was reminded of the words of Hercules Mulligan, because when they knock me down, I get back up again. I didn’t have a plan, and I didn’t know where my next paycheck was coming from. I don't know how I'm going to make rent, but I have this one podcast, and I guess we'll see what happens. It was terrifying to jump without a net. I ended up getting some other freelance gigs, and then True Crime Obsessed exploded. You don't have to be next to Trinity Church asking Angelica what to do next, but it helped.

This question is for fun, and it is from my husband Robbie Rozelle. If the Schuyler sisters were part of The Real Housewives, what would their taglines be?
Love this question. The series would be either The Real Housewives of Lower Manhattan or The Real Housewives of New York Harbor. Angelica must say “Putting women in the sequel work,” right? Eliza, if she is going to be saucy Eliza, she could literally just say, “I hope that you burn” or “I'm putting myself in the narrative.” And Peggy would have to be something about how she's “more than meets the eye,” or a play on "she's not just Peggy," like “and Peggy is here to work” or something.

What are some last words for our readers and your listeners?
I want to thank everyone who has appeared on the show to tell their story. Everyone's been incredibly generous, especially pre-lockdown, where they agreed to record on their one day off and talk about their job. I'm just so grateful that people were so open and trusted me to take care of them.

For the people who saw what I was doing and got it, I will be eternally grateful that you knew that I wasn't just some fan girl who just wanted to talk to people about Hamilton. The Patreon peeps, many of whom have been there since day one, are the best community in the world and they are so warm and so generous. They've also traveled all around the world to be friends with each other independent of the podcast.

When Tommy Kail came over the first time, and I will never forget this for as long as I live, he made me cry at the end of the show. At the end of his recording, he looked right at me, and he said, “We made the show for you” and I started to cry. He said, “No, but really, we didn't know you, but we made the show for you because you took what we were beaming out and you received it in this way, and then you made this thing.” I have taken that with me, and it has meant so much to me. Now I'm at a place where I'm saying those words back to everyone. I've made a show for everybody, and part of the reason I did it for so long is because I knew that it was a comfort to people, and people loved the show.

Hamilton fans are now following all the different companies. It is like collecting baseball cards or Pokémon and they want to see every iteration of the show or every cast. They want to see the understudies and the different ensembles. The fandom is electric and ongoing.

I'm beyond grateful every day for how Hamilcast has changed my life. It has been an honor to do it for a full decade and 500 episodes. I'm very proud of it and it has been the thrill of my life. It means the world to me.

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All 500 episodes of The Hamilcast is available wherever you get your podcasts. Visit thehamilcast.com.