
The smash hit musical Hamilton is now in a movie theater near you. But in the decade since it came out, Hamilton — and much of Obama-era culture — is feeling a little dated.
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Sean Rames
Hamilton is turning. Hamilton, if you're the one person who doesn't yet know what this show is about, here's a synopsis.
Daniel Pollock Pelzner
So Hamilton is the story of an orphan in the Caribbean, born in the 1750s, who comes to the United States to make his name and fortune, helps to lead his country through the Revolutionary War and get appointed Secretary of Treasury in the new country. Treasury.
Sean Rames
Let's go.
Daniel Pollock Pelzner
And then in Act 2, it all falls apart. Tries to set up an economic plan.
Lin-Manuel Miranda
I can't stop till I get this.
Daniel Pollock Pelzner
Plan through Congress and gets mired in a financial scandal that becomes a sex scandal at his own house. Damn. And he's so embroiled in partisan rancor that he ends up getting shot in a duel by his enemy.
Sean Rames
To celebrate a decade, Hamilton is in movie theaters across the United States for the very first time. And to celebrate on Today explained from Vox, we're gonna ask if this play is now cringe. Support for the show comes from ServiceNow. AI is only as powerful as the platform it's built into, don't you know? That's why it's no surprise that more than 85% of the Fortune 500 use the ServiceNow AI platform. Didn't know that. While other platforms duct tape tools together, ServiceNow seamlessly unifies people, data workflows and AI connecting every corner of your business. And with AI agents working together autonomously, anyone is and any department can focus on the work that matters most. I've Never met an AI agent. Learn how ServiceNow puts AI to work.
Lin-Manuel Miranda
For people@servicenow.com Support for this show comes from Robinhood. Wouldn't it be great to manage your portfolio on one platform? With Robinhood, not only can you trade individual stocks and ETFs, you can also seamlessly buy and sell crypto at low costs. Trade all in one place. Get started now on Robinhood Trading. Crypto involves significant risk. Crypto trading is offered through an account with Robinhood Crypto, llc. Robinhood Crypto is licensed to engage in virtual currency business activity by the New York State Department of Financial Services. Crypto held through Robinhood Crypto is not FDIC insured or civic protected. Investing involves risk including loss of principal. Securities trading is offered through an account with Robinhood Financial, LLC MemberCIPIC, a registered broker dealer.
Daniel Pollock Pelzner
And the world's gonna know your name.
Nate Jones
What's your name, man?
Daniel Pollock Pelzner
I'm Daniel Pollock Pelsner. I teach English and theater at Portland State University, and I'm the author of Lin Manuel Miranda the Education of an Artist.
Sean Rames
How much time have you spent in the last several years thinking about Hamilton?
Daniel Pollock Pelzner
God, this feels like that, like, meme about how often do you think about the Roman Empire? Daily.
Sean Rames
Kind of hard to avoid this phenomenon for the past 10 years. But the musical is 10, of course, and the streaming version of Hamilton is five. But now that's coming to theaters for the first time. And that's why we have an excuse to talk about how this musical feels different in 2025 than it did in 2015. Your thoughts?
Daniel Pollock Pelzner
So Hamilton has these two acts, and I felt like we got to live in Act 1 Hamilton for a while, where we had this hope of a country that was welcoming immigrants into a coalition that was going to dream of a better future. And for the last few years, I feel like we've been living in Act 2 Hamilton, which is. Is it all going to fall apart? Are we going to become so polarized that we end up in a state of political violence? And is everything that got built before going to collapse?
Sean Rames
Where did this even come from? Before we talk about the politics.
Daniel Pollock Pelzner
So lin Manuel Miranda, 28 years old, won a Tony Award for his first musical, in the Heights, and takes a vacation in 2008. And he's a fast reader, so he brings along one really big book to sustain him on vacation, which is Ron Chernow's biography of Alexander Hamilton. And as he is lying on a hammock in the beach above Playa del Carmen, he. He tells me that he has these, like, three insights. Number one, one is he didn't know that there was a founding father who was born outside the continental US in the Caribbean.
Lin-Manuel Miranda
He was sort of our proto immigrant story. I mean, really came here on a scholarship to get his education and ended up shaping the world.
Daniel Pollock Pelzner
And Hamilton's own journey from impoverished orphanhood on this little island to becoming an architect to the American government reminded Lin Manuel of his own F, who was born in Puerto Rico, got a scholarship to come to nyu, and became an important political figure in New York and national politics. So he starts to envision the parallels between Hamilton's story and the world he lives in. Number two. And his second insight is that Hamilton's story is a hip hop story.
Lin-Manuel Miranda
It's got everything. It's got sex, it's got politics, it's got genius.
Daniel Pollock Pelzner
The rise of a wordsmith from humble beginnings to making a name for himself and turning his own impoverishment into success is a story that mirrors the 90s Hip hop artists that Lin Manuel grew up loving, Biggie and Tupac especially, and that Hamilton shared their ultimate faith of pissing people off and getting shot. And then the third insight was that this show Lin Manuel originally conceived of as a concept album, like musicals like that would be sung through on a record. And he got started and he premiered what became the first number of the show at the invitation of the White House in the East Room 2009.
Lin-Manuel Miranda
I'm actually working on a hip hop album. It's a concept album about the life of someone I think embodies hip hop. Treasury Secretary Alexander Hamilton. You laugh, but it's true.
Daniel Pollock Pelzner
And over the next six years, builds up the whole arc of Hamilton's life with his collaborators and opened in 2015.
Sean Rames
How big did this show get? When was Peak Hamilton? I think it's coming past. Yeah.
Daniel Pollock Pelzner
Well, it just keeps getting bigger. I mean, it started as a kind of, I would say, elite cachet phenomenon, where celebrities and political leaders were bragging that they could get what were scalped with very expensive tickets.
Lin-Manuel Miranda
The best seat in the house at.
Daniel Pollock Pelzner
Current right now will take you back.
Nate Jones
Almost $900 a pop.
Sponsor/Ad Voice
I paid $725 for my ticket.
Nate Jones
But the musical, doubling the number of.
Daniel Pollock Pelzner
$10 tickets it's making available via same day lotteries. But by the time the cast recording came out in the fall of 2016, it became a mass phenomenon and the album was on top of the Billboard charts. And this week, Hamilton became the first.
Sponsor/Ad Voice
Cast recording to spend 500 weeks on.
Daniel Pollock Pelzner
The Billboard 200 record charts.
Lin-Manuel Miranda
Taken Broadway by storm, captivating the entire.
Nate Jones
Country, winning tons of awards. Turn musical haters into die hard fans.
Daniel Pollock Pelzner
It was even on top of the rap charts. The show won all the awards, the Tony's Grammy, Pulitzer Prize. And it became a conversation beyond even Broadway geeks like me. So that people who just cared about American culture more broadly and how we tell American stories had an opinion about the show.
Sean Rames
Okay, now let's talk about how for a while it felt like we were living in the act. One of Hamilton. How directly was this show entwined with the Obama administration and the promise of hope for America?
Daniel Pollock Pelzner
It was pretty intimately connected, Sean. So not only was the White House the venue for the initial performance of.
Nate Jones
The first number, this is definitely the room where it happened right here.
Daniel Pollock Pelzner
But Obama's own speeches helped to create a kind of template for some of the show's musical numbers. So Lin Manuel loved the way that Will I Am of the Black Eyed Peas set Obama's yes we can speech to music and turned it into a music video. Yes, we can. It's opportunity, prosperity. Miranda thought that would Be a cool way to musicalize George Washington's farewell address.
Lin-Manuel Miranda
After 45 years of my life dedicated to its service with an upright zeal.
Daniel Pollock Pelzner
And he even got Obama to record a cover of George Washington's Number One last time after he left the White House.
Lin-Manuel Miranda
The faults of incompetent abilities will be consigned to a oblivion, as I myself must soon be to the mansions of rest.
Daniel Pollock Pelzner
So it was pretty intimately connected to the world of the Obamas, even as it had a lot of shout outs and parallels to earlier historical and musical eras.
Sean Rames
We should point out, though, that it wasn't just the left who enjoyed this show. Obama famously said, in fact, Hamilton, I'm.
Nate Jones
Pretty sure is the only thing that.
Lin-Manuel Miranda
Dick Cheney and I agree on.
Daniel Pollock Pelzner
That's true. Dick and Lynn Cheney both praised the show. George W. Bush likened himself to Hamilton in a wonderful documentary about the musical. And the Clintons and the Bidens were coming, too. So it became the show to see, and a show into which a lot of people could read their vision of America. Whether that was a kind of more traditional narrative of a country where you could pull yourself up by your bootstraps and sort of vision of a meritocracy, or whether that was even a slightly more radical vision where black hip hop artists are quoting from the Black Lives Matter movement, trying to make this Black.
Lin-Manuel Miranda
Lives Matter a movement. Not a moment. This is not a moment.
Daniel Pollock Pelzner
It's the movement calling for people to rise up and, you know, using the kind of counter establishment language of hip hop to envision a new America.
Sean Rames
How does it turn and when does it turn?
Daniel Pollock Pelzner
Lin Manuel Miranda had done fundraisers for the Democratic Party in the run up to the 2016 election. But the real tipping point came, I think, after the election, when Vice President elect Mike Pence came to see the show on Broadway. Miranda, along with his producers and director, decided to write a speech for the actor playing Aaron Burr at the time, Brandon Victor Dixon, to give after the show, in which Dixon said to Mike Pence, who was sort of leaving the lobby at the time, that we, sir.
Lin-Manuel Miranda
We are the diverse America who are alarmed and anxious that your new administration will not protect us. But we truly hope that this show has inspired you to uphold our American values and to work on behalf of all of us.
Sean Rames
Even that feels kind of dated like that anyone thought that that would work, right?
Daniel Pollock Pelzner
Perhaps that is the fantasy of musical theater, that we can all come together for a curtain call. Pence was fine with it. But the next morning, Trump started tweeting that the cast had been Very rude to Pence, that Hamilton was overrated, that Hamilton needed to apologize. And in the wake of that, the show started to get security threats from MAGA supporters. One even interrupted a show in Chicago. And from then on, it really became the kind of counter Trump show. So then the latest chapter in the saga is that Hamilton was supposed to have an upcoming performance at the Kennedy center in Washington, D.C. but after Trump got rid of all of the Democratic members of the Kennedy Center's board, Miranda and his producers pulled their show, saying that they didn't want Hamilton to appear at a Trump puppet venue.
Sean Rames
Has Trump seen Hamilton? Do we know?
Daniel Pollock Pelzner
Not that I know of. I think his favorite show is Evita, a show that has nothing to do with the rise of populist fascism and stardom in service of authoritarian government.
Sean Rames
That was a joke. I like jokes. Has the effectiveness of the message of Hamilton dwindled over time?
Lin-Manuel Miranda
Back when I was just a little baby boy from Queens, I was just a founding father from 1893.
Sean Rames
Whether it's people of color playing these.
Nate Jones
White colonists or not, it's still a.
Sean Rames
Story about white colonists and trying to sympathize with them. I'm not doing that.
Nate Jones
Some guy with an undercut just called me Soy boy. Oh, don't worry, Greg. It's a nice, safe space where you don't have to pretend to like Hamilton. Well, I like Hamilton.
Sean Rames
Sure you do.
Nate Jones
We all do.
Sean Rames
I just wonder, like, over time, has Hamilton come to feel kind of cringe to people, too hopeful, too in love with the United States and the American project?
Daniel Pollock Pelzner
I mean, man, the things that feels most dated about it to me, Sean, is the notion that having a sex scandal would ruin your political prospects. But when I return to this show, what really strikes me is that it's a tragedy. It's set up from the start of how did this horrible thing happened, which is that one friend and political rival murdered another one. And that tragedy hangs over the whole show. And so when I see it, I guess I see less this kind of celebration of America and more a sense of how quickly the American dream can fracture. One thing I keep remembering, Sean, is that the show starts with a question.
Lin-Manuel Miranda
How does a bastard orphan, son of.
Sean Rames
A whore and a Scotsman drop in the middle of a forgotten spot in the Caribbean by Providence, impoverished and squalor.
Nate Jones
Grow up to be a hero and a scholar?
Daniel Pollock Pelzner
And it ends with a question. And I don't think this show provides a single answer to those questions. I think it leaves those as open questions, and they're questions that are open for us in America today.
Sean Rames
Lin Manuel Miranda the Education of an Artist. That's the name of Daniel Pollock Pelzner's new book. It's out next week. Hamilton is in theaters right now. If you're looking to kill three hours with some open questions about America this weekend. And maybe Hamilton isn't cringe, but some Obama corps culture certainly is. We'll discuss next on today. Explain.
Lin-Manuel Miranda
Wait for it.
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Daniel Pollock Pelzner
Support.
Sponsor/Ad Voice
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Lin-Manuel Miranda
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Sean Rames
Today explained that. Today explained that. Today Explained. Today explained. Sean Ramis from here with Nate Jones, who's a feature writer at New York Magazine and Vulture and not so long ago, one who wrote about something called Obama Corps. Is that right, Nate, for Vulture?
Nate Jones
Yes, yes, indeed. It was last August 2024, which, you know, only a year ago, but perhaps longer than that emotionally.
Sean Rames
Right. And what exactly is Obama Corps? For those who have never heard the term?
Nate Jones
I mean, Obama Corps is the pop culture and the general culture that was sort of spurred by Obama's election. It was an outpouring of positivity and a belief that the future would always be as good as the present and a belief in institutions and just kind of a general idealism and a sincerity and an earnestness that was kind of born out of the sense that, yeah, the arc of history was always bending towards justice. And we'd kind of arrived at, at this sort of key marking point and things are just going to keep getting better from there. And obviously, you know, that didn't happen. And so now when we look back on it with the distance of 10 to 15 years, I think it causes a lot of hurt feelings and mixed emotions and embarrassment.
Sean Rames
And is Hamilton like the apotheosis of Obama Corps?
Nate Jones
Yeah, I mean, I think Hamilton in many ways has become the single cultural object that most stands in for the Obama era as a whole. A few weeks ago, people started sending around an old 2016 Onion HUD line that said DNC aiming to reconnect with working class Americans with new Hamilton inspired Lena Dunham web series, which it became a stand in for this proudly cosmopolitan, optimistic, triumphant era in American life.
Sean Rames
What else? What do we think of when we think of Obamacore? What else fits into the genre?
Nate Jones
Last summer when we wrote the list, we had 100 things on the list. And that a hundred. The original was 200 or 300.
Sean Rames
Give us the top 10 in your heart.
Nate Jones
Okay, the top 10 millennial pink girl Bosses, Stomp and Holler bands, Glee, Louis C.K. female Ghostbusters, Taylor Swift, Swift's 1989 era, the word mansplaining, the TV show Transparent and then the 10th one is an Instagram filter of a woman with bangs drawing a mustache on her finger and putting it in front of her face.
Sean Rames
Is that like, definitely. Like a Nate Jones number one right there.
Nate Jones
That was a late cut. That was the 101st one.
Sean Rames
How many of these things are you comfortable calling Cringe now? Not of those 10, but, like the whole hundred.
Nate Jones
I mean, a lot of it is. I mean, it's hard, right? Because a lot of this stuff, you don't wanna write the whole thing off. Right. Like, moonlight is Obamacore in a way. Right. And Moonlight's an amazing film.
Sean Rames
Moonlight holds up.
Nate Jones
Yeah. You know, and a lot of the. I'd say a lot of the music really holds up. You know, some of those Miley Cyrus songs from the Bangers era, they hold up.
Lin-Manuel Miranda
I came in like a wrecking Ball.
Nate Jones
Taylor Swift songs, you know, 1989, good album. This sick Be something that we've seen recently. I don't know if you remember, but a few weeks ago, there was a whole week of discourse about the Edward Sharp and the Magnetic Zero song Home.
Lin-Manuel Miranda
Alabama, Arkansas, I show love my mom pop, not the way that I do love you.
Sean Rames
And people are saying, like, this is actually really bad.
Daniel Pollock Pelzner
Worst song ever made.
Sponsor/Ad Voice
I would respect him more if he just went ahead and started the yoga sex cult he clearly wants to.
Nate Jones
Primarily, it is guilty of sounding like.
Sean Rames
Something that was composed to be played.
Nate Jones
While someone is being euthanized. But that's true of most pop music. Yes. Yes. And I think, you know, and in this discourse, a lot of people made the point that, like, right, we have what's called the nostalgia cycle. And it kind of is generally like, you know, when something's a year ahead of its time, it looks really cool. When something's a year behind its time, it's kind of. You're kind of tired of it. When something is 20 years behind the times, it gets cool again. But when something is 10 to 15 years, that is kind of the nadir of the sine curve of coolness. And I think with a lot of this Obama era culture, we are kind of just at the nadir of the coolness in the nostalgia cycle. Right. Like, we are already seeing people starting to bring back the early to mid 2000s. Right. Like you look at Saltburn, that's very much nostalgia for the mid 2000s. So we probably are like five to 10 years before someone tries to bring the Obama corps stuff back. But until then, yeah, it's kind of just. It's people in their late 30s thinking back on the culture of their early 20s.
Sean Rames
And reassessing it.
Nate Jones
And reassessing it. Yes. And then I think the thing that specifically works with Obama Corps is that there was this major thing that happened at the end of it, and it broke a lot of people's brains, because one of the fundamental elements of Obama corps was a confidence. It was a confidence that the culture was on our side and that things would keep getting better. And then that didn't happen. That was proven decisively wrong, you know, in 2016. And then elements of Obama corps, I would say, still sort of survived the election of Trump in 2016, the first election. You know, I think a lot of the social elements really sort of found their full flower. Right. The social movements that came along with Obama's election, if anything, they were heightened. Right. Trump is when we saw MeToo, you know, that is when we saw a wider acceptance of the Black Lives Matter movement and everything. But then I think now in the second Trump era, even those social movements have kind of. I don't want to say died like they've been killed. Right. Like, there has been a decisive conservative backlash that has. That has attempted quite successfully to snuff that out. And so everything is kind of being reincessed.
Sean Rames
In preparation for this interview, I was thinking about how Chance the Rapper is kind of Obama core, 100% or, like, really Obama core.
Nate Jones
He is one of the defining artists. Yeah.
Sean Rames
Because here's a rapper whose, like, father literally worked with Barack Obama, but also just exuded positivity and kindness. He came from Chicago, and it just reminded me of this video of him performing at the White House for, like, their holiday, you know, maybe tree lighting ceremony. Sasha, Obama's there, like, singing lyrics to Sunday Candy, which is a song, I should add, about going to church with your grandmother. Like, not exactly left right stuff here.
Nate Jones
Yeah.
Sean Rames
But everyone's smiling if it feels, like, pure and decent, and it doesn't feel like something we should be embarrassed of. If anything, it feels like a president celebrating the arts and the holidays and family and religion and love, and you just wonder if we could get back there one day.
Nate Jones
I agree. Exactly what you were saying about Chance the Rapper, you mentioned purity, and I think that was definitely part of it. There was a longing to go back to this kind of purity of childhood. In a lot of it, you look at Chance, you know, rapping over the theme song to Arthur, the children's TV.
Lin-Manuel Miranda
Show, every day when you're walking down the street. Wonderful. Everybody that you meet has an original point of view.
Nate Jones
There was a sense that, like, oh, if we could all kind of just embrace our inner child, that is what we all need. And obviously that has definitely kind of gone away. But yeah, no, I mean, it's. Yes, I would love to be hopeful that we can have an era like that again and that it won't just all be nihilism and cynicism.
Sean Rames
Nate Jones. You can check out the big Obama Corps package he worked on@vulture.com Abhishai Artsy made our show today. Jolie Meyers edited, Laura Bullard checked the facts and David Tadashore mixed. The rest of our team includes Patrick Boyd, Denise Guerra, Hadi Mwagdi, Miles Bryan, Peter Balanon Rosen, Devin Schwartz, Rebecca Ybarra, Danielle Hewitt and Kelly Wessinger who joined us this week. Welcome Kelly. We used music by Breakmaster Cylinder. Amen. Al Asadi is our supervising editor. Miranda Kennedy's our executive producer Noel King is in the middle of a forgotten spot in the Caribbean and Today Explained is distributed by wnyc. The show is a part of the Vox Media Podcast network. You can check out more of our shows@podcasts.voxmedia.com and you can listen to this show without ads by signing up to Support us@vox.com members. When you guys were compiling your list, did you determine whether or not Vox was ObamaCorp?
Nate Jones
Vox is 100% ObamaCorp and the only reason we did not put it in was to be good corporate siblings. Vox is the ultimate of Obama Corps. It is the right, the element of Obama Corps that is it's a culture by and for rule followers. Right? It's kids who sat in the front of the class. It's people who thought that we could get a better future by having the right charts. And I'm not saying that insultingly like I believed it too. I thought the right chart would make a difference and you know, turns out it didn't.
Sean Rames
I'm sending this to Ezra.
Lin-Manuel Miranda
Olivia loves a challenge. It's why she lifts heavy weights and likes complicated recipes. But for booking her trip to Paris, Olivia chose the easy way. With Expedia, she bundled her flight with a hotel to save more. Of course, she still climbed all 674 steps to the top of the Eiffel Tower. You were made to take the easy route. We were made to easily package your trip. Expedia made to travel flight inclusive packages are atoll protected.
Date: September 5, 2025
Hosts: Sean Rameswaram, Noel King
Guests: Daniel Pollock Pelzner (Portland State University, author), Nate Jones (New York Magazine/Vulture)
Main Theme: Examining how "Hamilton" fits into the cultural era dubbed “Obamacore,” and questioning whether both have become "cringe" in 2025.
The episode explores the legacy of the musical "Hamilton" on its 10th anniversary, analyzing its cultural and political impact, the changing public perception over a decade, and its inseparable connection to the Obama presidency and the optimism of the era. In the second half, the discussion broadens into "Obamacore"—the pop culture and prevailing spirit of the Obama era—interrogating why some of its once-celebrated icons and trends are now viewed with embarrassment or nostalgia, and what that says about where America stands today.
Summary of the Musical:
Daniel Pollock Pelzner summarizes "Hamilton" as the immigrant-to-icon story of Alexander Hamilton, covering his instrumental role in the Revolutionary War and the formation of America’s financial system, his fall amid partisan rancor and scandal, and his ultimate death in a duel.
"So Hamilton is the story of an orphan in the Caribbean, born in the 1750s... who comes to the United States to make his name and fortune, helps to lead his country through the Revolutionary War and get appointed Secretary of Treasury..." — Daniel Pollock Pelzner [00:07]
Miranda’s Three Insights:
“[Hamilton] was sort of our proto immigrant story. I mean, really came here on a scholarship to get his education and ended up shaping the world.” — Lin-Manuel Miranda [04:11] “[Hamilton’s] story is a hip hop story... The rise of a wordsmith from humble beginnings... mirrors the 90s Hip hop artists that Lin Manuel grew up loving..." — Daniel Pollock Pelzner [04:49]
“It became the show to see, and a show into which a lot of people could read their vision of America.” — Daniel Pollock Pelzner [08:58]
Political Symbiosis:
“Obama’s own speeches helped to create a kind of template for some of the show's musical numbers.” — Daniel Pollock Pelzner [07:44]
Inclusivity as a Universal American Dream:
The musical allowed both conservatives and liberals to project their ideals onto its story, from “bootstraps” meritocracy to the radical possibilities of recasting American history.
“Obama famously said, in fact, Hamilton, I'm pretty sure is the only thing that Dick Cheney and I agree on.” — Sean Rames [08:49]
Black Lives Matter Connections:
Through hip hop and contemporary castings, "Hamilton" foregrounded then-current movements.
“Black Lives Matter a movement. Not a moment. This is not a moment.” — Lin-Manuel Miranda [09:32]
Post-2016 Shift:
“The real tipping point came after the election, when Vice President elect Mike Pence came to see the show… in which Dixon said... ‘we, sir, are the diverse America who are alarmed and anxious that your new administration will not protect us...’” — Daniel Pollock Pelzner [10:22]
Erosion of Fantasy:
Pelzner reflects on the futility of believing in musical theater’s power to unite in post-2016 America.
“Perhaps that is the fantasy of musical theater, that we can all come together for a curtain call.” — Daniel Pollock Pelzner [10:46]
Reassessment:
“The thing that feels most dated... is the notion that having a sex scandal would ruin your political prospects.” “I see less this kind of celebration of America and more a sense of how quickly the American dream can fracture.” — Daniel Pollock Pelzner [12:35]
Bookends of Open Questions:
“It ends with a question. And I don't think this show provides a single answer... They're open for us in America today.” — Daniel Pollock Pelzner [13:33]
Guest: Nate Jones, author of the “Obamacore” list at Vulture
Definition:
“Obamacore” is the pop and general culture marked by optimism, faith in institutions, and an earnestness fueled by the belief that history bends toward justice—emblematic of emotions after Obama’s election and dominance in the early 2010s.
“It was an outpouring of positivity and a belief that the future would always be as good as the present... and obviously, you know, that didn’t happen.” — Nate Jones [18:05]
Hamilton as Obamacore’s Pinnacle:
“Hamilton in many ways has become the single cultural object that most stands in for the Obama era as a whole.” — Nate Jones [18:58]
Obamacore’s Iconography:
“The original was 200 or 300. Give us the top 10 in your heart…” — Nate Jones [19:41]
Cringe Factor & Nostalgia Cycle:
“When something is 20 years behind the times, it gets cool again. But when something is 10 to 15 years, that is kind of the nadir of the sine curve of coolness.” — Nate Jones [21:27]
Cultural Disillusion:
The shock of 2016 “broke a lot of people’s brains,” upending faith in inevitable progress, and leading to reassessment or embarrassment about prior optimism.
“One of the fundamental elements of Obamacore was a confidence... And then that didn't happen. That was proven decisively wrong, you know, in 2016.” — Nate Jones [22:31]
Endurance and Hope:
“A lot of this stuff, you don't wanna write the whole thing off... Moonlight holds up.” — Nate Jones [20:28]
Case Study:
Chance the Rapper as embodiment of Obama-era hope: positivity, family values, and connection to Obama (his father worked for Obama).
“If anything, it feels like a president celebrating the arts and the holidays and family and religion and love, and you just wonder if we could get back there one day.” — Sean Rameswaram [24:49]
Desire for Lost Innocence:
The longing for “purity of childhood” in the earnestness of Obama-era culture.
“There was a sense that if we could all kind of just embrace our inner child, that is what we all need. And obviously that has definitely kind of gone away.” — Nate Jones [25:16]
“Vox is 100% ObamaCorp and the only reason we did not put it in was to be good corporate siblings. Vox is the ultimate of Obama Corps... a culture by and for rule followers. It's kids who sat in the front of the class. It's people who thought that we could get a better future by having the right charts.” — Nate Jones [26:48]
On Hamilton’s Tragedy:
“It’s set up from the start of how did this horrible thing happened, which is that one friend and political rival murdered another one. And that tragedy hangs over the whole show... more a sense of how quickly the American dream can fracture.”
— Daniel Pollock Pelzner [12:35]
On the Fragility of Progress:
“One of the fundamental elements of Obama corps was a confidence... that the culture was on our side and that things would keep getting better. And then that didn't happen. That was proven decisively wrong, you know, in 2016.”
— Nate Jones [22:31]
On the Nostalgia Cycle:
“When something is 20 years behind the times, it gets cool again. But when something is 10 to 15 years, that is kind of the nadir of the sine curve of coolness.”
— Nate Jones [21:27]
On Vox’s Place:
“Vox is 100% ObamaCorp... It's people who thought that we could get a better future by having the right charts. And I'm not saying that insultingly—like, I believed it too.”
— Nate Jones [26:48]
The episode blends critical nostalgia with a wry, self-aware tone. The guests balance academic insight, pop culture savvy, and personal reflection, threading humor and wistfulness while examining the intersection of politics, art, and generational self-image.
The episode situates "Hamilton" as both a mirror and maker of the Obama era’s optimism—a cultural artifact that, like the political moment that birthed it, now finds itself in the awkward middle-ground between embarrassing relic and enduring inspiration. Through the lens of “cringe” and the nostalgia sine wave, the conversation offers not just a reassessment of a decade’s worth of culture but a meditation on the volatility of hope, memory, and American identity.