Today, Explained — "Hamilton and Obamacore Cringe"

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.

Episode Overview

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.

Key Discussion Points & Insights

1. Hamilton’s Origin and Rise

• 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 as a proto-immigrant story mirroring Miranda's own family.
  • Hamilton’s biography as a "hip-hop story"—the wordsmith outsider remaking himself, akin to Biggie or Tupac, and meeting a violent end.
  • The concept album genesis and its first performance at the Obama White House.

  “[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]

2. Peak Hamilton and Mass Phenomenon

• Trajectory:
  Starts as an elite sensation, then explodes in popularity, with sold-out shows, high ticket prices, mass lotteries, and a record-breaking cast album.
  • The show garners Tonys, a Grammy, and a Pulitzer, and is praised by figures across the political spectrum (e.g., Obama, Dick Cheney, George W. Bush, the Clintons, Bidens).

  “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]

3. Hamilton and the Obama Era

• Political Symbiosis:

  • Deep ties to the Obama administration’s ethos of hope and integration.
  • The show's style and themes reflect and draw inspiration from Obama’s messaging, most notably the use of music and rhetoric paralleling “Yes We Can.”

  “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]

4. The Turn: From Optimism to Division

• Post-2016 Shift:

  • The famed post-show address to Mike Pence introduced a divisive turn, leading to Trump’s (and some public’s) backlash.
  • "Hamilton" became seen as aligned with anti-Trump, liberal resistance.

  “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]

  • Trump’s response ("overrated," demanding an apology) heightened polarization and shifted "Hamilton’s" symbolic meaning.

• 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]

5. Is Hamilton “Cringe” in 2025?

• Reassessment:

  • Does the musical now feel too earnest, too in love with America?
  • Pelzner contends the show is more tragedy than celebration, highlighting the fragility of the American project and democracy.

  “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:

  • The show opens and closes with unresolved questions, mirroring present-day uncertainties.

  “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]

6. Obamacore: Defining and Dissecting an Era

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:

  • The musical stands as the ultimate artifact of this era’s cosmopolitan optimism.

  “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:

  • Nate’s “Top 10” Obamacore symbols: Millennial pink, Girl Bosses, Stomp & Holler bands, Glee, Louis C.K., Female Ghostbusters, Taylor Swift (1989), “Mansplaining,” Transparent, and quirky Instagram filters.

  “The original was 200 or 300. Give us the top 10 in your heart…” — Nate Jones [19:41]

• Cringe Factor & Nostalgia Cycle:

  • Examines why elements of Obamacore now produce embarrassment.
  • The “nadir of the nostalgia cycle” is about 10–15 years after the fact—when things look most out-of-step and embarrassing, waiting to be revived by a later wave.

  “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:

  • Not everything is dismissed—some cultural landmarks hold up (“Moonlight,” Taylor Swift’s 1989, etc.), and nostalgia may again revive these trends.

  “A lot of this stuff, you don't wanna write the whole thing off... Moonlight holds up.” — Nate Jones [20:28]

7. Obama-Era Purity: Chance the Rapper and Beyond

• Case Study:
  Chance the Rapper as embodiment of Obama-era hope: positivity, family values, and connection to Obama (his father worked for Obama).

  • Example: Chance performing "Sunday Candy" at the White House, representing purity and uplift through the arts and community.

  “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]

8. Is Vox ObamaCore?

• Meta-Reflection:
  Nate Jones acknowledges Vox as “the ultimate of Obama Corps”—a culture of hopeful rule followers who believed better information (and charts) could drive social progress.

  “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]

Notable Quotes & Memorable Moments

• 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]

Timestamps for Key Segments

• Hamilton’s origin and Miranda’s vision: [00:07] – [04:49]
• Hamilton’s popularity and awards: [06:00] – [07:15]
• Hamilton and the Obama White House: [07:15] – [08:33]
• Political spectrum embrace of Hamilton: [08:42] – [09:45]
• The Pence incident and Trump era: [09:47] – [11:48]
• Reevaluation: Is Hamilton cringe? [12:09] – [13:33]
• Transition to Obamacore discussion with Nate Jones: [17:22]
• What is Obamacore? [18:05] – [19:35]
• Top 10 Obamacore icons: [19:35] – [20:16]
• Cringe factor & nostalgia cycle: [20:28] – [22:31]
• Obama era’s “purity” (Chance the Rapper): [23:40] – [25:43]
• Vox as ObamaCore meta-commentary: [26:48]

Tone

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.

Conclusion

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.