The New Yorker Radio Hour – Episode 31: Larry Wilmore on Presidential Comedians, and James O’Keefe’s Blunder

Date: May 20, 2016
Host: David Remnick
Featured Guests: Larry Wilmore, Jane Mayer, James O’Keefe, Hua Hsu, David Carroll, Jen Spira/Rachel Dratch, Brian Silverman, Elizabeth Samet

Overview

This episode explores three major stories, blending humor, politics, investigative journalism, and thoughtful profiles:

1. Larry Wilmore on Race, Humor, and Presidential Comedy:
   David Remnick interviews comedian Larry Wilmore about his memorable appearance at President Obama's final White House Correspondents’ Dinner, presidential comedic personas, and the racial undertones of the 2016 election.

2. James O’Keefe’s Blunder:
   Jane Mayer recounts an attempted sting operation by conservative activist James O’Keefe against the Open Society Foundations—an operation that backfired due to an accidental voicemail.

3. Veterans at Vassar: David Carroll’s Story:
   Hua Hsu profiles David Carroll, an Army veteran navigating campus life at the liberal Vassar College, showing the intersections of war, identity, and the challenges of reintegrating.

The episode also touches briefly on the meaning of leadership at West Point, and features a satirical commencement speech by Jen Spira.

1. Larry Wilmore: Presidential Comedy & Race in America (00:30 – 15:03)

Main Discussion Points

• Wilmore at the 2016 White House Correspondents’ Dinner:
  Wilmore discusses crafting his set, feeling the room's shifting energy, and the intent behind jokes—especially those about Obama and Wolf Blitzer. He reflects on the tension of balancing comedy with cultural and political commentary.

• The Infamous Closing Remark:
  Wilmore recounts the powerful, controversial closing where he addressed President Obama with, "Yo, Barry, you did it. My nigga did it." He explains that it was a deeply personal moment, meant to express pride in Obama’s presidency as a Black American.

  • Quote: “To me, that was having a private moment in public.” (Larry Wilmore, 04:49)

• Obama’s Humor and Delivery:
  The pair analyzes Obama’s comedic timing, comparing him to past presidents—Reagan, Nixon, Bush—concluding that Obama is rarely, if ever, unintentionally funny.

  • Quote: “Obama uses his smile and his charm as his cigar, if you will.” (Wilmore, 07:32)

• Presidential Comedic Styles:
  Wilmore discusses which presidents were naturally funny and how charisma often fuels the perception of humor.

  • “Ronald Reagan was very funny. Reagan was funny on purpose and by accident. Obama’s never unintentionally funny, which is interesting.” (Wilmore, 09:59)

• Trumpism as Backlash:
  Wilmore calls Trump’s campaign “the unblackening,” seeing it as a reaction to Obama’s presidency and a reassertion of white America’s anxieties.

  • Quote: “The Trump presidency is certainly a referendum. I call it the unblackening.” (Wilmore, 11:04)
  • On “Make America Great Again”: “It appeals to this narrative that Obama has ruined the country in some way… I find that part very offensive.” (Wilmore, 11:33)

• Wilmore on Hillary Clinton, Comedy, and the Future:
  He remarks that Hillary provides “comedy in spite of herself,” and looks forward to comic material regardless of the election outcome.

Notable Quotes & Timestamps

• On the emotional weight of Obama’s presidency:
  “In our lifetime, a black man couldn’t be a quarterback. …Then to see this man… a black man’s the leader of the free world... I was crying when I wrote that down, you know, because it meant so much to me.” (Wilmore, 03:29–04:49)

• Obama’s comedic mastery:
  “He learned how to pause like comedians used to have accessories onstage… Obama uses his smile and charm as his cigar, if you will. And he’s very good at it.” (Wilmore, 07:32)

2. James O’Keefe’s Blunder (16:10 – 24:45)

Story Summary

Jane Mayer recounts the unraveling of James O’Keefe’s attempted “sting” at the Open Society Foundations (funded by George Soros). O’Keefe, under the alias "Victor Keshe," leaves a voicemail but inadvertently records a lengthy conversation plotting entrapment because he forgets to hang up.

Key Discussion Points

• The Accidental Voicemail:
  O’Keefe's failure to hang up exposes his full plan to infiltrate the foundation through low-level staff.

• Inside the Blunder:

  • They discuss setting up “compromising situations” via fake donors, referencing Soros' Hungarian heritage to build credibility.
  • O’Keefe critiques which entities "would be crass enough" to accept shady money, listing: "Hillary would. Chelsea would. Center for American Progress would." (21:25)
  • He comments that Soros’s foundation wouldn’t fall for such schemes, but others might.

• Aftermath:
  When confronted by Mayer, O’Keefe first feigns ignorance, then admits to the failed attempt and apologizes to supporters, claiming more stings are ongoing.

  • “What needs to happen is someone other than me needs to make 100 phone calls like that.” (O’Keefe on the voicemail, 24:37)

Timestamps

• Introduction and accidental recording: 16:10–18:55
• Exposed plotting and Soros targeting: 19:00–22:02
• Jane Mayer’s investigation and O’Keefe’s public reaction: 23:04–24:45

3. The Veteran at Vassar: David Carroll’s Story (25:07 – 39:33)

Main Discussion Points

• Adjustment to Campus Life:
  David Carroll, a 35-year-old Army veteran and Republican, enrolls at Vassar College. He and professor Hua Hsu reflect on culture shock and Carroll’s process of relating to much younger, liberal students.

  • “Let’s go to a woman’s college full of Democrats. Awesome.” (Carroll on choosing Vassar, 26:38)

• Intellectual and Social Challenges:
  Carroll discusses the differences in communication styles between military and academic life, learning new ways to express opinions.

  • “In the military, the more I cuss, the faster I get promoted. So that was, you know, that’s just how you talked…” (Carroll, 28:11)

• Processing Combat Experiences:
  Carroll shares his struggles with writing about war, feelings about violence, and the burden of memory—detailed in a confidential essay for Hsu.

  • “It's hard to tell my story to civilians because the first thing most of them think is he likes killing. I wonder if he still wants to…” (Carroll, 30:40)

• Music and Memory:
  He recalls listening to heavy metal, particularly “Let the Bodies Hit the Floor,” as a war soundtrack, but can’t listen to it now.

  • “If you had to put a theme song to the war in Iraq, it would be that... Now I can’t listen to them anymore.” (Carroll, 33:27–33:59)

• Post-War Identity & Politics:
  Carroll emphasizes that real differences between right and left are overblown, finding commonalities among students:

  • “The left and right aren't that far off... almost every single person here could be just categorized in the middle.” (Carroll, 37:55)

• Looking Forward:
  Upon graduating, Carroll is unsure of his next steps but intends to enjoy some peace before considering law school or other paths.

4. Satire: Commencement Speech to the Class of 2050 (39:57 – 42:57)

Highlights

• Satirical Tone:
  Jen Spira (performed by Rachel Dratch) delivers a mock-apocalyptic commencement speech, lampooning both modern career advice and the absurdity of survival in a dystopian future.

• Memorable Lines:

  • “Success doesn’t mean having a big house or a fancy corner office. There’s only one true measure of success, and that’s how close you can get to deciphering the Mayan hieroglyph that will show humanity how to defeat the tall ones.” (Spira, 41:20)

5. Leadership at West Point: Reflection & Responsibility (44:36 – 54:14)

Main Discussion Points

• Exploring Leadership:
  Josh Rothman visits West Point, speaking with English professor Elizabeth Samet and senior cadet Brian Silverman about the meaning and practice of leadership—not just crisis heroics, but daily responsibility, reflection, and character.

• Cadet Anecdote:
  Silverman shares a story of making a dangerous mistake during training (a negligent weapons discharge), and how leadership meant owning up, learning, and facing consequences.

• Key Insights:

  • “A lot of good leadership happens silently. It happens not in moments of crisis.” (Samet, 53:05)
  • “Leaders are responsible, restrained, attentive, focused, concerned, even a little frightened of the consequences of their actions…” (Rothman, 54:07)

Conclusion & Episode Takeaway

The episode weaves together comedy, political critique, investigative journalism, and personal storytelling to examine American leadership and identity—from the nation’s highest office to a liberal arts campus and the training grounds of future military leaders. In each story, authenticity, vulnerability, and the ability to critically reflect—whether as a comedian, whistle-blower, veteran, or aspiring leader—emerge as core virtues.

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