So to Speak: The Free Speech Podcast

Ep. 260: Remembering 'Free-thinking' Writer Nat Hentoff

Date: December 19, 2025
Host: Nico Perino (FIRE)
Guests: David Lewis (Director, The Pleasures of Being Out of Step), Nick Hentoff (Nat’s son)

Episode Overview

This episode commemorates the 100th birthday of Nat Hentoff—a legendary journalist, civil libertarian, and jazz critic. Host Nico Perino is joined by Nat’s son, Nick Hentoff, and filmmaker David Lewis, whose documentary The Pleasures of Being Out of Step profiles Nat’s life. Together, they explore Hentoff's six-decade career, his unapologetic defense of free speech, his iconic status in music journalism, and the unique blend of activism, controversy, and integrity that defined his legacy.

Key Discussion Points

1. Who Was Nat Hentoff?

• Long career in journalism (over 60 years): Known for his work on civil liberties, jazz criticism, and political commentary.
• Pioneering jazz critic: First non-musician to be named an NEA "Jazz Master," prolific writer of album liner notes.
• Books and journalism: Dozens of books on free speech, civil liberties, and music; best known for Free Speech for Me – But Not for Thee (1992).
• Interviewer of iconic figures: Malcolm X, Che Guevara, Bob Dylan, and many more.

2. Nat’s Free Speech Philosophy

• Defining principle: Free speech as a core part of individuality and democracy; refusal to self-censor, even when unpopular.
  • "Free speech was a defining characteristic of the individual. It imbued all aspects of life." (Nico Perino, 03:16)
• Civil libertarian: A "line drawer, not a balancer," meaning: principled and absolutist, not willing to compromise core ideals (50:04).
• Unbothered by controversy: Known for walking "into a garden party and put on a skunk suit" (07:28), willing to challenge orthodoxies on left and right.

3. Legacy in Jazz and Journalism

• Liner notes and jazz community: Educated generations about jazz by contextualizing records with in-depth, musician-focused essays.
  • "A lot of people learned about jazz by reading those liner notes." (David Lewis, 05:07)
• Ethical approach: Respected musicians as artists, not just entertainers; formed strong friendships despite occasional critical reviews.
• Bridge between music and politics: Saw jazz as a metaphor for the American ethos—individual voices harmonizing in a collective.
  • "We are individual voices…And we come together and that voice is different and sometimes larger than the sum of the parts." (Max Roach to Nat Hentoff, quoted by Matt Henshoff, 02:57)

4. Formative Years and Influences

• Immigrant family, anti-semitism, and integrity: Grew up in Roxbury, Boston—deeply shaped by Jewish identity, the immigrant struggle, anti-semitism, and activism.
• Francis Sweeney’s mentorship: Early experience with activist-mentor Sweeney taught him to stand alone with unpopular truths.
  • "She was the prototypical skunk at the garden party." (Nick Hentoff, 09:58)
• Family trauma: Father escaped a Belarusian community destroyed in the Holocaust; the personal became political.

5. Embracing Unpopular Views

• Pro-life advocate: Despite leftist associations, Nat became a pro-life proponent, opposing both abortion and the death penalty—an embodiment of "the seamless garment," believing in sanctity of life "from conception to death." (Nick Hentoff, 09:02)
• Critic of both political sides: Willing to speak out against the left and right, e.g. critical of President Obama’s drone strikes as well as the Bush administration.
  • "He did a famous cover for the Village Voice, George W. Obama." (David Lewis, 26:45)
• Subject of controversy: Ostracized at times, but respected for principle.

6. Encounters with Censorship, Activism

• Under scrutiny for activism: Early teaching at a leftist school brought unwanted government attention during McCarthy era (36:54).
• FBI surveillance: Interviewed by FBI for civil rights and antiwar activity, which he responded to by speaking publicly about official harassment.
  • “[FBI visit]...instead of being cowed...he did the exact opposite. He started on a tour of campuses, not only talking about his interview...but talking about everything they didn’t want him to talk to.” (Nick Hentoff, 37:36)
• Defender of the marginalized: Early opponent of Vietnam War, exposer of civil liberties abuses, champion of libraries and alternative journalism.

7. Journalistic Style and Personality

• Straightforward prose: Avoided florid style; aimed for clarity and substance.
  • "He wasn't a stylist...His voice was very straightforward and plain spoken." (David Lewis, 25:35)
• Relished debate and dissent: Saw "pleasures" in being out of step with consensus.
  • "There is a certain joy for him in being out of step." (David Lewis, 52:12)
• Motivated by ‘rage’ at injustice and cruelty: Anger—not politics—was his primary motivator.
  • "Somebody once asked him what was the principal motivation...and he had a one word answer, and that was rage." (Nick Hentoff, 42:22)

8. Impact and Enduring Legacy

• Shaped modern alternative journalism: Proto-blogger, influential in the evolution from mimeographs to Substack.
• Modeled civil libertarian courage: His approach endures as a challenge to today’s would-be dissenters.
• Living out free speech values: As Floyd Abrams said, "Nat didn’t just talk about free speech or write about free speech. He used it." (David Lewis, 35:14)
• Memorable maxims:
  • "His response to speech that he didn't like was always more speech." (David Lewis, 55:24)
  • "To get paid for your opinions, the more controversial the better, must be the best of all possible jobs." (Nat Hentoff, quoted by Nico Perino, 51:42)

Notable Quotes & Memorable Moments

• On principled dissent:
  • “He was the quintessential free speech civil libertarian, always principled and always fiery.” (Nico Perino, 03:16)
• On family recognition:
  • “The most frequent question I got…are you related to Nat Hentoff?…That’s been a feature of my life from the very beginning.” (Nick Hentoff, 05:36)
• On intersection of jazz and democracy:
  • “What do you think we do in jazz?…We are individual voices…larger than the sum of the parts.” (Max Roach to Nat Hentoff, 02:57)
• On being out of step:
  • “She was the one who taught me the pleasures of being out of step. And that’s where I got the title for the film.” (David Lewis, 52:12)
• On being a "skunk at the garden party":
  • “Going in and being willing to speak truth to power, even when that’s going to be unpopular and put you at odds with the people in the room.” (Nick Hentoff, 09:58)
• On not self-censoring:
  • "He couldn’t get him to admit that there was any form of free speech that didn’t...if it didn’t involve violence against other people, then everybody had a right to say it." (Nick Hentoff, 50:44)

Timestamps & Notable Segments

• Nat Hentoff: Journalism and “skunk at the garden party” legacy — (07:28)
• Nat’s pro-life stance and seamless garment philosophy — (09:01–09:12)
• On experience with Frances Sweeney and early influences — (09:58–12:06)
• Connection of jazz, democracy, and free speech — (02:57, 21:07, 25:35, 31:35)
• Facing government scrutiny, McCarthyism, and civil rights era activism — (36:54–39:24)
• Career-defining conflicts: Village Voice tenure, Downbeat firing, and jazz community relations — (27:53, 28:30)
• Free speech absolutism: line-drawer, not a balancer — (50:04)
• Hentoff’s legacy, impact on journalism, and advice on dissent — (52:12–55:24)

How to Learn More

• Watch the documentary: The Pleasures of Being Out of Step (available on OVID.tv)
• Read Hentoff’s books:
  • Free Speech for Me—But Not for Thee (1992)
  • Speaking Freely, Boston Boy, and his jazz criticism collections

Conclusion

Nat Hentoff embodied the spirit of dissent, principled free speech, and intellectual independence. Whether writing about jazz or politics, he refused to self-censor, relished the challenges of standing alone when necessary, and believed in the transformative power of both music and democracy. His life stands as a reminder of the importance of principled dissent in free societies.

“If you see something that's wrong, you've got to stand up and you've got to talk about it for as long as you can, as loudly as you can and as eloquently as you can.”
– Nick Hentoff (55:05)