Old School with Shilo Brooks artwork

Books · The Free Press

Old School with Shilo Brooks

by The Free Press

Fewer of us than ever are reading books for pleasure. Shilo Brooks is on a mission to change that. Old School is a new podcast from The Free Press about great books and how reading them can make us stronger, better men. The show features intimate conversations with fascinating men—from fitness gurus to philosophers—about the books that shaped their lives. New episodes out every Thursday.  Read with us: https://bookshop.org/lists/old-school-with-shilo-brooks

Chart trend

Position in the Books chart (US), last 90 days.

#1
all-time peak
29
days in the top 3 since Oct 2025

Latest episodes

Showing 20 · updated from the feed

A Note From Shilo

A message from our host. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jun 25
2 min

What ‘The Future Is Female’ Has Meant for Men

For decades, the fight for gender equality has squarely focused on lifting women up—in the workplace, politics, and beyond. But according to Richard Reeves, president of

Jun 18
57 min

Walter Isaacson on the Sentence That Created America

If America has a mission statement, it is this:   “We hold these truths to be self-evident, that all men are created equal, that they are endowed by their Creator with c

Jun 11
52 min

The WWII Novel That Explains America

In this special episode, Shilo Brooks is joined by Pulitzer Prize–winning historian Jon Meacham at the Jack Miller Center’s annual summit on civic education.  They took

Jun 4
55 min

Agatha Christie and the Kidnapping That Inspired Her Greatest Mystery

In this episode, Shilo sits down with veteran journalist Joe Nocera for a deep dive into the world’s best-selling novelist, Agatha Christie.  Nocera’s new investigative

May 28
54 min

Inside the Supreme Court with Amy Coney Barrett

In this special episode, taped live at the George W. Bush Presidential Center, Shilo sits down with Supreme Court Justice Amy Coney Barrett for a wide-ranging interview o

May 21
51 min

A New Series From The Free Press | The Lindbergh Conspiracies

Hi Old School listeners! Veteran reporter Joe Nocera has launched a six part series about the Lindbergh kidnapping. Enjoy episode one here and then head on over to ⁠The L

May 19
43 min

Roald Dahl: Genius and Bigot

For tickets to our live recording with Jon Meacham in Philadelphia, click here and register. Use code TFP for a 20 percent discount.  Roald Dahl gave the world Matilda,

May 7
49 min

How Sports Became Our Civic Religion

For tickets to our live recording with Jon Meacham in Philadelphia, click here and register. Use code TFP for a 20 percent discount.  In this episode, Shilo sits down wi

Apr 30
51 min

The Ancient Jewish Wisdom Behind a $5 Billion Company

For tickets to our live recording with Jon Meacham in Philadelphia, CLICK HERE and register. Use code TFP for a 20 percent discount.  As he built Kind Snacks into a $5 b

Apr 16
52 min

Neal Stephenson on AI, Rome, and How Civilizations Decline

Neal Stephenson, the prophetic author of cyberpunk classics like Snow Crash and The Diamond Age, has shaped how we imagine the future, from the metaverse to crypto to AI.

Apr 9
49 min

The Two Types of People Who Never Find Happiness

For tickets to our live recording with Jon Meacham in Philadelphia, CLICK HERE and register. Use code TFP for a 20 percent discount.  Life is short. How do we live it we

Mar 26
53 min

Hunting Humans for Sport

For tickets to our live recording with Jon Meacham in Philadelphia, CLICK HERE and register. Use code TFP for a 20 percent discount.  Richard Connell’s 1924 short story

Mar 19
54 min

Joan Didion Knew What Hollywood Would Become

The perfect book to read around the Oscars this weekend? Joan Didion’s Play It as It Lays. In this episode, Shilo sits down with Peter Savodnik to discuss Didion’s 1970

Mar 12
55 min

The NYC Public Defender Who Sends Books to Prisoners

In this episode, Shilo Brooks sits down with New York City public defender Ben Schatz to discuss the novel True Grit–and the nature of justice in America.   Ben founded

Mar 5
55 min

‘The Brothers Karamazov’ Helped Inspire the Catholic App Hallow

Alex Jones was using apps like Headspace and Calm to quiet his mind, but he had fallen away from his Catholic faith. Then he read The Brothers Karamazov, and everything c

Feb 26
54 min

‘Lolita,’ Jeffrey Epstein, and the Real Meaning of a Challenging Classic

One particular novel is all over the Epstein files: Vladimir Nabokov’s Lolita. Reportedly, this was the one and only book Jeffrey Epstein kept at his bedside table. He ow

Feb 19
49 min

The Secret Lives of Ordinary People

Dylan Thomas is one of the 20th century’s legendary poets.  In this episode, English journalist David Aaronovitch joins Shilo to discuss Thomas’ 1954 play Under Milk Woo

Feb 12
54 min

David Mamet vs. the Snobs

Pulitzer Prize–winning playwright David Mamet spent his childhood cutting class and reading at the local library. His first pick was Sinclair Lewis’s Main Street, which h

Feb 5
1 h 03 min

Colin Quinn on Incels, Woke Activists, and Peaking at 14

In this episode, legendary comic Colin Quinn dives into a cult classic that still makes him cry with laughter: John Kennedy Toole’s A Confederacy of Dunces. The novel fo

Jan 29
52 min

Chart positions

Where Old School with Shilo Brooks ranks today in each Apple Podcasts chart (US, Sep 13, 2026).

#150 ▼ 12 Books US

What listeners say

A curated, balanced selection of Apple Podcasts reviews.

I got a lot of enjoyment from listening to these podcasts, they push the gears of my mind into motion. The host is a deft hand at managing the conversations and digging deeper on key points. His critical thought and calm presentation makes you savor the podcast and want to read the books... immediately. I'm also an alum from St. John's College, which he sometimes cites on the podcast- if these discussions are up your alley, I really recommend looking into the educational programs there. Thanks for putting this together, Mr Brooks!

dcalifone · Nov 2025

I’m a huge Steve Rinella fan. I watch meateater with my son daily. Glad to find this podcast and see that Steve is one of the guests. Love that people are talking about old books.

Markuswallus15 · Oct 2025

We strive to present a balanced view by showing a diverse range of reviews from Apple Podcasts.

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About Old School with Shilo Brooks on Reason.fm

Here you find the Apple Podcasts chart positions of Old School with Shilo Brooks, its latest episodes to listen to directly, and reviews from listeners. Rankings are updated daily for the United States.

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