Worst Boyfriend Ever — one of Substack's most controversial and compelling writers — did a live reading in NYC, and I was there. I took the 2 train down to 14th Street on a Saturday night, something I haven't done solo in maybe a decade, and walked into a packed bar that was definitely not built for 120 people. WBE read offensive material while people walked out mid-reading in protest. He threw books at audience members. He didn't flinch once. What I left with wasn't just a recap of a wild night — it was clarity about the crowd I want to be around and what fearlessness actually looks like in practice.

Timestamps:

• 1:40 – Intro and call for ratings/reviews
• 3:06 – How I discovered Worst Boyfriend Ever on Substack
• 4:28 – Arriving at the bar, navigating to the reading space
• 8:27 – WBE takes the stage and reads chapter one
• 10:20 – People start walking out mid-reading; WBE starts throwing books
• 13:14 – Danny Lee reads (the best reader of the night)
• 13:57 – The Indian girl reads from her phone
• 16:19 – The Amsterdam dude reads and works the crowd
• 17:49 – The Louis CK lookalike laughs at his own jokes
• 19:43 – WBE returns: "Why I Like Asian Girls" and "Why You Shouldn't Love Women"
• 20:52 – Closing thoughts on finding your crowd and overcoming fear

Links:

• Worst Boyfriend Ever on Substack: jamesguilty.substack.com

Contact: [email protected]

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Episode #184

Only about a third of colonists supported the American Revolution—another third stayed loyal to Britain, and the rest remained neutral. If a motivated minority could overthrow an empire and reshape history, what does that mean for today? This episode challenges the assumption that because most Americans aren't extremists, we're safe from extremism taking hold. Majority comfort might be the wrong measure of democratic safety.

To all of you who are engaging in illegal activity, asking someone "are you a cop" is not how you avoid getting arrested.

Have you ever been arrested after a cop told you he wasn't a cop? [email protected]

A second fatal ICE shooting in Minneapolis has intensified anti-ICE protests and put immigration enforcement back at the center of a public backlash. In this episode, I argue that the right is losing the fight not because of policy, but because of messaging — and that shock-and-awe enforcement without public trust is a losing strategy in a democracy. I break down why PR matters in political conflict, how past deportation strategies avoided this moment, and what a more effective approach to immigration enforcement could actually look like.

Do you want to contact the show? Send me an e-mail at [email protected]

The civil rights movement aimed for a society where race mattered less — not more — and where shared citizenship could outweigh skin color. Today's racial justice movement often pursues a very different goal: a multi-ethnic, multi-cultural society shaped around group identity. In this episode, I compare these two visions of equality, question whether either is fully achievable, and argue that even an imperfect post-racial ideal may offer more unity than a society built around permanent difference.

Want to get in contact with the host? Send an e-mail to E-mail: [email protected]

Anti-AI sentiment is growing, but the direction of the technology isn't up for a vote. In this episode, I argue that the push to slow or stop AI misunderstands how technological change actually works — and why resistance often comes from fear rather than strategy. This is a conversation about inevitability, adaptation, and what happens when people mistake moral discomfort for control.

E-mail: [email protected]

In this episode, I examine the fatal ICE shooting through the lens of protest culture and federal power. As activists increasingly attempt to obstruct immigration enforcement, I argue that moral certainty — especially among those insulated from the consequences — can turn dangerous. This isn't a defense of policy or personality, but a critique of how ideology, privilege, and symbolism collide with the reality of federal authority.

Want to contact me? Send me an e-mail at [email protected]

International law is treated like a global rulebook — but what happens when the most powerful country on Earth decides it doesn't apply?

In this episode, I'm sitting in the dark with the mic in my hand, giving you the hard dose most won't. Using recent U.S. actions in Venezuela as a case study, I break down why "international law" only exists when power allows it — and vanishes when it doesn't.

This isn't partisan rage or a straight news recap. It's a raw philosophical take on power, empire, and the dangerous logic of "might makes right." As a proud Black American patriot with no other country to fall back on, I wrestle with why loving America doesn't mean cheering every intervention — and why this precedent should worry every U.S. citizen.

In this episode, we dive into:

• Why no one can actually enforce international law on superpowers

• How oil, resources, and narratives drive foreign policy

• Patriotism vs. blind loyalty to government actions

• Whether the president even has authority to drag the country into these moves

• Nationalism, global humanity, and where to draw the line

📍 Timestamps

02:20 – Venezuela and the illusion of global rules 05:01 – I don't need to know about venezuela 08:38 – Trump doesn't have the authority to declare war 12:18 – "Might makes right," oil, and empire 18:38 – America does not need to dominate the globe

Share your thoughts: [email protected] (no "e" in philosophr)

🎧 If this episode made you think, consider subscribing, rating the show, or telling two friends — that's how audio like this spreads.

Topics and timestamps

• Diana Ross' New Year Eve performance (1:47)
• Audio only podcasts (3:11)
• That "get in shape" resolution is a trap (9:43)
• Lily Phillips just got Baptized (21:00)
• I'm conflicted when it comes to Mamdani (26:37)
• The "worst boyfriend ever" is an internet treasure (35:38)

Enjoy the podcast? Please remember to subscribe, rate, and review the podcast on iTunes. It really helps the show reach new listeners.

Want to get in contact with the show? Email us at [email protected]

Follow the host

Cruel on X: https://twitter.com/CruelPhilosophr

Cruel on Instagram: https://www.instagram.com/cruelphilosophr/

In this episode, I open up about what it feels like to create in a world where algorithms decide what gets seen, heard, or buried. From censoring words to forcing myself into niches I don't care about, I talk about the quiet ways creators lose their voice in order to survive online—and why I'm pushing back.

Follow me on X and Instagram @cruelphilosophr

Have feedback or want to contact me? Send an e-mail to [email protected]