The Freedom Reader artwork

The Freedom Reader

Conan O’Brien Needs A Friend

April 9, 2026

Conan talks to Reginald from New Haven Connecticut about a past mistake that led him to a life of enrichment, education, and eventually the founding of FreedomReads.org, a non-profit that transforms the experience of incarceration by opening libraries in cellblocks.
Speakers: Conan O'Brien, Reginald
**Conan O'Brien** (0:02)
Malcolm in the Middle is back. Bryan Cranston, Frankie Muniz, Jane Kaczmarek, and the rest of the family returned for a four-part revival event on Hulu and Hulu on Disney+. Turns out Malcolm's been hiding from his family for years, but Hal and Lois are determined to get him to their 40th wedding anniversary, and there is no escaping family. We all know that too well. Stream Malcolm in the Middle, Life's Still Unfair, starting April 10th on Hulu and Hulu on Disney+. Hulu on Disney Plus requires bundled subscription. Terms apply.
Ever invest in something that seemed incredible at first, but didn't live up to the hype? Yeah, all the time. Yeah, I did that with an all potato restaurant.

**Reginald** (0:42)
Oh no.

**Conan O'Brien** (0:46)
Marketers know that feeling. They optimize for the numbers that look great, like impressions, but then they don't see revenue. You don't know what I'm talking about, don't you, Sona? Oh yeah, all the time. Yeah, LinkedIn has a word for that, bullspend. Bullspend. Yeah, instead you can get the highest ROAS of major ad networks with LinkedIn ads. Cut the bullspend.
Advertise on LinkedIn. Spend $250 and get a $250 credit. Go to linkedin.com/conan. Terms apply.

**SPEAKER_4** (1:20)
Conan O'Brien Needs a Fan. Want to talk to Conan?

**Reginald** (1:23)
Visit teamcoco.com/callconan.

**SPEAKER_4** (1:27)
Okay, let's get started.

**Reginald** (1:29)
Hey, Reginald. Welcome to Conan O'Brien Needs a Fan. Hey, how's it going?

**Conan O'Brien** (1:33)
Hey, Reginald, how are you?

**Reginald** (1:34)
I'm delightful, man. I'm doing great, honestly.

**Conan O'Brien** (1:37)
Yeah. I have been reading your bio, your story, your Marvel origin story, Reginald, and it's fascinating. It's amazing.

**Reginald** (1:50)
Thank you. It doesn't rival yours. I mean, yours is amazing. Mine is just, I'm just trying to make it out here.

**SPEAKER_5** (1:57)
No, yours is better.

**Conan O'Brien** (1:58)
Yeah, I'm sorry, Reginald. Reginald, I love to, I love to toot my own horn, but no, you have me beat by a country mile. You just have an amazing story. You have a law degree from Yale Law School, and which is insanely impressive. And you have an MFA in poetry. And here's what's, those are incredibly impressive accomplishments. And then you add to it that when you were 16, you participated in a carjacking and went to prison for eight and a half years.

**Reginald** (2:37)
Yeah, that was not as impressive. I think that was the bane of my existence, but I think you live and learn. And for me, you know, picking up a gun was the most crazy, baller style, violent thing I've ever done in my life.

**Conan O'Brien** (2:50)
Yep.

**Reginald** (2:51)
And nobody tells you that you could do something at 16 that will change your life forever. You know, as many teachers that used to sell me, you know, I would end up in jail or I could end up in dead because I lived in a bad neighborhood, so to speak. Right. I didn't really understand that I could change my life forever. And I did, I changed my life forever. So that's the kind of devastating thing about it is recognizing that I changed my life forever.

**Conan O'Brien** (3:16)
Well, there's so much to, people like to say, unpack here. There's so much to talk about. You, as far as I know, you spent a lot of time in solitary when you were in prison. And while you're in solitary, you discovered books. Is that correct?

**Reginald** (3:40)
Yeah, I did. I did two years off and on in solitary, but the thing that's really remarkable is, I'm 18 years old, 17 years old, I'm in a hole, and they took all of your books from me. And the thing is, 24 hours in a cell with just four walls, not as beautifully decorated as the walls around me.

**SPEAKER_5** (3:57)
Yeah.

**Conan O'Brien** (3:59)
I'm going to say, that's some impressive artwork around you.

**Reginald** (4:04)
And I was unraveling, and I heard a guy call out for a book, and I realized that these dudes had created an underground library for themselves. And all you had to do is call out for a book, and they would send you one. And so I said, hey, yo, send me a book. And they sent me this anthology called The Black Poets. And that introduced me to Robert Hayden, Lucille Clifton, Sonia Sanchez, Langston Hughes, Sterling Brown, Ethridge Knight. And I'm reading these words, and I realized that these poets were able to capture an entire life in 14 lines.

**Conan O'Brien** (4:36)
Yeah.

**Reginald** (4:37)
And I remember buying two books. This is the first books I bought with my money. It was a Sonia Sanchez book called Under a Supremal Sky, and it was Sun Tzu's The Art of War.

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