Media

Here’s how you might end up in Don Lemon’s show in Boston Friday night

Ahead of his show at the Shubert with D.L. Hughley, journalist Don Lemon talks jokes, flying solo, Boston, and “Heated Rivalry.”

Don Lemon during the New Orleans Book Festival at Tulane University in New Orleans last month. Amy Harris/Invision/AP

I happen to reach Don Lemon on the day he’s getting a dishwasher installed at his New York home, so the dogs are upstairs with him.

“Hi, doggy! Hi, hi!” he says, as one settles at his feet — away, presumably, from kitchen chaos.

The honorary Emerson degree-holder, ’14, says his husband, Boston College alum ’06, realtor Tim Malone, is downstairs.  “He loves Boston.”

The independent journalist/host of The Don Lemon Show, will soon leave the pups for a trip to Boston, to take stage with comedian D.L. Hughley. Catch him tonight (Friday, April 17) at 7 p.m. at the Shubert Theatre for “DL + DL: Anything Goes.

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If the two DLs seem like an unlikely duo for a live stage performance, they have more in common than you might think: 

One, a longtime actor/comedian known for saying what he thinks when it comes to politics.  The other, a famously candid award-winning journalist who can be lowkey hilarious. 

Example: when I ask him what to expect at “Anything Goes.”

“I think we’re going to change the name because people don’t know what ‘anything goes’ actually means.”

My first introduction (and likely yours) to Lemon’s lighter side were the early CNN Live New Year’s Eve specials with Anderson Cooper and Andy Cohen. 

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In 2023, Lemon and CNN “parted ways” (per their statement) after 17 years. (“Water under the bridge,” he says now.)

These days, you can watch his New Year’s Eve antics, man-on-the-street interviews, insights, and hot takes on The Don Lemon Show — live daily on YouTube and podcast — and his socials

We talked news, journalism, “Heated Rivalry,” his rekindled friendship with one of the original Kings of Comedy, and more.


Boston.com: So tell me a little bit about what you’re bringing here to Boston.

Don Lemon: Something that Boston has never seen before. 

[laughs] OK.

You never know what you’re going to get with us. We’re bringing a variety of information, comedy and news. We’ve found that a trained career newsperson and a comedian-who-is-also-a-thought-leader is a great combination. So we’re bringing laughter, maybe some tears, maybe some joy, maybe a little angst about where we are as a country.

So he does his thing, you do your thing, then you come on stage together. 

I do my thing — I tell the audience: “This is where we are.” We’re going to give you some hope — but I’ve got to tell you the truth. Then D.L. comes on and makes everybody laugh. 

Then he brings me on. We’ll talk for a bit. We’re in conversation — we’re having some cocktails. We might have a special guest talk, then we’ll open it to Q&A.

What are some topics you’ve been discussing?

It’s fresh, so we don’t really have topics. We talk about what’s going on that day. We’ll see what transpires between now and Friday. Think about what was happening last Friday.

A world ago.

Completely different. So whatever is happening on Friday, we’ll talk about. One never knows. I like the energy of: “What are we going to discuss?” 

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Also he’ll joke about me, I’ll joke about him. I’ve learned how to tell jokes from him. I feed off of his energy. It’s heavy on politics, because that’s what’s in the zeitgeist.  

So how do you know D.L.? It might seem like an unlikely pairing — but you guys have been friends for a while.

Well, we were friendly. Then we fell out of favor with each other. He didn’t like how I handled corporate media — he thought I was too buttoned-up and middle-of-the-road. Some of it, he was right. So he’d talk sh— about me on the radio or whatever. I didn’t care. 

[laughs] OK.

I get criticism, that’s part of being in the public eye. But then my mom is a huge fan of his. She goes, “I really like D.L., you guys should talk. I think you’d be great [as a team] blah, blah, blah.”

And Jasmine [Sanders], his co-host [on his radio show, the The D.L. Hughley Show] was saying the same thing to him: “I really like Don, you guys should talk.” Somehow Jasmine and my mother got together — I don’t know if it was Facebook or what — and they put us together.

And something clicked.

It clicked. Then I went to a City Winery show about a year ago, and [was approached], “Oh, we’ve been wanting to get you here.” And I said, “Ah! I have a great idea. Hang on.” I called D.L. and before I could get it out, he’s like: “Yes.”

@donlemon I’m cutting up with @DL ♬ original sound – Don Lemon

And did you two know immediately what this show would be? Do you plan it out? Is there a script?

Initially, what I did at the beginning [of the show] was give you an idea of where the world is, and some of that would be scripted. 

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So after my arrest in Minnesota, it just became unscripted. I just sat there — it was terrifying — without a script, and I said, “Well, I’m just going to talk to you because, I don’t like this, but I am the news; I’m in the news. So let’s just talk.”

Don Lemon, the former CNN anchor, reporting from the scene of demonstrations in Broadview, Ill., on Oct. 12, 2025. – Jamie Kelter Davis/The New York Times

And I don’t even know how to explain it. It was an out-of-body experience. It was fantastic to be able to sit there and just talk about my life, because I’m usually scripted.  

It was invigorating; I felt like I made an evolution into a different level of performance. So you never know. We’re free with what we do. 

And obviously, D.L. is not scripted — he’s doing jokes.

When did you reconnect with D.L.?

A few years ago. We’d talk on the phone and have these long conversations at night about life.  

When I left CNN, he said the way that I conducted my exit and myself since, he was really impressed.

What’s that transition to independent journalism been like?

Terrifying and thrilling at the same time. Everyone says, “Oh it happened so quickly.” It wasn’t overnight. I worked my ass off. I just sit and do content every day. 

So it gives me a new degree of autonomy and self-confidence. I think many in the news business, working in corporate media, may not have that same confidence that — if they go away from whatever three big letters they work for — that they’ll still be relevant, or have a career, or be able to prosper. 

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I’ve proven to myself, and perhaps others, that it’s possible. It’s not necessarily the three letters that precede your name, like CNN’s Don Lemon. It’s just Don Lemon.

That must feel empowering.

It does! But listen, it’s more than just journalism. You’ve got to have a certain degree of fearlessness, along with ambition, confidence, and credibility. The biggest qualification to survive in this new digital-media landscape we’re in: authenticity.

People want [to hear from] people they like, they trust, they know. They don’t want it filtered through gatekeepers. 

The standard [line] is: “No one has ever told me what to say or what to do.” And it’s like, no, they don’t have to. But if you see people around you get ejected, who are a little bit more authentic, a little bit more candid, you self-adjust unconsciously. 

Before I said something, I’d weigh it 2, 3, 4, 5 times. Should I say this? You might upset this person, or this group, or this advertiser. I don’t have to worry about that anymore. And it’s amazing.

Do you find with this show, given everything going on, people almost need to have that laugh with the news?

They do, even if it’s to vent frustration. Laughter helps. Truth-telling helps. And a couple of drinks … It’s a little sugar that makes the pill go down. 

People also need to be in communion or in community with each other. When you’re sitting in a room full of mostly like-minded people, and you’re getting things off your chest and learning new things — it’s quite an experience. It’s almost like going to church, except secular.

Is it a release for you, too? 

Of course. Sometimes watching the news is just too much. It’s too depressing; it’s overwhelming; it’s inundating. This is a way to be informed without being inundated.

So what are you like as a regular guy when you’re not reporting the news? What do you watch? What are you reading?

I’m reading Iyanla Vanzant’s new book, “Spiritual Hygiene.” It teaches you how to detox or declutter your spirit or your soul. Also on the nightstand: a James Baldwin collection. I’m a big James Baldwin fan. I’ve read every single book, and now I’m just rereading.

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And what I watch? Boston’s a big hockey town. I just watched “Heated Rivalry.”

[laughs] Nice. We do love our Bruins.

Oh! I met one of your hockey players on the street, Nikita [Zadorov], the big Russian guy [6-7, 255 pounds]. I was doing man-on-the-street interviews. I was talking to him, and noticed: “This is a big dude.”

He’s huge. 

I said, “Are you a hockey player?” He goes, “Yes. How did you know?” And I was like, “Your legs.”

We talked some politics, not much. He’s a really nice guy. But I just randomly ran into him in my neighborhood.

That’s amazing. Will you do any man-on-the-street interviews in Boston?

Yeah, if the news warrants it, I’ll do them in Boston. It’ll be interesting doing man-on-the-street interviews with Bostonians because they’re very opinionated, and I love the accent. 

You’ve got to do one. New Englanders give the best man-on-the-street content. Anything to add about the Boston show?

You have to come with an open mind. You may not agree with everything. But that’s life.

Interview has been edited and condensed. 

Lauren Daley is a freelance culture writer. She can be reached at [email protected]. She tweets @laurendaley1, and Instagrams at @laurendaley1. Read more stories on Facebook here.

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Lauren Daley is a longtime culture journalist. As a regular contributor to Boston.com, she interviews A-list musicians, actors, authors and other major artists.

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