The relationship between CBS’s Stephen Colbert and CNN is getting especially gushy as Monday marked the one-month mark until The Late Show is canceled. On Friday, Colbert presented Anderson Cooper with a silver medal for being his second most popular guest, and on Monday, The Lead anchor Jake Tapper returned the favor with a First Amendment pocket square that he said he will use on Saturday to troll President Trump with at the White House Correspondents’ Dinner and a painting of Colbert as Gollum from The Lord of the Rings.
Colbert began, “Nice to see you again. You know I enjoy your work, but what I forget when I haven't seen you in a while is how damn handsome you are… and dapper. I like the pocket square.”
On The Late Show With Stephen Colbert @JakeTapper pulls out a “freedom of the press” pocket square, says he’ll be wearing it to Saturday’s White House Correspondents’ Dinner because (as he points at it stuffed in his jacket pocket so its content is hidden) “there may be some… pic.twitter.com/IbJEczDf3k
— Brent Baker 🇺🇲🇺🇦 🇮🇱 (@BrentHBaker) April 21, 2026
Tapper then pulled out the pocket square and showed it for everyone to see, “This is a special freedom of the press and freedom of speech pocket square… Saturday night’s the White House Correspondents' Dinner, and there are a bunch of us that are going to be wearing these. These are from the Reporters Committee for the Free Press because there may be some guests there that are unfamiliar.”
Colbert knew who Trapper was alluding to, “Oh, this is the first time the president is going to be attending, right?”
Tapper agreed and then presented Colbert with a pocket square of his own and a fan for his wife Evie, “Now that you say so, yes. By the way, I brought you one… and this is for Evie.”
Colbert then recalled how his first WHCD was with Tapper, which Tapper also remembered "was a lot of fun, and then you came the next year and dropped a nuclear bomb on the press.”
“By nuclear bomb,” Tapper meant that Colbert criticized the media for not being anti-Bush enough, which sounds similar to the people who today claim the media is somehow not anti-Trump enough.
Jake Tapper came bearing gifts for Stephen Colbert including a good bye gift that was a painting he did of Colbert as Gollum, which is kind of weird when you think about (1/2) pic.twitter.com/zdYgp4G1KA
— Alex Christy (@alexchristy17) April 21, 2026
Tapper, however, was not done bearing gifts. In the second segment, Tapper unveiled a going-away gift for Colbert, “I wanted to do something special. I thought I could buy him a book, or I can buy him this. Last time, when you turned 60, I bought you some sort of hobbit, some old hobbit.”
After some riffing about how Colbert’s wealth makes him hard to shop for, Tapper continued, “So, I thought okay, you know, I was a minor in art in college. I dabble. So, I thought maybe I could paint something for you, and then somebody on my staff said, ‘Why don't you paint a picture of him, because he loves The Lord of the Rings so much, as a hobbit or a wizard.’ Hold on, hold on, hold on and then I said, ‘That's a great idea but you know what? He's been on the air for 11 years now. Let me check with Evie, his wife.' And she's like ‘Yeah, he's got plenty of those.’ He doesn't need another Stephen Colbert as a hobbit. He doesn't need another Stephen Colbert as a wizard. But I know you love The Lord of the Rings, and so I painted you this.”
Tapper then unveiled a giant painting of Colbert as Gollum, which is strange when you consider who Gollum is and what he represents: a cautionary tale of sin and corruption.
Here is a transcript for the April 20-taped show:
CBS The Late Show with Stephen Colbert
4/21/2026
12:19 AM ET
STEPHEN COLBERT: Nice to see you again. You know I enjoy your work, but what I forget when I haven't seen you in a while is how damn handsome you are.
JAKE TAPPER: Oh, you’re so kind.
COLBERT: Thank you. And dapper. And dapper. I like the pocket square.
TAPPER: Oh, yes. This is a special freedom of the press and freedom of speech pocket square.
COLBERT: What's it say? Show them. That's very nice.
TAPPER: Yeah, and we’re—I’m going to be—Saturday night’s the White House Correspondents' Dinner.
COLBERT: I did not know.
TAPPER: And there are a bunch of us that are going to be wearing these. These are from the Reporters Committee for the Free Press.
COLBERT: Oh, okay.
TAPPER: Because they’re may be some guests there that are unfamiliar.
COLBERT: Oh, this is the first time the president is going to be attending, right?
TAPPER: Now that you say so, yes. By the way, I brought you one.
COLBERT: That's so lovely.
TAPPER: And this is for Evie.
COLBERT: Oh, that's very nice. My southern belle.
TAPPER: I was getting fresh.
COLBERT: First correspondents' dinner I ever went to was with you.
TAPPER: You were my date.
COLBERT: Yeah, it was a lot of fun.
TAPPER: It was a lot of fun, and then you came the next year and dropped a nuclear bomb on the press.
COLBERT: Neutron. Neutron bomb. Everyone in the building was fine
…
TAPPER: I wanted to do something special. I thought I could buy him a book, or I can buy him this. Last time, when you turned 60, I bought you some sort of hobbit, some old hobbit.
COLBERT: Yes.
TAPPER: You're tough to shop for.
COLBERT: Thank you.
TAPPER: Let's be honest. You have a little money. So—
COLBERT: I'm comfortable.
TAPPER: You're comfortable. So, I thought okay, you know, I was a minor in art in college. I dabble. So, I thought maybe I could paint something for you, and then somebody on my staff said, “why don't you paint a picture of him, because he loves The Lord of the Rings so much, as a hobbit or a wizard.” Hold on, hold on, hold on and then I said, “That's a great idea but you know what? He's been on the air for 11 years now. Let me check with Evie, his wife.”
And she's like, “Yeah, he's got plenty of those.” He doesn't need another Stephen Colbert as a hobbit. He doesn't need another Stephen Colbert as a wizard. But I know you love The Lord of the Rings and so I painted you this.
COLBERT: It’s beautiful. It’s beautiful.
