Mr. Reagan Counts Down Donald Trump's Top 16 Greatest Hits and Funniest Presidential Moments in American History

[00:00] Donald Trump's top 10 greatest hits. And

[00:03] by 10, I of course mean 16.

[00:06] >> Mr. Reagan,

[00:07] >> Donald Trump is the funniest president

[00:09] in American history. That is a fact. And

[00:13] the other day, I was working on

[00:14] designing some merchandise for

[00:17] Christmas. I ultimately settled on

[00:19] designing some Santa Claus stuff, but

[00:20] Santa Claus in my designs is Donald

[00:23] Trump. But as I was trying to come up

[00:25] with some funny ideas for this new

[00:27] merch, it occurred to me that Donald

[00:29] Trump himself has said so many

[00:31] brilliantly hilarious things over the

[00:33] years that maybe for inspiration, I

[00:35] should compile a few of Trump's funniest

[00:37] moments. And then I thought, well, why

[00:39] don't I just turn that into a video

[00:41] because who doesn't want to watch that?

[00:43] So, without further ado, this is my

[00:45] early Christmas gift to you. Allow me to

[00:48] present Donald Trump's top 10 greatest

[00:50] hits. And by 10, of course, I mean 16.

[00:53] He used to call me on the cell phone.

[00:57] [music]

[01:00] Call me on the cell.

[01:04] Number 16, the Hillary fatality. October

[01:07] 2016. It's the second presidential

[01:10] debate. Hillary Clinton is feeling smug.

[01:13] She's just finished attacking Trump and

[01:14] she's got that smirk on her face like

[01:16] she's already won. Trump picks up the

[01:18] mic and delivers what might be the

[01:20] greatest debate line in American

[01:22] history. Half the room explodes. The

[01:24] other half, well, they're still in

[01:27] therapy.

[01:27] >> It's just awfully good that someone with

[01:30] the temperament of Donald Trump is not

[01:32] in charge of the law in our country.

[01:34] >> Yeah, because you'd be in jail.

[01:36] >> Secretary Clinton.

[01:39] [cheering]

[01:41] >> Number 15. Vance and Rubio need new

[01:44] shoes. So JD Vance told this story just

[01:47] the other day and it's moments like this

[01:49] where we all kind of think, man, I wish

[01:52] I was in the room for that.

[01:53] >> Today I'm in the Oval Office with the

[01:55] president of the United States and our

[01:57] great secretary of state Marco Rubio and

[01:59] we're talking about something really,

[02:01] really important and the president kind

[02:02] of holds up his hand and says, "No, no,

[02:04] hold on a second. There's something much

[02:06] more important." And he le he he peers

[02:08] over the Resolute desk and he says,

[02:09] "Marco, JD, you guys have shitty shoes.

[02:15] we got to get we got to get you better

[02:16] shoes. And he's actually asking our size

[02:19] in the middle of this conversation. He's

[02:21] asking for our size so that he can make

[02:23] sure that we get the right shoes. And he

[02:25] asked this other policy. He said, "I'm

[02:26] going to get you some shoes, too." And

[02:28] so he says, "Marco, what's your shoe

[02:29] size?" And Marco's apparently an 11 12.

[02:31] He says, "You know, JD, what's your shoe

[02:33] size?" My shoe size is 13. And he asked

[02:36] this politician, who I won't embarrass,

[02:38] what his shoe size is, and he says

[02:39] seven. [laughter]

[02:43] president. He kind of leans back in his

[02:46] chair and says, "You know, you can tell

[02:48] a lot about a man by shoes."

[02:52] >> Number 14, Trump's brutal honesty. This

[02:56] is from the Eugene Carol deposition.

[02:58] Now, most people would try to be nice to

[03:00] a lawyer that might be able to send them

[03:02] to prison for years. Not Trump. Trump

[03:05] just looked at this woman and said

[03:07] exactly what he was thinking. When you

[03:10] said in that video that Ms. Leadeds

[03:12] would not be your first choice, you were

[03:15] referring to her physical looks.

[03:18] Correct.

[03:18] >> Just the overall not I look at her, I

[03:21] see her. I hear what she says. Whatever.

[03:24] You wouldn't be a choice of mine either

[03:26] to be honest with you. I hope you're not

[03:27] insulted. I would not under any

[03:30] circumstances have any interest in you.

[03:33] I'm being I'm honest when I say it. Uh

[03:35] she I would not have any interest in.

[03:38] Number 13, self-deprecating humor, part

[03:41] one. October 2025, Donald Trump is in

[03:44] Japan addressing the troops at a naval

[03:46] base, and he hilariously lets out a

[03:48] little secret about Donald Trump

[03:50] psychology.

[03:51] >> As commander-in-chief, I never forget

[03:53] that our ultimate strength does not come

[03:55] from equipment. It comes from the men

[03:58] and women of the rank and file. That's

[04:01] true. It comes from you people.

[04:03] Incredible people. Goodlooking people.

[04:05] Too many good-looking people. I don't

[04:06] like good-looking people. I never liked

[04:09] good-looking people. I'll be honest with

[04:10] you. I've never admitted that before.

[04:13] >> Number 12, the Kim Jong-un photo op.

[04:16] June 2018, Singapore. Donald Trump meets

[04:19] with Kim Jong-un. This is one of the

[04:21] most critical moments of international

[04:22] diplomacy in American history. And while

[04:25] most presidents would have been nervous

[04:27] and would have chosen their words very

[04:28] carefully, that just ain't Donald Trump.

[04:31] The man just does things his own way.

[04:34] and he knows what's truly important

[04:36] about a photo op.

[04:37] >> Getting a good picture of everybody so

[04:39] we look nice and handsome and thin and

[04:42] >> beautiful.

[04:47] >> Number 11, the Elizabeth Warren apology.

[04:50] Montana rally 2018. Donald Trump had

[04:52] been calling Elizabeth Warren Pocahontas

[04:54] for quite a while by this time and he

[04:56] was starting to feel a little remorse.

[04:58] And so Donald Trump did a very

[05:00] untrumpian thing. He apologized.

[05:03] >> Pocahontas. They always want me to

[05:05] apologize for saying it.

[05:07] >> And I hereby Oh, no. I want to

[05:10] apologize. I'll use tonight. Pocahontas.

[05:13] I apologize to you. I apologize to you.

[05:16] I apologize

[05:18] to the to the fake Pocahontas. I won't

[05:20] apolog.

[05:24] April 2024. Joe Biden had just called

[05:26] MAGA supporters garbage. So what does

[05:29] Donald Trump do? He rolls up in a

[05:31] garbage truck.

[05:32] >> How do you like my garbage truck? This

[05:34] truck is in honor of Kamla and Joe

[05:37] Biden.

[05:38] >> This was an absolutely epic publicity

[05:40] stunt. But that wasn't even the best

[05:42] part. The best part was his retelling of

[05:45] events. No one tells stories quite like

[05:48] Donald Trump.

[05:49] >> I'm in this beautiful plane. I'm

[05:50] enjoying myself. I have a wonderful suit

[05:53] on. And one of my people came in and

[05:55] said, "Sir, you know the word garbage is

[05:58] the hottest thing right now

[06:01] out there. The hottest thing out there.

[06:03] Sir, would you like to drive a garbage

[06:06] truck?"

[06:11] Now, we're about, you know, 30 minutes

[06:12] from landing. We had to do this pretty

[06:14] quick. I said, "It's sort of cool,

[06:15] though, isn't it?" Cuz, you know, they

[06:17] brought this brand new, gorgeous truck,

[06:19] wonderful driver. He looked like uh

[06:21] Carrie Grant in his prime. you know who

[06:23] that is. And then I actually said, "How

[06:26] the hell do you get into this truck?

[06:27] It's way up high. It's a big one." And I

[06:30] said, "Man, this is bad." Cuz now I have

[06:32] all the cameras are all watched. Look,

[06:34] look at all the fake news. They were

[06:35] most of them.

[06:38] No, most of them, many of them were

[06:40] there. And I'm saying, "Oh boy." You

[06:42] know, one little mistake with these guys

[06:44] and your your political career is over.

[06:46] You can't even. So I said, "Man, if I

[06:48] don't get up there, this is going to be

[06:49] very embarrassing."

[06:52] these stupid people, they'll say he's

[06:54] cognitively and physically impaired.

[07:00] So look, so the stair, the first stair

[07:03] is like up here. I say, "Shit."

[07:08] So So I had the adrenaline going and I

[07:11] made it.

[07:16] [screaming]

[07:17] I made it. And then I gave a little news

[07:21] conference from the front of the, you

[07:22] know, they asked their wise guy

[07:23] questions and everything and then uh we

[07:27] drove about two feet. I got out, got

[07:29] into the plane

[07:32] and then and I come into the arena and I

[07:34] say, "Where's my jacket? I want to get

[07:36] out of this thing."

[07:39] And they said, "It would be unbelievable

[07:41] if you could wear it on stage." I said,

[07:48] >> [applause and cheering]

[07:49] >> And I said, "No way." They said, "Oh,

[07:52] okay, sir." I said, "Get me my jacket,

[07:54] but if you did, you know, it actually

[07:58] makes you look thinner." I said,

[08:03] and they got me. I said, "I want to wear

[08:05] it on stage."

[08:07] When they said I look thinner, I said,

[08:10] "In that case,

[08:12] I may never wear a blue jacket again.

[08:15] and I may go.

[08:18] >> Number nine, telling it like it is.

[08:20] Ordinary everyday patriotic Americans

[08:22] love Donald Trump for a variety of

[08:25] reasons. But Trump supporters are very

[08:27] pragmatic, downto-earth people. So

[08:29] perhaps the one thing that Americans

[08:31] love about Donald Trump more than

[08:32] anything else is that he says it like it

[08:35] is.

[08:36] >> You know what woke means? It means

[08:37] you're a loser. Everything woke.

[08:40] [cheering]

[08:42] Everything woke.

[08:45] It's true. Everything woke turns to

[08:49] Okay. It's true. It's [cheering]

[08:52] true. Look at what's happening.

[08:57] [cheering]

[08:58] Number eight, Tim Waltz. Back in 2024,

[09:01] Trump was campaigning against Camela

[09:03] Harris and Tim Waltz. Politics can be

[09:05] cutthroat, and Donald Trump was fighting

[09:08] hard to win. It was absolutely critical

[09:11] that Trump accurately assessed the

[09:13] threat that he faced in the upcoming

[09:15] election. And Donald Trump did exactly

[09:18] that.

[09:18] >> I used to think the Democrats were crazy

[09:21] for saying that men have periods.

[09:24] But then I met Tim Waltz.

[09:29] >> Number nine in memoriam. In classic

[09:32] Trump fashion, Donald Trump provided for

[09:34] us the greatest comedic eulogy in the

[09:36] history of mankind.

[09:38] >> The United States has conducted an

[09:40] operation that killed Osama bin Laden.

[09:43] >> Abu Bakar Albaghdadi is dead. [laughter]

[09:48] >> The United States launched a targeted

[09:50] operation against that compound.

[09:52] >> They did a lot of shooting and they did

[09:54] a lot of blasting. Even not going

[09:56] through the front door. You know, you

[09:58] think you go through the door. If you're

[10:00] a normal person, you say, "Knock, knock.

[10:03] May I come in?" [laughter]

[10:04] >> After a firefight, they killed Osama bin

[10:07] Laden and took custody of his body.

[10:10] >> He died like a dog.

[10:12] >> But his death does not mark the end of

[10:14] our effort.

[10:15] >> A beautiful dog, a talented [laughter]

[10:17] dog.

[10:18] >> We give thanks for the men who carried

[10:20] out this operation.

[10:21] >> And I don't get any credit for this, but

[10:23] that's okay. I never do. But here we

[10:26] are. Number six, self-deprecating humor,

[10:29] part two. Donald Trump is known for

[10:31] slaying his political enemies with epic

[10:33] roasts, but he's also the absolute king

[10:36] of the self-deprecating joke, as we've

[10:38] already seen. But this might be the best

[10:41] one of them all. Somehow, by saying

[10:43] absolutely nothing, Donald Trump managed

[10:45] to roast himself as the ultimate

[10:47] narcissist.

[10:48] >> Tradition holds that I'm supposed to

[10:50] tell a few self-deprecating jokes this

[10:54] evening. So, here it goes.

[10:57] Nope. I've got nothing.

[11:01] I've got nothing.

[11:03] There's nothing to say. Number five, it

[11:07] comes from China. When a politician

[11:09] expresses himself, it is uncommon and in

[11:11] fact, I would go so far as to say it has

[11:13] never happened in the history of

[11:14] politics that their particular

[11:16] pronunciation of a single word becomes a

[11:19] major world event.

[11:20] >> Why do you keep calling this the Chinese

[11:22] virus?

[11:23] >> It comes from China. That's why comes

[11:26] from China. I want to be accurate.

[11:27] >> Trump's pronunciation of the word China

[11:29] became such a global phenomenon that it

[11:31] was even turned into a trending song.

[11:34] Comes from [music] China.

[11:38] Number four, Haitian immigrants. Now, if

[11:41] you think that creating a global

[11:42] phenomenon by the pronunciation of a

[11:44] single word is impressive, consider that

[11:46] Trump did this twice. The second time it

[11:49] wasn't a word, but three short

[11:51] sentences. in Springfield. They're

[11:54] eating the dogs, the people that came

[11:56] in. They're eating the cats. They're

[11:58] eating They're eating the pets of the

[12:02] people that live there.

[12:03] >> And again, this major world event was

[12:06] turned into a trending song.

[12:08] >> They're eating the dogs. They're eating

[12:09] the cats. Eat the cat. Eat the cat.

[12:13] >> Number three, white dudes for Harris.

[12:15] Now, in this clip, Donald Trump actually

[12:16] repeats a joke that was popular at the

[12:18] time, and he didn't get it exactly

[12:20] right. But considering that he was

[12:22] targeting white dudes for Harris, it was

[12:24] an absolute bullseye.

[12:26] >> There's a group called White Dudes for

[12:28] Harris. Have you seen this? White Dudes

[12:30] for Harris. Anybody know? Are some of

[12:32] you here? White Dudes for Doesn't sound

[12:34] like it, but I'm not worried about them

[12:37] at all because their wives and their

[12:40] wives lovers are all voting for me.

[12:43] [cheering]

[12:44] >> Number two, Trump says it exactly how he

[12:47] sees it. November 29th, 2025, Mara Lago.

[12:51] Donald Trump wanted to recognize a small

[12:53] but significant constituency that was

[12:55] there that day. Gays for Trump. And

[12:58] let's just say the recognition didn't go

[13:00] quite according to plan. [laughter]

[13:03] That's a This is a good one.

[13:05] >> Thank you very

[13:13] [laughter]

[13:18] Number one, the moment Donald Trump

[13:20] became president. October 2015, the very

[13:23] first Republican debate. Megan Kelly is

[13:26] hitting Trump hard. How does Trump

[13:28] respond? He responds with the single

[13:30] most legendary line ever uttered in a

[13:32] presidential debate. It was the line

[13:34] that won Donald Trump the presidency. It

[13:36] was all over after this.

[13:38] >> You've called women you don't like fat

[13:40] pigs, dogs, slobs, and disgusting

[13:44] animals. your Twitter account.

[13:46] >> Only Rosie O'Donnell.

[13:50] >> No, it wasn't.

[13:55] >> All right, I hope you guys liked these

[13:57] gems. If I missed a good one, feel free

[13:58] to drop it in the comment section below.

[14:00] I'll be checking those out. As always,

[14:02] that's it for me. And remember, it's not

[14:04] that liberal friends are ignorant. It's

[14:05] just they know so much that is not so.

[14:07] Good night.

[14:08] >> We're at war with the most dangerous

[14:10] enemy that has ever faced mankind in his

[14:12] long [music] climb from the swamp to the

[14:13] stars. And it's been said if we lose

[14:15] that war and in so doing lose this way

[14:17] of freedom of [music] ours, history will

[14:19] record with the greatest astonishment

[14:20] that those who had the most to lose did

[14:22] the least to prevent its happening. If

[14:24] we lose freedom here, there's no place

[14:26] to escape to. This is the last stand on