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The 17 Best Jokes About Donald Trump From His 2011 Comedy Central Roast

COMEDY CENTRAL Roast Of Donald Trump - Show
Donald Trump onstage at the Comedy Central Roast of Donald Trump in 2011. Photo: Jeff Kravitz/Getty Images

Back in 2011, smack in the middle of the first time he attempted to run for president, Donald Trump agreed to participate in a Comedy Central roast. It was a fitting move for a man who has been described as an “insult comic made by the Jim Henson studios,” but also for one who has proven to be extremely media savvy. The irony of roasts is that even though the target is being burned all night, he or she usually comes out of it looking good. That was certainly the case for Trump.

His roast felt like a purging of all the terrible thoughts people had about him at the time — namely, that he’s a narcissistic creep with bad hair and terrible business practices. Those things are all still very true, but the roast helped frame his unsavory traits as something that can be laughed off, opposed to factors that should — I don’t know — maybe disqualify him from being president.

While there were some jokes about his political ambitions — including arguably the best joke of the night (told by Snoop Dogg, no less) — they were all told incredulously. Watching it again now, with the Republican convention underway and Trump’s presence inescapable, it’s stunning to see, through the jokes that are told, how different the narrative was about him just five years ago. Part of that is due to the joke-vetting process — as is the case with every roast, Trump was able to say certain topics were off-limits. Even so, it’s strange to think about Trump in a context where he isn’t being discussed as a racist or a fascist; this was even before the whole birther mess.

At the time, Trump becoming president was a joke, not a daily fear for many people. Even Trump himself, when he said at the end of the roast that he “will easily go down as the greatest president in the history,” seemed like he was just kidding. Now that we know he wasn’t, it’s interesting to look back at the best jokes that were told about him that night, which I’ve organized by subject. Right now, any laugh we can get about the Trump situation feels worthwhile.

Trump famously has stupid hair and a weird red face that resembles a bull’s-eye. Jokes hit the target.

“Don’t laugh at a hair joke, Trump. Look at that helmet. What do you say to a barber to get that type of haircut … ‘I fucked your daughter?’” — Lisa Lampanelli

“Donald, you’re also responsible for that awful show The Apprentice. The worst part of that show is having to look at your face. Your face is so big and bloated with such a bad hairpiece, I’m surprised it’s not married to Kelly Preston pretending not to be gay.” — Whitney Cummings

Trump is gross, especially toward women, especially when that woman is his daughter. The roasters took note.

“Donald is very happy with his lovely wife, insert name here.” — Lampanelli

“You made Trump more than just a name. You made it a brand. A brand like Massengill. Because you’re a bloated, stinky douche.” — Lampanelli

“I wish that I had half of your money. But for that you need a 20-year-old’s pussy and a divorce lawyer.” — Snoop Dogg

“You got Melania a huge, 12-karat-diamond engagement ring. You should not have gotten her a diamond, now she knows what hard is supposed to feel like.” — Cummings

“The Donald and I have a lot in common: We both live in New York, we both play golf, we both fantasize about his daughter.” — Jeff Ross

Bad at Business
Trump likes to say he’s good at business, whereas evidence indicates that he’s actually bad at business and was just born rich.

“Tonight we honor a self-made millionaire. He started with nothing, worked hard, and made a fortune … That man is Fred Trump, Donald’s dad. That’s right, for all his self-starter bullshit, he’s basically Jaden Smith with a comb-over.” — Seth MacFarlane

“You put up more useless hotels than an autistic kid playing Monopoly.” — Lampanelli

“Donald Trump, without a doubt, you’re a New York landmark. Which means it’s only a matter of time before you bulldoze yourself to build some gaudy, tacky monstrosity and put your name on it.” — Larry King

“Donald, you have a great sense of humor. You’ve been happy to embarrass yourself on Saturday Night Live and in the casino business.” — Anthony Jeselnik

“And Donald, I’m not even sure if you’re aware of this, but the only difference between you and Michael Douglas from the movie Wall Street is that no one’s going to be sad when you get cancer.” — Jeselnik

Trump likes Trump so much, he thought he could run for president even though everyone was like, You can’t, Trump. He showed them. But during the roast, they showed Trump that his self-regard is unpleasant.

“This guy has an ego. When Trump bangs a supermodel, he closes his eyes and imagines he’s jerking off.” — MacFarlane

“Melania, you look so beautiful tonight. Give her a round of applause. You’ve been such a good sport. So gorgeous. These two are so compatible, because they both yell out Donald’s name when they climax.” — Ross

Political Aspirations
Trump is going to be the Republican nominee for president. In 2011, this seemed like a stupid idea. It seems like a stupid idea in 2016 as well, yet here we are.

“As long as I have you here, it’s pronounced ‘huge,’ not ‘uge.’ And here’s another one, it’s pronounced ‘I am fucking delusional,’ not ‘I am running for president.’” — MacFarlane

“Donald says he wants to run for president and move on into the White House. Why not? It wouldn’t be the first time you pushed a black family out of their home.” — Dogg

“And now you’re going to run for president. Don’t you think that’s a really cool idea, you guys? You’ll keep them honest. You’ll keep them honest, Donald. Personally I hope you win because I can’t wait for the assassi… I mean inauguration.” — Ross

17 Best Jokes from Trump’s Comedy Central Roast