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The 14 funniest lines from last night’s roast of Donald Trump at the DNC

The 14 funniest lines from last night’s roast of Donald Trump at the DNC

Michelle Obama JB Pritzker Barack Obama Stephanie Grisham Doug Emhoff DNC 2024 Donald Trump zingers
Andrew Harnik/Getty Images; Bill Clark/CQ-Roll Call, Inc via Getty Images; MANDEL NGAN/AFP via Getty Images

What innuendo was President Obama making when he mocked Trump with his obsession with crowd size, writes John Casey.

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Did you have fun last night? I sure did! How can you not be enthralled with former President Barack Obama and his incredible wife, former First Lady Michelle Obama? Yes, they have unmatched oratory skills, and an ability to rouse the crowd with show-stopping lines, but they also make an exceptional comedy team.

Not since the likes of George Burns and Gracie Allen has America seen a husband and wife who can deliver punchlines with aplomb. Admittedly, only those of us who are of a certain age will appreciate this metaphor. As someone who dabbled in stand-up comedy, it is clear that their pauses, mannerisms, and wink-wink expressions are inherent skills — they are not learned.

I would love to sit around drinking wine with Barack and Michelle! We’d have a blast!

Their attack lines against former President Donald Trump were spot on. Other speakers from last night included Illinois Gov. J.B. Pritzker, second gentleman Doug Emhoff, and former Trump press secretary Stephanie Grisham. They also received howls.

Below are some of the best lines delivered from the rostrum on the second night of the Democratic Convention. If you were thinking about tuning into a network comedy last night, the better choice for laughs would have been to click on the cable channels covering the convention speakers.

“Who’s going to tell him that the job he’s currently seeking might just be one of those ‘Black jobs’?” Michelle Obama.

When Donald Trump starts talking about immigrants taking “Black jobs,” while it’s racist and disgusting, it also opens the door to humorous fodder. The absolute absurdity of claiming there are Black jobs is silly and stupid, and Michelle Obama nailed the line perfectly.

"She understands that most of us will never be afforded the grace of failing forward. We will never benefit from the affirmative action of generational wealth," Michelle Obama.

Trump hates, hates, hates anyone questioning this wealth and the fact that his father gave him millions of dollars to start his flailing flat career. And watching Trump tie himself in knots trying to explain affirmative action is like watching Houdini wiggle around in a water box.

"Not only do we have massive energy at our convention, we've got a hell of a lot more energy at where they had their convention.Oh, that one guy's going to be so sad tonight,” Tim Walz.

Delivered from Milwaukee last night during a joint appearance with Vice President Harris in the chuck-full venue where the GOP convention took place, Walz knows how sensitive Trump is to crowd size and crowd enthusiasm. While it’s weird and clearly not a major concern for voters, it is an obsession with the narcissistic Trump.

“There’s the childish nicknames, the crazy conspiracy theories, this weird obsession with crowd sizes,” Barack Obama.

Ok, Obama piles on about crowd size, but being the master comic that he is, he spread his hands just a bit apart and looked down at them with a glint in his eye. Was Obama referring to something else Trump is highly sensitive about?

“Take it from an actual billionaire, Trump is rich in only one thing: stupidity," J.B. Pritzker.

A double whammy by the billionaire governor of Illinois. Questioning Trump’s money - he claims to be a billionaire but many others say otherwise - and his “stable genius” are two ways that make Trump rail and wallow on Truth Social.

“We do not need four more years of bluster and bumbling and chaos. We have seen that movie before, and we all know that the sequel is usually worse,” Barack Obama.

When asked if he considered himself a “star” during the E. Jean Carroll deposition, Trump replied, "I think you can say that, yeah.” Trump also claims that he, paraphrasing here, put NBC on the map with The Apprentice. Knocking Trump, who is probably a D-lister, makes his skin crawl.

“I am the only person stupid enough to speak after Michelle Obama,” Barack Obama.

Not about Trump, but what a great line and a way to curry favor with your wife.

"For generations, people debated when to call the person you're being set up with. And never in history has anyone suggested 8:30 a.m." Doug Emhoff.

Same rules above apply here, Plus, I gave you two breaks from Trump, and now back to our regular programming.

“I saw him when the cameras were off … Trump mocks his supporters. He calls them basement dwellers,” former Trump press secretary Stephanie Grisham.

I can’t wait to see someone pick up the term “basement dwellers” and use it in a campaign ad that demonstrates the way Trump feels about his base.

“The other day, I heard someone compare Trump to the neighbor who keeps running his leaf blower outside your window every minute of every day,” Barack Obama.

Wow, Trump has often been referred to as a blowhard, but as a leaf blower at your window…priceless. Obama owes 10% royalty fees to the person who told him that since I see that as a wildly popular Meme.

“Donald hasn’t been in a grocery store since his first bankruptcy. Illinois invested in clean energy and the jobs it brings. Donald claimed that windmills in the ocean made the whales “a little batty.” J.B. Pritzker.

This line is flawless in the way that shows Trump is out of touch with the needs of regular people, and that he is bats**t crazy.

“We don’t have the luxury of whining or cheating others. If we see a mountain in the way, we don’t expect an escalator to take us to the top,” Michelle Obama.

“He has not stopped whining about his problems since he rode down that golden escalator nine years ago,” Barack Obama.

Now this is where the George Burns and Gracie Allen comparison shows most. Both the Obamas going after that staged, manufactured, and whacked elevator ride Trump took when he declared his candidacy for president in 2015.

“You know what I’m talking about? It’s the contagious power of hope!” she said. “The exhilaration of once again being on the cusp of a brighter day… America, hope is making a comeback,” Michelle Obama.

The line has nothing to do with Trump, and everything to do with how Kamala Harris and Tim Walz are bringing hope back versus the doom and gloom of Trump and Vance. Indeed, Harris is picking up the baton of hope being passed to her by Burns and Allen,..err, Barack and Michelle.

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John Casey

John Casey is senior editor of The Advocate, writing columns about political, societal, and topical issues with leading newsmakers of the day. The columns include interviews with Sam Altman, Neil Patrick Harris, Ellen DeGeneres, Colman Domingo, Jennifer Coolidge, Kelly Ripa and Mark Counselos, Jamie Lee Curtis, Shirley MacLaine, Nancy Pelosi, Tony Fauci, Leon Panetta, John Brennan, and many others. John spent 30 years working as a PR professional on Capitol Hill, Hollywood, the Nobel Prize-winning UN IPCC, and with four of the largest retailers in the U.S.
John Casey is senior editor of The Advocate, writing columns about political, societal, and topical issues with leading newsmakers of the day. The columns include interviews with Sam Altman, Neil Patrick Harris, Ellen DeGeneres, Colman Domingo, Jennifer Coolidge, Kelly Ripa and Mark Counselos, Jamie Lee Curtis, Shirley MacLaine, Nancy Pelosi, Tony Fauci, Leon Panetta, John Brennan, and many others. John spent 30 years working as a PR professional on Capitol Hill, Hollywood, the Nobel Prize-winning UN IPCC, and with four of the largest retailers in the U.S.