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The funniest presidential moments in modern history



The president of the United States has the most serious job in the world; however, it doesn’t come without its gaffes and humorous moments.

As the leader of the free world, the commander-in-chief is responsible for navigating a range of issues both domestically and internationally, but there’s nothing like seeing the world of politics collide with comedy – even when the said moment wasn’t intended to make you chuckle.

Here’s a roundup of theGrio’s funniest presidential moments in modern history.

Obama calls Kanye West a ‘jackass’

Rarely do U.S. presidents comment on major pop culture events, but after Kanye West’s controversial and viral moment interrupting Taylor Swift’s acceptance speech at the 2009 MTV Video Music Awards, then-President Barack Obama chimed in with his two cents. 

“He’s a jackass,” said Obama on a hot mic during an off-the-record moment ahead of a television interview with CNBC. Moments later, America’s first Black president appeared to realize his off-color remark could make headline news.

“Now, all this stuff…,” said Obama, as he gestured his hand to suggest the comment was off the record. But as any president knows, what’s said to the press – even when off the record – can end up in news publications and on television airwaves.

Despite Obama’s efforts to keep the comment at bay, ABC reporter Terry Moran tweeted it out. Though it was quickly removed, it had already gone viral around the world. Thankfully for Obama, the “jackass” comment didn’t turn out to be a controversial opinion as many Americans at the time appeared to agree. Over a decade later, it would not be surprising if many still held that sentiment about Mr. West.

Biden caught on hot mic saying ‘Big f–king deal’

In another hot mic moment that ended in viral infamy in 2010, then-Vice President Joe Biden dropped the F-bomb to describe the historic nature of President Barack Obama’s landmark health care law dubbed “Obamacare.” While introducing President Obama before giving his remarks at the White House on the passage of the Affordable Care Act, Biden whispered to the president over loud applause, “This is a big f—king deal.”

Indeed, the law was a big deal as it established a historic overhaul of health care in the United States and expanded insurance to more than 20 million people. Biden apparently couldn’t contain his excitement for the prospect of uninsured Americans getting access to quality and affordable health care.

During a White House ceremony commemorating the 13th anniversary of Obamacare in March, President Biden welcomed Obama back to the White House for the first time since leaving office. Referencing his now infamous hot mic moment, President Biden made clear: “I stand by the fact that it was a big deal.”

Obama roasts Trump during White House Correspondents dinner

Who could forget the time Donald Trump was roasted by President Barack Obama at the 2011 White House Correspondents’ Dinner?

After months of leading the racist conspiracy theory that Obama was not born in the United States and thereby ineligible to serve as U.S. president, President Obama was face-to-face with Trump on political journalism’s biggest night. 

Taking advantage of the dinner’s tradition of using comedy to speak to Washington’s most pressing issues, Obama took to the podium to address the birtherism controversy head-on. After playing the famous birth scene of Simba in “The Lion King,” President Obama said, “No one is prouder to put this birth certificate matter to rest more than the Donald.”

He continued, “That’s because he can finally get back to focusing on the issues that matter, like did we fake the moon landing? What really happened in Roswell? And where are Biggie and Tupac?”

Obama also poked fun at what at the time seemed improbable: Trump run’s for president. “He certainly would bring some change to the White House,” said Obama as he displayed a doctored photo of a revamped Trump White House that included a hotel and casino suite and women in bathing suits inside a pool on the front lawn. 

“All kidding aside,” he added, “Obviously, we all know about your credentials and breadth of experience.” 

President Obama later referenced an episode of Trump’s then-television hit show “Celebrity Apprentice,” in which Trump had to painstakingly decide which celebrity to fire. 

“These are the kinds of decisions that would keep me up at night,” Obama joked as the crowd laughed and an uncomfortable Trump grimaced.

As Trump confidant and former advisor Roger Stone put it, Obama’s roasting of Trump likely motivated the reality TV star to run for office. Of course, we now know the irony is that Trump would ultimately succeed Obama as the 45th president of the United States.

Pelosi outshines Trump’s State of the Union

Former President Donald Trump can thank former House Speaker Nancy Pelosi for generating what was probably the most viral moment of his presidency. During his 2020 State of the Union address, Trump was arguably outshined by his Democratic foe.

As Trump delivered his message to a joint session of Congress and the American public, Pelosi, who sat directly behind him on the House dias, visibly disapproved of his remarks based on countless facial expressions that became a source of levity for viewers. 

But nothing was more comical than Pelosi’s infamous handclap of approval of Trump for his call for “compromise” and “the common good.” The moment, as well as Pelosi shockingly tearing up the transcript of Trump’s speech, became an instant viral sensation online, sparking millions of memes and reactions.

When asked why she ripped the printed speech of Trump, Pelosi explained, “Because it was a manifesto of mistruths.”

However, despite her clap of approval for Trump being interpreted as condescending, Pelosi made clear, “It wasn’t sarcastic.” Of course, it didn’t stop the internet from using it for a good laugh.

Bush dodges shoes thrown at him

It may be hard to remember how unpopular former President George W. Bush was given his close relationship with the Obamas and the overshadowing of another unpopular Republican president, Donald Trump. However, by the end of his 8-year presidency, Bush had an approval rating as low as 25%. 

The disdain for Bush and his policies was shared abroad, as evidenced by the infamous moment when an Iraqi journalist threw his shoes at the U.S. president during a press conference in Baghdad with the then-Iraqi prime minister. Bush was unharmed as he quickly ducked to avoid contact, but it didn’t stop the moment from being the butt of jokes around the globe.

The journalist, Muntadhar al-Zaidi, said he threw his shoes at Bush in protest of the U.S. military invasion of Iraq. Though he became an overnight international celebrity, Zaidi was ultimately convicted and jailed for nine months. Twenty years later, Zaidi said he only had one regret: “[I] only had two shoes.”


Gerren Keith Gaynor

Gerren Keith Gaynor is a White House Correspondent and the Managing Editor of Politics at theGrio. He is based in Washington, D.C.

TheGrio is FREE on your TV via Apple TV, Amazon Fire, Roku and Android TV. Also, please download theGrio mobile apps today! 


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