Most humorous and controversial jokes from White House Correspondents Dinners over the years

Here are eight occasions when the funniest and most controversial jokes were made at White House Correspondents Dinners over the years
PUBLISHED APR 28, 2024
Joe Biden, Donald Trump, Barack Obama, and Larry Wilmore have been part of the wittiest and most controversial jokes said during the White House Correspondents Dinners over the years (Getty Images)
Joe Biden, Donald Trump, Barack Obama, and Larry Wilmore have been part of the wittiest and most controversial jokes said during the White House Correspondents Dinners over the years (Getty Images)

8 wittiest and controversial jokes from White House Correspondents Dinners

(Getty Images, C-SPAN screenshot/YouTube)
President Joe Biden mocked Donald Trump at the 2024 White House Correspondents Dinner and Michelle Wolf trolled the latter's aides in 2018 (Getty Images, C-SPAN screenshot/YouTube)

The 2024 White House Correspondents Dinner took place on April 27 at the Washington Hilton Hotel. The annual dinner was a glitzy night of gossip for journalists and government officials, which gave them a break from their usual routine. President Joe Biden used the final White House Correspondents Dinners of his current term to poke fun at his presidential opponent, Donald Trump, amid their bid for a second White House term. Here are eight occasions over the years when the funniest and most controversial jokes were made at the annual event.

1. Joe Biden mocks Trump with 'Stormy weather' jibe in 2024

LOS ANGELES, CALIFORNIA - JANUARY 16: Stormy Daniels attends the XBIZ Awards 2020 on January 16, 202
President Joe Biden mockingly cited Stormy Daniels' name at the 2024 White House Correspondents Dinner (Getty Images)

In the 2024 White House Correspondents Dinner speech, President Joe Biden took a swipe at Donald Trump regarding the ongoing hush money trial. "I had a great stretch since the State of the Union. But Donald has had a few tough days lately. You might call it Stormy Weather," the president said. The mockery stemmed from the criminal trial that started on April 15 against his predecessor for falsifying financial records to cover up a $ 130,000 payment to Stormy Daniels before the 2016 election in exchange for her silence about their alleged sexual encounter.

2. Michelle Wolf burns Trump's press secretary Kellyanne Conway in 2018

Michelle Wolf and Kellyanne Conway at the 2018 WHCD (The Guardian, C-SPAN screenshots YouTube)
Michelle Wolf and Kellyanne Conway at the 2018 White House Correspondents Dinner (The Guardian and C-SPAN screenshots YouTube)

Michelle Wolf brutally trolled Donald Trump's press secretary Kellyanne Conway during the 2018 White House Correspondents Dinner gig. Her mockery was aimed at Conway for communicating the then-president's "alternate facts" to the media. "She has the perfect last name for what she does -- 'Con-way'… You guys have got to stop putting Kellyanne on your shows. All she does is lie. If you don't give her a platform, she has nowhere to lie," Wolf said. "It's like that old saying, if a tree falls in the woods, how do we get Kellyanne under that tree? I'm not suggesting she gets hurt. Just stuck. Stuck under a tree," she added.

3. Michelle Wolf compares Ivanka Trump women's advocacy to 'empty box of tampons' in 2018

( Tasos Katopodis/Getty Images, Getty Images)
Michelle Wolf mocked Ivanka Trump at the 2018 White House Correspondents Dinner (Tasos Katopodis/Getty Images, Getty Images)

Michelle Wolf's 2018 White House Correspondents Dinner performance also took a dig at ex-president Donald Trump's daughter Ivanka Trump. The comedian ridiculed the billionaire's offspring over her unimpressive works for women's advocacy. "There's also, of course, Ivanka. She was supposed to be an advocate for women, but it turns out she's about as helpful to women as an empty box of tampons. She's done nothing to satisfy women. So, I guess like father, like daughter," Wolf quipped.

4. Hasan Minhaj brutally ridicules Donald Trump in 2017

Hasan Minhaj (ABC News screenshot/YouTube)
Hasan Minhaj mockingly addressed Donald Trump's absence at the 2017 White House Correspondents Dinner (ABC News screenshot/YouTube)

Comedian Hasan Minhaj fully used the moment in the 2017 White House Correspondents Dinner when then-president Donald Trump broke the decades-long tradition by not attending the event. Despite his administration's warning not to make jokes in the commander-in-chief's absence, the comedian performed a skit addressing the "elephant in the room". The skit looked into what Trump would be doing when the world was not watching. "A lot of people in the media say that Donald Trump goes golfing too much," Minhaj started. "Which raises a very important question -- why do you care? Do you wanna know what he's not doing when he's golfing? Being president. Let the man putt-putt. Keep him distracted. Teach him how to play badminton. Tell him he has a great body for bobsledding. Play him in tic-tac-toe." He then mocked how the president would prevent war by being distracted. "The longer you keep him distracted, the longer we're not at war with North Korea. Every time Donald Trump goes golfing, the headline should read -- 'Trump Golfing. Apocalypse Delayed. Take the W."

5. Larry Wilmore uses 'N-word' at 2016 WHCD

Larry Wilmore used the N-word at 2016 WHCD (ABC News screenshot/YouTube)
Larry Wilmore used the N-word at the 2016 White House Correspondents Dinner (ABC News screenshot/YouTube)

Larry Wilmore's stand-up at the 2016 White House Correspondents Dinner stirred controversy after he dropped the N-word in front of then-president Barack Obama. "To live in your time, Mr President, when a Black man can lead the entire free world... Words alone do me no justice.... Yo, Barry - you did it, my N-word," The 'Nightly Show' host said. Though it was not well received by many, Obama had a laugh and embraced Wilmore. Following widespread criticism for inappropriately addressing the president, the comedian promised he would never use the racial slur again.

6. Barack Obama introduces his 'anger translator' Luther in 2015

WASHINGTON, DC - APRIL 25: The presidents translator, Luther (L), as portrayed by comedian Keegan-Michael Key, gestures as President Barack Obama speaks at the annual White House Correspondent's Association Gala at the Washington Hilton hotel April 25, 2015 in Washington, D.C. The dinner is an annual event attended by journalists, politicians and celebrities. (Photo by Olivier Douliery-Pool/Getty Images)
The president's translator, Luther portrayed by comedian Keegan-Michael Key, gestures as President Barack Obama speaks at the annual White House Correspondent's Association Gala at the Washington Hilton Hotel on April 25, 2015 (Olivier Douliery-Pool/Getty Images)

During the 2015 White House Correspondents Dinner speech, Barack Obama introduced his 'anger translator' Luther, played by comedian Keegan-Michael Key. Through his physical gestures, including stamping and howling, the new employee conveyed the hidden subtext of Obama's understated speech. "Despite our differences, we count on the press to shed light on the most important issues of the day," the ex-president said, while Key added, "...And we can count on Fox News to terrify old white people with nonsense!"

7. Barack Obama mocks Trump's 'birther' conspiracy theories in 2011

WASHINGTON, DC - JANUARY 20:   President Barak Obama (R) and President-elect Donald Trump smile at t
Barack Obama dismissed Donald Trump's birther conspiracy theory during the 2011 White House Correspondents Dinner (Getty Images)

Barack Obama brutally dismissed Donald Trump's promotion of "birther" conspiracy theories at the 2011 White House Correspondents Dinner. He walked onto the stage with Rick Derringer's song 'Real American' playing in the background and the enormous images of his birth certificate projected in the room. Trump had falsely claimed that Obama was not born in America. "I know that he's taken some flack lately, but no one is prouder to put this birth certificate matter to rest than the Donald," the former president quipped. "And that's because he can finally get back to the issues that matter, like did we fake the moon landing? What really happened in Roswell? And where are Biggie and Tupac?" he asked.

8. Stephen Colbert's savage attack against George W Bush in 2006

Stephen Colbert played an alter ego to defend George W Bish's presidency at the 2006 WHCD (Getty Images)
Stephen Colbert played an alter ego to defend George W Bush's presidency at the 2006 White House Correspondents Dinner (Getty Images)

In 2006, Stephen Colbert portrayed the character of a hotheaded right-wing media pundit at the White House Correspondents Dinner, unleashing a 20-minute brutal attack defending George W Bush's ailing administration. "It's like the movie Rocky. The president is Rocky Balboa, and Apollo Creed is... everything else in the world," he joked. Colbert's alter ego backed the president by calling the president his spiritual kin. "People out there are saying that this man has a 32 percent approval rating! But guys like us, we don't pay attention to the polls," Colbert continued, before adding, "And reality has a well-known liberal bias!"

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