15 of Barack Obama’s funniest moments

Barack Obama is revered for his eloquence and leadership, but his humor is what made him truly relatable. Whether delivering a roast at the White House Correspondents’ Dinner or reading mean tweets with a straight face, Obama’s ability to balance serious leadership with lighthearted moments set him apart. With sharp one-liners and a knack for self-deprecating humor, Obama proved time and again that he could make us laugh as easily as he could inspire us.

Here are some of REVOLT’s picks for Obama’s funniest moments that remind us why he’s not just a great leader but also has major comedic chops and charm.

1. The ‘Thanks, Obama’ meme comeback

Obama embraced internet culture with his playful take on the “Thanks, Obama” meme. In a White House video, he struggled to dunk a cookie into a glass of milk because the glass was too small. After his failed attempt, he deadpanned, “Thanks, Obama.” The moment showed his self-awareness and ability to laugh at himself, further endearing him to a younger audience.

2. His mic drop at the White House Correspondents’ Dinner

At his final White House Correspondents’ Dinner in 2016, Obama ended his speech with an unforgettable mic drop. After delivering a series of hilarious roasts, he closed with, “Obama out,” and literally dropped the mic. The crowd erupted, and the moment instantly became one of the most iconic exits in political history.

3. His dad jokes at the turkey pardon

Thanksgiving wouldn’t be complete without Obama’s corny dad jokes during the annual turkey pardon. One year, he quipped, “Time flies, even if turkeys don’t.” The laughs from Sasha and Malia only added to the hilarity, proving Obama could balance humor with tradition.

4. Slow Jamming the News with Jimmy Fallon

When Obama joined Jimmy Fallon for “Slow Jam the News,” he turned policy discussions into a soulful serenade. Backed by The Roots, Obama smoothly said, “The Affordable Care Act is here to stay,” while Fallon and the band added a sultry vibe. It was equal parts comedic and cool, reminding everyone why Obama’s charisma is unmatched.

5. Trolling Donald Trump at the 2011 Correspondents’ Dinner

At the 2011 White House Correspondents’ Dinner, Obama hilariously roasted Donald Trump, who was in the audience. Mocking Trump’s obsession with the birther conspiracy, Obama said, “No one is prouder to put this birth certificate matter to rest than The Donald — because he can finally get back to focusing on the issues that matter, like whether we faked the moon landing.” The roast left the room in stitches.

6. The Al Green singing moment

At the Apollo Theater, Obama surprised the crowd by singing a few bars of Al Green’s “Let’s Stay Together.” His smooth delivery earned cheers from the audience and praise from Green himself. The impromptu performance became an instant viral moment, proving Obama’s charisma wasn’t limited to speeches.

7. His Jedi mind meld mix-up

During a 2013 press conference, Obama accidentally mixed Star Wars and Star Trek references, saying, “I should somehow do a Jedi mind meld.” He continued his address, while winning over sci-fi fans everywhere with his ability to roll with the mistake and turn it into humor.

8. His roast of Kanye West

When Kanye West announced his presidential run, Obama couldn’t resist poking fun. At a fundraiser, he quipped, “Do you really think that this country is going to elect a Black guy from the South Side of Chicago with a funny name to be president of the United States? That is crazy.” The self-referential joke was both clever and hilarious.

9. The Easter Egg Roll moment

At the 2016 White House Easter Egg Roll, Obama’s playful side was on full display as he helped a child roll an egg across the lawn, comforted a crying child and reading “Where The Wild Things Are.” His ability to bring warmth to even the simplest traditions made moments like these unforgettable.

10. His anger translator with Keegan-Michael Key

At the 2015 White House Correspondents’ Dinner, Obama teamed up with comedian Keegan-Michael Key, who played his “anger translator” Luther. As Obama calmly delivered his remarks, Key hilariously ranted on his behalf. The skit’s perfect comedic timing made it one of the dinner’s most memorable moments.

11. The tan suit controversy

After the media made an uproar over his tan suit, Obama casually referenced the incident with humor. Speaking at a fundraiser, he joked, “I wanted to wear my tan suit tonight, but Michelle said no.” His ability to turn a ridiculous controversy into a punchline highlighted his quick wit.

12. His basketball game expression

During a basketball game, Obama was caught on the Jumbotron eating popcorn. As fans cheered, he gave an exasperated “Can I live?” expression, which instantly became a meme. It was a relatable and funny moment that showed Obama’s unbothered energy.

13. His comeback to the ‘dad jeans’ critique

Obama has faced plenty of ribbing for his so-called “dad jeans,” but he’s always taken it in stride. When asked about it during an interview, he said, “I am a little frumpy. ... Those jeans are comfortable, and for those of you who want your president to look great in his tight jeans, I’m sorry — I’m not the guy. It just doesn’t fit me. I’m not 20.” His unbothered response made him all the more relatable.

14. The ‘Mean Tweets’ episodes

Obama’s “Mean Tweets” appearances on Jimmy Kimmel were comedic gold. Reading out tweets mocking his dad jeans and graying hair, he delivered deadpan responses that stole the show. When a tweet compared him to Nickelback, he replied, “That’s not true. Nickelback is much more popular in Canada.” It was a perfect example of his ability to laugh at himself.

15. The Healthcare.gov plug with Zach Galifianakis

Obama’s “Between Two Ferns” segment with Zach Galifianakis was a masterclass in deadpan comedy. Trading insults with the comedian, Obama weaved in a plug for Healthcare.gov, saying, “What we want is for people to know that you can get affordable healthcare.” The clip became a viral sensation, proving that comedy could be a tool for public policy.