Obama's 7 best zingers at D.C. insiders' annual dinner
But when he does, he goes all out, taking jabs at himself, the Republicans (unofficially) running for president, and even Hillary Clinton.
Here are the top seven moments from Obama's joke-filled address to the crowd of insiders:
That's because Obama was placing his trust in something he had quite a bit of experience with in his teens.
"I'm not saying I'm any funnier. I'm saying weed is now legal in D.C."
"You start getting crankier as you get older. Next week, I'm signing an executive order to get off my lawn," Obama joked, making light of the controversy over his use of executive actions.
Pointing out that "getting older changes you," the President, who's known for drinking tea, explained that "coffee really disagrees with me these days."
"Which is why John Boehner just invited coffee to address the joint House," Obama joked, less than two weeks after Israeli Prime Minister Benjamin Netanyahu addressed Congress at Boehner's invitation.
"Just a few years ago, I could never imagine ever being in my fifties. And when it comes to my approval ratings, I still can't."
"Think about how things have changed since 2008. Back then, I was the young tech-savvy candidate of the future," Obama said. "Now I'm yesterday's news and Hillary has got a server in her house."
"I didn't even know you could have one of those in your house," he continued. "I am so far behind. Did you know that? I would have gotten one."
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Obama's 7 best zingers at D.C. insiders' annual dinner
- For the GOP majority to survive 2026, Trump must do something Obama could not - CNN - September 21st, 2025 [September 21st, 2025]
- Karoline Leavitt says Obama 'has no idea what he's talking about' after Kimmel comments - Fox News - September 21st, 2025 [September 21st, 2025]
- President Obama Gave A Hilarious Update On That Infamous Tan Suit - Yahoo - September 21st, 2025 [September 21st, 2025]
- Stupid AF: Antonio Brown slams Barack Obama over Jimmy Kimmel cancellation and media freedom debate - The Times of India - September 21st, 2025 [September 21st, 2025]
- White House rips Barack Obama for suggesting Trump had a hand in Jimmy Kimmels show being yanked - AOL.com - September 21st, 2025 [September 21st, 2025]
- Obama says the U.S. is at an inflection point after Kirks killing and Trump has divided the country - Butler Eagle - September 21st, 2025 [September 21st, 2025]
- After Kirks killing, Obama says the nation is in a political crisis - The Seattle Times - September 21st, 2025 [September 21st, 2025]
- Obama responds to the assassination of Charlie Kirk - CNN - September 19th, 2025 [September 19th, 2025]
- After National Tragedies, Obama and Trump Are a Study in Contrasts - The New York Times - September 19th, 2025 [September 19th, 2025]
- Obama says the Trump administration has taken cancel culture to a 'dangerous level.' See how politicians are reacting to Kimmel's suspension. -... - September 19th, 2025 [September 19th, 2025]
- Obama condemns horrific Kirk shooting, but defends the right to criticize the founder of Turning Point USA - Politico - September 19th, 2025 [September 19th, 2025]
- Presidents Trump, Obama react to ABC's Jimmy Kimmel decision - LiveNOW from FOX - September 19th, 2025 [September 19th, 2025]
- After national tragedies, Obama and Trump are a study in contrasts - eKathimerini.com - September 19th, 2025 [September 19th, 2025]
- Ex-Obama staffer: If Jimmy Kimmel returns to air, he needs to kick the s--- out of Trump - NJ.com - September 19th, 2025 [September 19th, 2025]
- Obama Breaks Silence on Disneys Jimmy Kimmel Suspension: Warns of Escalating Media Suppression - disneydining.com - September 19th, 2025 [September 19th, 2025]
- Video of Barack Obama Responding to Heckler Takes Off Online - Newsweek - September 19th, 2025 [September 19th, 2025]
- People are comparing Obama and Trumps messages on Charlie Kirk shooting - and they're concerned - Indy100 - September 19th, 2025 [September 19th, 2025]
- Obama Says Charlie Kirks Ideas Were Wrong, But What Happened to Him Was a Tragedy - Yahoo - September 19th, 2025 [September 19th, 2025]
- President Obama accuses the Trump administration of 'government coercion' after ABC takes Jimmy Kimmel off the air - Fortune - September 19th, 2025 [September 19th, 2025]
- Barack Obama recalled one of the darkest moments of his presidency when Dylann Roof, a white supremacist, killed nine Black people in South Carolina.... - September 19th, 2025 [September 19th, 2025]
- WNBA star responds to 'scary' Obama accusations against Trump - Daily Express US - September 19th, 2025 [September 19th, 2025]
- Barack Obama Says Media Companies Need to 'Start Standing Up' to Trump in Wake of Kimmel Suspension - TheWrap - September 19th, 2025 [September 19th, 2025]
- Antonio Lpez named 202526 Obama Foundation Leader - The Almanac - September 19th, 2025 [September 19th, 2025]
- Transcript: President Barack Obama in Conversation with Steve Scully - Jefferson Educational Society - The Singju Post - September 19th, 2025 [September 19th, 2025]
- Barack Obama On Jimmy Kimmel Being Pulled Off Air: Media Companies Need To Start Standing Up - VIBE.com - September 19th, 2025 [September 19th, 2025]
- Obama warns of a 'political crisis' in the wake of Kirks killing - USA Today - September 19th, 2025 [September 19th, 2025]
- President Obama's awful take on the Charlie Kirk tragedy - Facebook - September 19th, 2025 [September 19th, 2025]
- Kimmel 'fired for lack of talent', Trump says, as Obama decries 'government coercion' - Sky News - September 19th, 2025 [September 19th, 2025]
- Obama Points Finger at Violent Rhetoric from the White House that Incites Hate - La Voce di New York - September 19th, 2025 [September 19th, 2025]
- Obama Breaks His Silence After the Death of Charlie Kirk And He Had a Few Things to Say About Trump Too - The Root - September 19th, 2025 [September 19th, 2025]
- After Kirks Killing, Obama Says the Nation Is in a Political Crisis - The New York Times - September 17th, 2025 [September 17th, 2025]
- Obama tackles 'controversial topics' in visit to Erie with nation at inflection point - Buffalo Toronto Public Media - September 17th, 2025 [September 17th, 2025]
- Obama condemns Charlie Kirk's killing, says tragedy being used to 'silence discussion' - Erie Times-News - September 17th, 2025 [September 17th, 2025]
- Royal Expert Reveals Why a "Serious Row" Erupted When Queen Elizabeth Offered to Personally Greet Barack Obama in Windsor During U.K. Visit... - September 17th, 2025 [September 17th, 2025]
- Former President Barack Obama will make trip to Erie for JES Global Summit - yourerie.com - September 17th, 2025 [September 17th, 2025]
- WATCH: Sean Lafferty live at the Erie Insurance Arena awaiting Obama appearance - yourerie.com - September 17th, 2025 [September 17th, 2025]
- Joe Manchin makes a triumphant return and wastes no time targeting Obama, Biden - NJ.com - September 17th, 2025 [September 17th, 2025]
- Authorities seize truckload of alcohol from Obama Valero gas station after license revoked - WLTX - September 17th, 2025 [September 17th, 2025]
- Eoin Hayes admits wearing brown makeup to dress up as Barack Obama - MSN - September 17th, 2025 [September 17th, 2025]
- Irish politician that dressed as Barack Obama in brown makeup apologizes - Daily Express US - September 17th, 2025 [September 17th, 2025]
- Opinion | Obama makes an about-face on red and blue America - The Washington Post - September 15th, 2025 [September 15th, 2025]
- Artists including Jenny Holzer, Alison Saar and Kiki Smith creating commissions for Obama Presidential Center - The Art Newspaper - September 15th, 2025 [September 15th, 2025]
- T.J. Wilkins and Shanice Will Be Barack and Michelle Obama in New Musical 44 Off-Broadway - Playbill - September 15th, 2025 [September 15th, 2025]
- Why did the Queen's offer to 'pop out and pick up' Barack Obama spark a 'serious row' between Buckingham Palace and the Secret Service? - Daily Mail - September 15th, 2025 [September 15th, 2025]
- This Bavarian Hideaway Has Hosted Obama, Zadie Smith And A Guest List Of Icons Heres What Its Like - SUITCASE Magazine | - September 15th, 2025 [September 15th, 2025]
- SNL wins big for season 50 at the Creative Arts Emmys. Obama, Kimmel and Lamar also take trophies - The Philadelphia Sunday Sun - September 15th, 2025 [September 15th, 2025]
- The Obama Presidential Center Announces a Wave of New Commissions, and Other News - surfacemag.com - September 13th, 2025 [September 13th, 2025]
- Dr. Chris Burton of Union Presbyterian Seminary is announced as a 2025-2026 Obama Foundation Leader - Presbyterian Church (U.S.A.) - September 13th, 2025 [September 13th, 2025]
- Soccer Recap: Barack Obama School for Social Justice Starts Season with Defeat on the Road - MaxPreps.com - September 13th, 2025 [September 13th, 2025]
- Barack Obama Wins Third Emmy for Our Oceans at 2025 Creative Arts Emmys - Blex Media - September 11th, 2025 [September 11th, 2025]
- Barack Obama condemns 'despicable violence' in the shooting of Charlie Kirk - USA Today - September 11th, 2025 [September 11th, 2025]
- Meet the Democratic kingmakers who anoint the next Obama - MSNBC News - September 11th, 2025 [September 11th, 2025]
- IRS issues termination notice to top aide linked to Obama-era Tea Party targeting scandal - Fox News - September 11th, 2025 [September 11th, 2025]
- The Obama Foundation Introduces 2025-2026 Class of More Than 200 Global Leaders - Obama Foundation - September 11th, 2025 [September 11th, 2025]
- Grassley Slams Obama and Biden Administrations for Decade of Taxpayer-Funded Government Weaponization - Senate Committee on the Judiciary (.gov) - September 11th, 2025 [September 11th, 2025]
- Joe Biden, Barak Obama, Kamala Harris, Gavin Newsom and More Democrats React to the Death of Charlie Kirk - Latin Times - September 11th, 2025 [September 11th, 2025]
- From Bernie Sanders to Theo Von: These Democratic Kingmakers Will Anoint the Next Obama - Vanity Fair - September 11th, 2025 [September 11th, 2025]
- Biden and Obama react after the murder of Trump ally Charlie Kirk: This violence has no place in the US, we pray for his family - Gazeta Express - September 11th, 2025 [September 11th, 2025]
- Obama, Kamala Harris, other Democrats condemn the killing of Trump ally Charlie Kirk - Face2Face Africa - September 11th, 2025 [September 11th, 2025]
- Meet the Democratic kingmakers who anoint the next Obama - MSN - September 11th, 2025 [September 11th, 2025]
- 'SNL' wins big for season 50 at the Creative Arts Emmys. Obama, Kimmel and Lamar also take trophies - KOB.com - September 11th, 2025 [September 11th, 2025]
- Charlie Kirk, 31, dead after Utah shooting: Donald Trump, Barack Obama, Kamala Harris and more pay tribute - HELLO! Magazine - September 11th, 2025 [September 11th, 2025]
- SNL, Obama and Kendrick Lamar among winners at the Creative Arts Emmys - The Independent - September 11th, 2025 [September 11th, 2025]
- Obama center construction tab reaches $615M as opening nears - Chicago Tribune - September 9th, 2025 [September 9th, 2025]
- Barack Obama gets an Emmy: List of winners for the awards first round - The Mercury News - September 9th, 2025 [September 9th, 2025]
- In new book, former Obama speechwriter calls on Jews to stand proud for their values - Jewish Insider - September 9th, 2025 [September 9th, 2025]
- 'SNL' wins big for season 50 at the Creative Arts Emmys. Obama, Kimmel and Lamar also take trophies - AP News - September 9th, 2025 [September 9th, 2025]
- Barack Obama wins third Emmy for Netflix documentary Our Oceans at 2025 Creative Arts Emmys - Mint - September 9th, 2025 [September 9th, 2025]
- President Barack Obama Wins His Third Emmy - Deadline - September 9th, 2025 [September 9th, 2025]
- Barack Obama Scores His Third Emmy, Wins for Narrating Our Oceans at 2025 Creative Arts Emmys - People.com - September 9th, 2025 [September 9th, 2025]
- Kendrick Lamar, 2025 Grammys, Barack Obama Win on Night 2 of 2025 Creative Arts Emmys - Billboard - September 9th, 2025 [September 9th, 2025]
- "That's what I do" - When Barack Obama hit a 3-pointer while on the campaign trail for Joe Biden - Basketball Network - September 9th, 2025 [September 9th, 2025]
- SNL, Obama and Kendrick Lamar among winners at the Creative Arts Emmys - Yahoo News Canada - September 9th, 2025 [September 9th, 2025]
- Barack Obama Wins Third Emmy - V103 - September 9th, 2025 [September 9th, 2025]
- Obama Judge Who Blocked Planned Parenthood Defunding Takes Aim at Laken Riley Act - The Daily Signal - September 9th, 2025 [September 9th, 2025]
- 'SNL' wins big for season 50 at the Creative Arts Emmys. Obama, Kimmel and Lamar also take trophies - WSLS - September 9th, 2025 [September 9th, 2025]
- ICYMI: A Reagan Appointee Assesses Reagan, Obama, Biden, and Trump - TAPinto - September 9th, 2025 [September 9th, 2025]
- ESPN Acquires U.S. Rights To Feature Doc Origin: The Story Of The Basketball Africa League Starring Barack Obama & Steph Curry TIFF - Deadline - September 9th, 2025 [September 9th, 2025]
- 'SNL' wins big for season 50 at the Creative Arts Emmys. Obama, Kimmel and Lamar also take trophies - The Sun Chronicle - September 9th, 2025 [September 9th, 2025]
- 'SNL' wins big for season 50 at the Creative Arts Emmys. Obama, Kimmel and Lamar also take trophies - Toronto Star - September 9th, 2025 [September 9th, 2025]