11 Jokes I Love From 11 White House Correspondents Dinners

As a comedy writer and political obsessive, The White House Correspondents Dinner was once my Super Bowl, Oscars, and Christmas all rolled into one bizarre evening.

Traditionally, the President of the United States tells jokes — like a funny and generally better State of the Union speech — and the featured comedian has the unenviable task of following the President. The comedian is tasked with delivering a monologue that somehow appeals to a crowd of powerful people who are posturing to look good in front of the other powerful people.

Oh, and universally forgotten in the whole process is that the dinner is supposed to be a celebration of the First Amendment, a tribute to journalism, and a fundraiser for the WHCA itself as well as for scholarships for journalism students. But once those necessities are dispensed with, everyone can get on with their evening.

With the President in plain view, the comedian can try to pander and appeal broadly, or go rogue and speak truth directly to power. It’s fascinating to see what comedians do with this opportunity.

Few are asked to come back, and none can expect to be in front of that exact crowd again — the President changes (and, barring changes to the 22nd Amendment, will continue to do so at least octo-annually), the mood of the country shifts, the power players have children who become the new power players — which means that no matter the approach, every comedian who speaks at this dinner is given a one-night-only megaphone. What they do with it speaks volumes.

1995 — Conan O’Brien

Pat Buchanan is also in the race. When Pat Buchanan announced his candidacy, some people — and this is kind of ugly — some people ran onto the stage carrying signs that read ‘Pat Buchanan is a racist.’ And those were his supporters!

I love a joke where the final word of the punchline recontextualizes the setup. Conan uses imagery, describing the people and the signs and writing, so that you build up a visual in your head…only to have him pull the rug out from under you when you realize he’s describing supporters.

He also touches upon an idea here that is particularly poignant in our current era: racism can be the point of political action, not just an unfortunate side effect. He alludes to the idea that if you don’t agree on a basic political premise (in this case, “Racism is bad”), it’s hard to get anywhere in political discussion.

1997 — Jon Stewart

Rosie O’Donnell was the President’s first choice to be here this evening, and she withdrew, citing a nasty and brutal confirmation process. I wasn’t even the second choice — Dennis Miller was the second choice. But he got hung out by an illegal nanny technicality. But isn’t that what the confirmation process is all about, here in Washington: weeding out the truly qualified to get to the truly available?

This joke accomplishes four things at once.

It acknowledges what the audience is thinking: “Who is Jon Stewart?” (It’s important to note that he was two years away from hosting The Daily Show.)

It is self-deprecating, a signature approach Jon Stewart employs to endear himself to the crowd.

It is a textbook example of mapping: Jon outlines the selection process for the WHCD comedian as if it’s a nomination that has to be confirmed by the Senate, which also makes it topical and opens the door to a lot of comedy specifics.

But my favorite part about this joke is the connection it makes at the end: “weeding out the truly qualified to get to the truly available” is such a funny phrase that semi-accurately describes both the WHCD process and Washington in general. It’s also safe to rip on the vague concept of Washington in front of a bunch of people who all like to individually believe they’re exceptions to the rule.

2000 — Jay Leno

See, I wish Trump would’ve run. Trump was the only candidate that never admitted to experimenting with drugs — he said he never, ever did drugs. But actually, Trump did say he came close to doing cocaine one time. But when he leaned over, and he saw his reflection in that mirror, he realized ‘it doesn’t get any better than this.’

Okay, I’m not really a huge Jay Leno fan (I’m still salty about the 2010 Tonight Show with Conan O’Brien conflict), but I love looking at old “What if Trump ran for President” jokes and seeing how they do — or don’t — hold up.

I think this one actually does! Why? Because it focuses in on a premise that isn’t done to death, but that is still a tidbit about Trump that is, as far as we know, true: he has never done drugs.

Where other jokes about Trump being President became stale almost immediately (“he puts his name on buildings…what if he put his name on the White House???”), this one succeeds because it digs a little deeper and explores new territory (especially for 2000). A little research goes a long way!

So then Jay gets to the punchline through the tried and true comedy philosophy: “If this is true, then what else is true?” We know that Trump hasn’t done drugs. Which means he might have turned some down if given the opportunity. One of the wildest drugs he could have reasonably turned down is cocaine. And if we visualize what that scenario might have looked like…he’s faced with his reflection — which directly connects with Trump’s narcissism.

Explaining the joke ruins it, of course, but sorry, that’s what you came here for!

2002 — Drew Carey

You know what I do when I watch the news now? I turn the news off, I get out my Bible, I turn to the Book of Revelations, I start just checking stuff off. ‘Got it, got it, need it, got it, got it, need it…red dragons…seven horns…ten crowns…Ozzy Osbourne, America’s favorite TV dad…

Drew Carey was selected for the first WHCD after 9/11, when DC and the nation as a whole were anxious, sensitive, and on edge — the perfect mood for a comedy set!

This joke is a great example of reading the room. There’s an obligation to acknowledge the fear and terror that is hanging over society…but you don’t want to be insensitive about it. What could be a safer bet than invoking the notion that the Bible was right all along? Throw in a pop culture reference at the end and you’ve got a good example of a straight-down-the-middle joke that works even in a tough situation.

2006 — Stephen Colbert

I believe the government that governs best is the government that governs least, and by these standards, we have set up a fabulous government in Iraq.

Hoo baby. A lot of ink has been spilled about this particular WHCD performance — so I won’t be the zillionth person to analyze its overall impact. Suffice to say, it is one of the bravest comedic monologues ever delivered, and it put the WHCD and Colbert on the map for many (or at least, myself).

This joke encapsulates the power of the performance as a whole. Delivered in character as a bloviating conservative, Colbert uses the conceit of praising George W. Bush to roast him in a fresh and surprising way.

It’s also a powerful example of the importance of placing your reveal at the very end of a joke. Up until the word “Iraq,” the joke is borrowing exactly from conservative talking points. But with “Iraq” at the end, it becomes a devastating critique of both conservative ideology and Bush’s foreign policy.

2008 — Craig Ferguson

No disrespect to the Canadians, I love ’em, but to me, Canada, it’s not the party…it’s the apartment above the party. Do you know what I’m saying? It’s like it’s nice, it’s good, it’s well-decorated, but it’s the apartment above the party. I mean we’re down here…[CRAIG DANCES]…and they’re up there goin’ ‘can you keep the noise down? We’re trying to be polite and wear knitwear up here; keep the noise down!’ And we’re like, ‘oh come to the party, Canada!’ And they’re like ‘we weren’t invited.’ We’re like ‘Mexico wasn’t invited — they came — come to the party!’

This is a fun act-out that subtly takes advantage of Craig’s identity as a recent American immigrant. (Craig is originally from Glasgow, Scotland, and don’t worry — his monologue gets plenty of mileage out of that.)

It answers a funny “what if?” question about what Canada, the United States, and Mexico would be like as apartment neighbors — and Craig has some credibility to make these observations as someone who has been to all three countries, without the bias of being from any of them. Personification is a good way to come up with evocative material; I love the idea of Canada being stuffy and polite, the United States being loud and outgoing, and Mexico being wild and spontaneous — even if those caricatures play on stereotypes a bit.

2009 — Wanda Sykes

This is amazing, you know…the first Black President. (I know you’re biracial, but) the first Black President…that’s unless you screw up. And then it’s gonna be ‘what’s up with the half-white guy, huh?’

Speaking of identity, booking a Black woman as the comedian for the first WHCD for the first Black President opened the door for some special jokes and commentary that could only be told by a Black speaker at that particular moment in history. The above is one of them.

First, I love the way this is set up. It’s important to note that the President is biracial for the joke to work. But Wanda doesn’t just mention it — she squeezes an extra laugh in by including it as a dismissive aside, recognizing the way that the media (and the public at large) glossed over Obama’s biracial identity.

Then, she warns the President about the scenario where the Black community would abandon him — a really funny premise that can most credibly be explored by a Black speaker.

2011 — Seth Meyers

Donald Trump said recently he has a great relationship with the Blacks…though unless ‘the Blacks’ are a family of white people, I bet he’s mistaken.

This joke plays upon a true, idiosyncratic tendency of Donald Trump: his endless insistence that “the Blacks” love him — a rare statement that in its wording alone proves itself to be untrue. If “the Blacks” truly loved him, a Black person would have advised him to stop saying “the Blacks” a long time ago.

Seth does some great wordplay here that uses Trump’s bizarre phrasing against him, characterizing him as someone who only has appeal among white people, despite Trump’s claims to the contrary.

Trump was in the audience for this joke, and it is sometimes said that Meyers and Obama’s attacks on him at this dinner are part of what motivated him to run for President. I’ll let you decide if the above joke is funny enough to justify all that’s happened since.

2016 — Larry Wilmore

C-SPAN, of course, is carrying tonight’s dinner live…which is ironic because most of their viewers aren’t. It’s true guys — C-SPAN is the number one network among people who died watching TV and no one’s found them yet. It is good to be on C-SPAN…I’m glad I’m not on your rival network, NO INPUT — HDMI1.

I don’t know how I’ve managed to get this far into a WHCD retrospective without invoking C-SPAN — the public affairs network that broadcasts the dinner every year. Mocking the earnest, low-viewership broadcaster is a time-honored tradition, and Larry Wilmore did it best.

The first half of this joke is a fantastic example of heightening: we know that C-SPAN has low viewership, and that the few who do watch it are disproportionately older…so if you take that to the furthest logical extreme, you’ve got this shocking and dark but hilarious image.

The second half of this joke is just raw, unfiltered silliness. I really enjoy jokes about demotion — which is to say, it tickles me to think C-SPAN has such low ratings that it’s more comparable to the error message you get when you hit the wrong input button on your remote than a television network.

2017 — Hasan Minhaj

A lot of people in the media say that Donald Trump goes golfing too much…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. 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.’

In 2017, Hasan Minhaj became the first comedian in decades to have to tell jokes without the President there, since Trump opted out of attending. And as an Indian-American Muslim, Minhaj was also tasked with “representing” a demographic group that the President had targeted throughout his 2016 campaign and the beginning of his presidency.

In his monologue, Minhaj claimed that he was “explicitly told not to go after the administration” — but of course, that’s completely unreasonable. The comedian always makes fun of the President at the WHCD, and it would have been awkward for the President’s conspicuous absence to go unacknowledged.

So yes, Minhaj mocks “the elephant not in the room,” but he also takes the opportunity to address the media directly, almost taking the tone of a hushed side conversation while the President’s not listening — even though he was almost certainly listening from somewhere.

Minhaj starts this joke with a sentiment that I tend to share, which is that objections about Trump’s lack of decorum, laziness, addiction to Twitter, and incompetence — while all based on truth — miss the greater threat, which is his evil ideology and destructive tendencies.

So already, I’m on board with the joke. But then Minhaj takes it one step further by diving into a list of evocative, hilarious specifics outlining how to keep Trump distracted for four years. None of them are actually practical ideas, of course, but because Minhaj has already clearly outlined a true sentiment, the point gets across even with ridiculous examples.

Finally, he closes with some memey slang in “Take the W,” tying the joke together and giving it a little extra topical punch.

2018 — Michelle Wolf

You guys gotta stop putting Kellyanne [Conway] on your shows! All she does is lie! If you don’t give her a platform, she has nowhere to lie! 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.

It was not easy to pull just one joke from this routine. If you can only watch two WHCD routines in full, I would recommend this one and Colbert’s for their sheer brazen gutsiness; Colbert’s is the only other monologue that generated a comparable amount of controversy.

What’s odd is why Wolf’s routine was controversial. Wolf got criticized for saying Sarah Huckabee Sanders “burns facts and then she uses that ash to create a perfect smokey eye.” This was seen as a dig at Sanders’s makeup, when in fact it was a compliment to her makeup and a dig at her steadfast commitment to the art of deceit.

What I love about the joke I selected is that it easily could have been the headline joke that got Wolf in trouble, and she seems to know it. It’s a misdirect about taking Kellyanne Conway’s platform away from her that ends with invoking the idea of Conway under a tree.

Before the audience can even fully react to the joke, Wolf clarifies: “I’m not suggesting she gets hurt — just stuck.” I like the joke well enough without the follow-up line, but this last sentence does a lot of funny-lifting.

It saves Wolf from the tedium of being accused in bad faith of placing a death-wish on Kellyanne Conway for the rest of her career. And in making the clarification, she’s also subtly referencing the sensitivity of the room and the event in general. But also, in specifying the image, she makes the joke funnier — who wouldn’t want to see their enemies stuck (but ultimately safe!) under a tree?

Finally, taking a page from the Brian Agler school of comedy, words bookended with hard consonants are inherently funny for reasons that only the Gods can understand. “Stuck” is funny, people!

As of 2019 at least, Michelle Wolf is the WHCD-slayer. Since her unflinching performance, the White House Correspondents Association has not booked another comedian for the show, and the President has continued not to attend. As a big fan of the intersection of politics and comedy, I hope both of these trends revert back to the mean.

After all, most people know the WHCD as the event where the president and a comedian tell jokes. So if a White House Correspondents Dinner takes place in a forest…and no president or comedian shows up to tell jokes…does it trend on Twitter?

Chandler Dean

In “Orations Worth Ovations,” professional speechwriters analyze great speeches (real or fictional, historic or personal) and explain what makes them so good.

Follow Chandler and West Wing Writers on Twitter.

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A progressive communications-strategy firm led by former Clinton, Obama, and Biden Administration speechwriters.