The annual White House Correspondents’ Association Dinner, where journalists, politicians, and celebrities don their best attire and pretend to be friends, is a notoriously difficult event to emcee. Presidents try to get big laughs to appear funny, the crowd is famously difficult for comedians to please, and the host has a difficult balancing act to pull off.
The jury is still out on Joel McHale’s brutal takedown of Washington in 2014. Conan O’Brien played it too safe his second time hosting the event in 2013. And Wanda Sykes caused a stir with her 2009 partisan performance.
Tonight’s dinner will be especially challenging for The Daily Show’s Hasan Minhaj. The man who is usually at the heart—or the butt—of the jokes will not be present. US president Donald Trump and his staff have decided to skip the event. (The last president to miss it was Ronald Reagan in 1981. He had been recovering from a gunshot.)
Say what you will about the White House correspondents’ dinner, also known as the ”nerd prom,” which has been accused of making the factions inappropriately cozy, but there were times when it was actually, hilariously funny.
The start of comedy
The White House correspondents’ dinner began start shifting into the A-list affair it is today in 1980s. And, in 1983, political satirist Mark Russell’s performance led the tradition of making comedy the star of the evening. Prior to that, comedians like Bob Hope emceed the event, but there were also musical acts and other performances, like a variety show.
Russell hit journalists, newspapers, and politicians from both sides of the aisle in rapid-fire succession during his performance, according to Washington Post’s coverage (paywall) of the event.
“A couple of weeks ago,” Russell said, “the president was talking about El Salvador and he said, ‘We are not talking about nutmeg here but about the security of the United States.’ You know what they say: Today the nutmeg, tomorrow paprika. Remember, when you are president, you have to be a man for all seasons.”
This was before C-Span televised the event.
Who the hell is Jon Stewart? (1997)
Stewart, before his The Daily Show days made him an icon, was the White House Correspondents’ Association’s third choice to emcee the event in 1997, after Rosie O’Donnell and Dennis Miller declined. But Stewart did not disappoint.
His jokes, if a tad outdated now, captured the sardonic sarcasm the comedian became known for: “Isn’t that what the confirmation process is in Washington? Weeding out the truly qualified until you get the truly available?” His performance starts around the 43-minute mark.
Obama’s mic drop (2016)
Larry Wilmore skewered the media when he hosted the White House correspondents’ dinner in 2016, but it was Barack Obama who, in his final months in office, got the biggest laughs of the night. “In my final year, my approval ratings keep going up,” Obama said. “The last time I was this high, I was trying to decide on my major.”
He lambasted the GOP, including congressional republicans, GOP chairman Reince Priebus (“Glad to see you that you feel that you’ve earned a night off…The Republican Party, the nomination process, it’s all going great”), and, of course, Trump, who didn’t attend that year, either (“What could he possibly be doing instead? Is he at home, eating a Trump Steak, tweeting out insults to Angela Merkel?”).
He also showed us how foolishly confident the Democrats were this time last year. “Next year at this time someone else will be standing here in this very spot,” Obama said, “and it’s anyone’s guess who she will be.”
Stephen Colbert demolishes George W. Bush (2006)
Then there was 2006, when Stephen Colbert roasted George W. Bush. He wasn’t mean-spirited, but he sure didn’t hold back either.
“I know there’s some polls out there saying that this man has a 32-percent approval rating. But guys like us, we don’t pay attention to the polls. We know that polls are just a collection of statistics that reflect what people are thinking in ‘reality.’ And reality has a well-known liberal bias.”
That statement is as applicable now as it was then.
Laura Bush has jokes (2005)
In 2005, headliner Cedric the Entertainer even had George W. Bush’s national security advisor Condoleezza Rice laughing heartily with his cracks about her first name.
“I love that name, Condoleezza. It’s so soulful,” said Cedric the Entertainer, whose real name is Cedric Kyles. “You know, she’s very professional, but Condoleezza—come on, right there. Condoleezza. It’s two people, though. You know, the name is broken down. There’s the Condi, who’s—that’s the person you see on television with, you know, the nice hair and very professional. Then there’s the Leezza. She the one with her hair wrapped up on the phone with her girlfriend watching BET…”
But it was the president’s wife, Laura Bush, who stole the show with her “desperate housewife” routine.
Obama and Seth Meyers tag team Trump (2011)
Trump has taken abuse at White House correspondents’ dinners before. But the 2011 event has gone down in infamy. Obama tore into Trump that year to get revenge for the birther conspiracy.
“No one is happier, no one is prouder to put this birth certificate matter to rest than the Donald,” Obama said. “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 went on about Trump for a full five minutes (paywall). And, to settle the matter, he brought along his own birthing video—a clip from Disney’s The Lion King.
Then, after Obama had his fill, the featured comedian, Seth Meyers, finished Trump off. “Donald Trump has been saying that he will run for president as a Republican—which is surprising, since I just assumed that he was running as a joke.”
The joke is on Meyers now.