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Obama's Past White House Correspondents' Dinner Monologues Prove He Got Funnier Over Time

This coming Saturday, President Barack Obama will attend his final White House Correspondents' Dinner. The event, held at the Washington Hilton Hotel, will be attended by both Hollywood and Washington elite. The dinner is hosted by the White House Correspondents’ Association, and functions as both an awards show for journalists and a fundraiser to provide scholarships for promising young journalism students. But what everyone's really looking forward to is Obama's monologue. And, videos of Obama's White House Correspondents' Dinner monologues over his eight years as president prove this last one will be epic.

The event has seen a lot of changes since its inception in 1921; according to ABC News, people of color were banned until the 1950s. The entertainment was originally comprised of musical performances, movies and variety shows, and it wasn't until the 1980s that celebrities began attending. Comedy didn't become a staple until 1983. Nowadays, the whole point of the affair, as far as anyone who's not a journalist is concerned, is to watch the president do 20 minutes of stand-up comedy. While Obama started off a little shaky at his first dinner in 2009 (just 110 days into his presidency), by now he's proven that he's got the chops for a comedy career once this whole president thing wraps up. Take a look at his improvement over the years:


Obama's first monologue is probably best left for the hardcore fans. He opens with a clunker about Sascha and Malia being grounded for taking Air Force One for a joyride (extra awkward because it was in reference to recent low altitude Air Force flyover in Manhattan that had everyone more than a little freaked out). It got better when he joked about Dick Cheney writing a book called How to Shoot Friends and Interrogate People, and later called John Boehner "a person of color, although not a ­color that appears in the natural world."


This was the year that Obama learned to go a little harder on his targets. He started by referencing his falling approval ratings: "I am glad that the only person whose ratings fell more than mine last year is here tonight. Great to see you, Jay," he said, addressing Jay Leno, that year's host. "I'm also glad that I'm speaking first, because we've all seen what happens when somebody takes the time slot after Leno's."

The president also got in a few good digs on Scott Brown, Sarah Palin, and Mitt Romney, sprinkled with some more pop culture references we'd rather forget (hello, Jersey Shore).


In 2011, the president tried his hand at more self-deprecating humor. Fresh off the release of his birth certificate to quell xenophobic conspiracy theorists, he opened with his "secret birth video," the scene from The Lion King where Simba is presented to his kingdom. He then addressed the Fox News table: "That was a joke. That was not my real birth video. That was a children’s cartoon; call Disney if you don't believe me. They have the original long-form version."

He later went full-on attack mode on Donald Trump, who, at that point in time, was just a crazy reality show host: "No one is prouder to put this birth certificate matter to rest than The Donald. And 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?" He went on to eviscerate Trump on his "credentials and breadth of experience," saying that making the choice to fire Gary Busey from Celebrity Apprentice was "the kind of decisions that would keep me up at night. Well handled, sir. Well handled."


This year, Obama really hit his stride, first thanking Congress for taking "a break from their exhausting schedule of not passing any laws to be here tonight," and then picking on host Jimmy Kimmel, whom he said was "perfect for the job since most of tonight’s audience is in his key demographic – people who fall asleep during Nightline." The president had learned by this point to make his political jokes a little less "insider," reminding the audience that Kimmel once hosted The Man Show: "In Washington, that’s what we call a congressional hearing on contraception."

The president also made more than one reference to the controversy surrounding the recent news that he'd once eaten dog as a child in Indonesia, and then made some promises for his second term: "In my first term, we ended the war in Iraq; in my second term, I will win the war on Christmas. In my first term, we repealed the policy known as 'don't ask, don't tell;' in my second term, we will replace it with a policy known as 'it's raining men.'" This is what it looks like when someone's got no more elections to win.


Three years after his first joke about the Tonight Show debacle, the president was back at it again, saying that when the WHCA first considered Conan O'Brien to host, "they were faced with that age-old dilemma: Do you offer it to him now, or wait for five years and then give it to Jimmy Fallon?"

He later called out businessman Sheldon Adelson for spending $100 million on negative ads against the Obama. "You’ve got to really dislike me to spend that kind of money. I mean, that’s Oprah money. You could buy an island and call it Nobama for that kind of money." He also referenced Republicans' need to reach out to minorities: "Call me self-centered, but I can think of one minority they could start with. Hello? Think of me as a trial run, you know?"


This year, the president focused more heavily on himself, starting with the botched Healthcare.gov website. "In 2008, my slogan was 'Yes We Can.' In 2013, my slogan was 'Control-Alt-Delete.'"

He also referenced — for the 100th and 101st time — the false allegations that he was born in Kenya: "An American won the Boston Marathon for first time in 30 years, which was inspiring and only fair, since a Kenyan has been president for the last six." And later: "Let’s face it, Fox, you’ll miss me when I’m gone. It will be harder to convince the American people that Hillary was born in Kenya."

He did get in a few good barbs on others, including the infamous zinger, "House Republicans actually give John Boehner a harder time than they give me, which means orange really is the new black."


As the last term grew shorter, Obama's DGAF became more pronounced: "After the midterm elections, my advisors asked me, 'Mr. President, do you have a bucket list?' And I said, 'Well, I have something that rhymes with bucket list.'"

He touched on the issue of same-sex marriage more than once, joking that he and Vice President Joe Biden had "gotten so close, in some places in Indiana, they won’t serve us pizza anymore." In response to Rick Santorum's assertion that he wouldn't attend the same-sex wedding of a friend or a loved one, Obama said, "Gays and lesbians across the country responded, 'That’s not going to be a problem.'"

The finale, of course, was quite possibly the best thing to happen in comedy in 2015: Keegan-Michael Key's appearance as Luther, the president's "anger translator." I refuse to type up even one word, because everyone should watch the skit in full, which begins at 14:20 in the above video. I don't know if it's even possible to top this, but I can't wait to see him try.