No U.S. President has been a better comedian than Barack Obama. It’s really that simple.  
Now that doesn’t mean that some modern-day presidents couldn’t tell a joke. John F. Kennedy, Ronald Reagan, and Bill Clinton excelled at it. But Obama has transformed the way presidents use comedy—not just engaging in self-deprecation or playfully teasing his rivals, but turning his barbed wit on his opponents.
He puts that approach on display every year at the White House Correspondents’ Dinner. This annual tradition, which began in 1921 when 50 journalists (all men) gathered in Washington D.C., has become a showcase for each president’s comedy chops. Some presidents have been bad, some have been good. Obama has been the best. He’s truly the killer comedian in chief.
Presidents typically play it safe at the dinner. You can never go wrong with self-deprecating jokes; they make you more likable. But Obama rejected this approach. Instead, he has used the chance to filet his rivals. It’s like a comedic version of Game of Thrones, but instead of gouging out people’s eyes, Obama kills with punchlines.
And it’s not just the material. Obama has a comedian’s understanding of timing. Last year, I had the chance to tell him so in person. He paused just long enough, and then responded: “I know.”
To appreciate Obama’s performance, it helps to look back at how some of his predecessors have fared at the dinner. In 1988, Ronald Reagan delivered a joke that epitomizes the way past presidents used comedy. The 77-year-old president said that his staff told him “preparing me for a press conference was like reinventing the wheel. Not true. I was around when the wheel was invented, and it was easier.”
Bill Clinton gave us a parade of these types of jokes over the years. For example, in 1994, with his approval ratings dropping, he shared what he jokingly claimed were letters he had recently received offering him support: “Here's one from my pollster, Stan Greenberg: ‘I don't have a clue what people want from you. Trust your instincts, but send the check anyway.’”
And at his final Correspondents’ Dinner in 2000, with the Monica Lewinsky scandal still lurking, Clinton joked, “In just eight years I have given you enough material for 20 years.”  
Then there was George W. Bush, a man who should be in the comedy hall of fame for all the material he gave comedians. Bush seemed to relish in telling jokes at his own expense, even poking fun at his struggle to pronounce multisyllabic words. At the 2005 Correspondents’ Dinner he opened by saying, “I look forward to these dinners where I’m supposed to be funny...intentionally.”
So into this kinder, gentler world of presidential comedy stepped Obama. His preferred jokes were of the type made popular by Jon Stewart on The Daily Show. Obama’s comedy, like that of Stewart, HBO’s John Oliver, and the Comedy Central host Larry Wilmore—who is hosting this year’s Correspondents’ Dinner—has a bite to it. In fact, Obama’s jokes have been criticized as “caustic” or “cruel.”
Over the years Obama has slammed everyone from his GOP rivals to billionaires like Sheldon Adelson to actors like Matt Damon who once supported him but then publicly turned on him. One of my favorite Obama jokes came in 2013 when he brought the house down with this biting line: “Some folks still don’t think I spend enough time with Congress. ‘Why don’t you get a drink with Mitch McConnell?’ they ask. Really? Why don’t you get a drink with Mitch McConnell?!”
In 2014 Obama went after the media, but not playfully like past presidents. He cut to the bone with jokes like this: “MSNBC is here. They’re a little overwhelmed. They’ve never seen an audience this big before.” He then pivoted to take on his media nemesis on the right: “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.”
And in 2015 Obama really let loose—hitting everyone from Dick Cheney to Ted Cruz to Benjamin Netanyahu. One of the jokes that stands out as something you never would’ve heard a past president tell was his needling of John Boehner for unilaterally inviting Netanyahu to address Congress: “People keep pointing out how the presidency has aged me. I look so old John Boehner’s already invited Benjamin Netanyahu to speak at my funeral.”
Obama then moved on to the 2016 presidential race, taking on Ted Cruz, who had a short time before compared himself to Galileo: “Galileo believed the Earth revolves around the sun. Ted Cruz believes the Earth revolves around Ted Cruz”
Now, other presidents have taken isolated shots at rivals at the Correspondents’ Dinner. And Obama has mixed self-deprecating material in among his barbs. But no one before has used comedy as a weapon to prod and taunt his rivals to the same extent as Obama.
So what will Obama offer at his final Correspondents’ Dinner on Saturday night? I’d predict a parade of jokes mocking the 2016 Republican presidential field and especially one Donald J. Trump. Back in 2011, when Trump was considering running for president and sitting in the audience, Obama ripped into him—not just with one joke but with a series of barbs mocking Trump on various issues from his flashy style to his fixation with Obama’s birth certificate.
The best of the lot, which remains relevant today, ridiculed Trump for his lack of experience to serve as commander in chief: “We all know about your credentials and breadth of experience. For an episode of Celebrity Apprentice... the men’s cooking team cooking did not impress the judges...And there was a lot of blame to go around. But you, Mr. Trump, recognized that the real problem was a lack of leadership. And so ultimately, you didn’t blame Lil’ Jon or Meatloaf. You fired Gary Busey. And these are the kind of decisions that would keep me up at night.”
Saturday night will be a bittersweet Correspondents’ Dinner. Sure, there will be laughs. But for fans of political comedy, there will be a sense of loss, as a killer comedian in chief exits the stage.