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.”