Mr Obama took no prisoners as he targeted the General Services Administration scandal, even the Secret Service and Donald Trump with scattershot humour at the celebrity-studded White House Correspondents' Dinner.
Even the entrance to his speech was part of his comic performance. Mr Obama walked off stage just before he took the podium with an alleged "hot mic," making fun of getting caught last month on an open microphone with Russian President Dmitry Medvedev.
Once on stage, Mr Obama revisited last year's dinner, which took place as Navy SEALS were dispatched to capture and kill Osama bin Laden.
"Last year at this time, this very weekend, we finally delivered justice to one of the world's most notorious individuals," Mr Obama said. Then a picture of real estate mogul Donald Trump appeared on the room's television monitors.
Mr Obama also took a shot at the Republican congressional leadership, thanking them "for taking time from their exhausting schedule of not passing any laws" to attend the dinner.
Four years ago, Mr Obama recalled, he was locked in a tough primary fight with Hillary Clinton, now his Secretary of State. "She can't stop drunk texting me from Cartagena," he said, referring to their recent trip to the Summit of the Americas in Colombia, where Mrs Clinton was photographed drinking a beer and dancing.
This year, Mr Obama is the incumbent, but the dinner was far from a campaign-free zone. He pointed out his similarities with presumed Republican nominee, Mitt Romney.
"We both think of our wives as our better halves, and the American people agree to an insulting extent," Mr Obama said. "We both have degrees from Harvard. I have one, he has two. What a snob."
The crack drew a thumbs up from former Pennsylvania Senator Rick Santorum, who was in the audience. Mr Santorum dropped out of the presidential campaign earlier this month. He had called Mr Obama a snob for encouraging Americans to attend college.
"Never forget that our country depends on you to help protect our freedom, our democracy and our way of life," Mr Obama said.
Then he returned to the lighter side: "I have to get the Secret Service home in time for their new curfew." The Secret Service on Friday announced new conduct rules for its agents to shake the disgrace of a prostitution scandal in Colombia.
Mr Kimmel, the night's featured entertainer, picked up on the Secret Service scandal.
"If this had happened on President Clinton's watch, you can damn well bet those Secret Service agents would have been disciplined with a very serious high five," Mr Kimmel said.
Proceeds from the dinner go towards scholarships for aspiring journalists and awards for distinction in the profession.