Even the entrance to his speech was part of his schtick. The President walked off the stage just before he took the podium with an alleged "hot mic," making fun of getting caught last month on an open microphone with the Russian President Dmitry Medvedev.
"What am I doing here," he asks off stage. "I'm opening for Jimmy Kimmel and telling knock-knock jokes to Kim Kardashian."
Once on stage, the President revisited last year's dinner, which took place as Navy SEALs were dispatched to capture and kill Al Qaeda leader Osama bin Laden.
"Last year at this time, this very weekend, we finally delivered justice to one of the world's most notorious individuals," President Obama said. Then a picture of real estate mogul Donald Trump appeared on the room's television monitors. The President last year delivered a scathing roast of Mr Trump, who flirted with running for the Republican nomination and claimed he had solved the "mystery" of Mr Obama's birth certificate.
The President also took a shot at the Republican congressional leadership, whom he thanked "for taking time from their exhausting schedule of not passing any laws" to attend the dinner.
Four years ago, 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 Columbia.
This year, President Obama is the incumbent, but the dinner was far from a campaign-free zone. The President pointed out his similarities with the presumed Republican nominee, Mitt Romney.
"We both think of our wives as our better halves, and the American people agree to an insulting extent," the President said.
"We both have degrees from Harvard. I have one, he has two. What a snob."
The crack drew a thumbs up from the former Pennsylvania Senator Rick Santorum, who was in the audience. Mr Santorum dropped out of the presidential primary campaign earlier this month. He had called Mr Obama a snob for encouraging young Americans to attend college.
But President Obama touched on serious themes as well, remembering The New York Times' Anthony Shadid and Marie Colvin of the Sunday Times of London who died while covering the uprising in Syria.
"Never forget that our country depends on you to help protect our freedom, our democracy and our way of life," he said.
Then he returned to the lighter side: "I have to get the Secret Service home in time for their new curfew."
Mr Kimmel, the night's featured entertainer, picked up on the Secret Service prostitution scandal in Columbia, saying he told the Secret Service that for $800 he wouldn't joke about them, "but they only offered 30."
"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," he said.
Mr Kimmel later asked President Obama: "You remember when the country rallied around you in hopes of a better tomorrow? That was hilarious."
"There's a term for guys like President Obama," Mr Kimmel said with a pause. "Probably not two terms."
Among the eclectic crowd attending the Saturday night's dinner were former Secretary of State Colin Powell, the cast of the hit TV show "Modern Family," actress Lindsey Lohan, Army Chief of Staff Genereal Ray Odierno, House Majority Leader Eric Cantor, R-Virginia, actor George Clooney and director Steven Spielberg.
Proceeds from the dinner go toward scholarships for aspiring journalists and awards for distinction in the profession.
The association was formed in 1914 as a liaison between the press and the President. Every President since Calvin Coolidge has attended the dinner. Some of the proceeds from the dinner pay for journalism scholarships for college students.
Several journalists were also honored at the dinner:
Matt Apuzzo, Adam Goldman, Eileen Sullivan and Chris Hawley of The Associated Press, for winning the Edgar Alan Poe Award for their stories about the New York City Police Department's widespread surveillance of Muslims after the September 11 terror attacks. It's the fourth major prize for the series, which has also won the Pulitzer Prize for Investigative Reporting, the Goldsmith Prize for Investigative Reporting and a George Polk Award.
ABC's Jake Tapper and Politico's Glenn Thrush, Carrie Budoff Brown, Manu Raju and John Bresnahan, for winning the Merriman Smith Award for excellence in presidential coverage under pressure. Tapper won in the broadcast category for breaking the news that rating agency Standard & Poor's was on the verge of downgrading the federal government's triple-A credit rating because of concerns over political gridlock in Washington. In the print category, Thrush, Budoff Brown, Raju and Bresnahan of Politico won for their report on the deal between Obama and congressional Republicans to raise the US debt ceiling.
Scott Wilson, of The Washington Post, for winning the Aldo Beckman award. Wilson was recognized for his "deeply reported and nuanced stories, his evocative writing and his clear presentation of complex issues, particularly on the foreign policy front."
Video courtesy: YouTube