The US president, whose administration has often been at odds with the press, started his speech by mostly going along with the warm and relaxed tenor of the evening, alternately mixing friendly jokes with pointed criticism of what he calls the "fake news media".
But he also could not resist taking cracks at his political adversaries in the press and show business, singling out for personal attacks journalists such as Don Lemon and Lawrence O'Donnell, politicians like Chris Christie and Adam Schiff, and celebrities including Bruce Springsteen and Jane Fonda.
Trump suggested he was going easy on the press after he had planned a more fierce criticism last time around.
"This place is really the largest group of Trump Derangement Syndrome people ever put together at one time," he said.
"I suspect some of you are lucky that our last dinner was cut short because … I was going to go after you."
This year's dual events marked Trump's first presidential appearance at the correspondents' dinner. He had boycotted the event during his previous years in office, though he promised to come back in 2027.
Press freedom advocates have criticised the Trump administration over lawsuits it has filed against media organisations, restrictions on some journalists' access, and threats of action against broadcasters. He rejects the criticism, saying his administration is promoting accountability and addressing bias.
The black-tie gathering of journalists, politicians and administration officials at the Washington Hilton hotel was called off on April 25 after a man tried to force his way through a security checkpoint and fired a shotgun outside the ballroom where Trump and members of his cabinet were taking their seats.
The suspect, Cole Allen, pleaded not guilty in May to charges including attempting to assassinate the president.
The dinner was moved to a smaller venue at the Waldorf Astoria hotel under heightened security, and one of the first messages of the night was defiance in the face of the assault.
"Tonight, our message is this: We are back. We will not be intimidated. We refuse to let an act of violence have the final word," said the outgoing president of the White House Correspondents' Association, Weijia Jiang of CBS News.
Trump later said, "We do not yield to political violence ... No deranged loser with a gun will ever change that."
The event also honoured Secret Service officer Victor Gonzales, who was shot at a security checkpoint outside the ballroom in April and is credited with stopping the attack, and the Washington Hilton staff who assisted guests. Gonzales was wearing a protective vest and was the only person wounded that night.
The gala – an annual fixture on Washington's calendar for more than a century – raises money for journalism scholarships and celebrates press freedoms as guaranteed by the First Amendment of the US Constitution.
It normally features a comedian who pokes fun at the president and the press, but this year's entertainment came from mentalist Oz Pearlman.
Trump punctuated his speech with a few jokes, telling journalists, "I know it was not easy finding shoes to go along with your bulletproof vest, which many people didn't want to wear because they'd rather die than look 20 pounds heavier."
