First held in 1921, the White House Correspondents’ Association dinner is a Washington institution, loved and loathed by generations of Washington insiders, critics and observers.

Officially a celebration of press freedom and the First Amendment, it is held in a city of rotating administrations and institutions, and it has carried on amid world wars, domestic crises, attempted assassinations and political upheaval. Women correspondents were first invited to attend in 1962.

For more than 50 years, the black-tie event for hundreds of the nation’s most prominent journalists and top administration officials has been held at the Washington Hilton, a sweeping hotel complex in the city’s bustling northwest. It traditionally takes place on the last Saturday in April.

Colloquially nicknamed the “nerd prom,” the annual dinner is celebrated by its defenders as a bipartisan, bread-breaking capacity in a city of sharp knives and sharper elbows, and by the Washington press corps for its role as a fund-raiser for journalism scholarships. But to critics, the event has long stood as an example of the coziness between the country’s power brokers and those who report on them, as well as celebrities and Hollywood stars.

Still, the dinner has taken place against the backdrop of history. In 1942, the dinner was canceled as the country entered World War II. In 1981, then-President Ronald Regan did not attend as he was recuperating after surviving an assassination attempt, which occurred weeks earlier outside the same hotel in which the dinner was being hosted. In 2006, in the midst of the Iraq and Afghanistan Wars, Stephen Colbert skewered the Bush administration so sharply during a nearly 20-minute address that several administration officials walked out.

The event has taken on a new pallor in the age of the Trump administration, which has repeatedly attacked the news media and members of the press.

This was the first year that Mr. Trump had attended the event as a president, having eschewed the invitation during his first term. Before this year’s event, hundreds of journalists signed an open letter asking the White House Correspondents’ Association to forcefully protest Mr. Trump’s appearance, given his assaults against the free press.