The Washington Press Corps at Work and at Play: Classic Photos

Each year, much of the mainstream media manages to work itself into a self-congratulatory lather around the time of the annual White House Correspondents’ Dinner — and, of course, the event’s attendant parties, meet-and-greets and other (largely booze-fueled) functions. That said, not everyone is besotted with the spectacle.

Some notable outfits, like the New York Times, don’t attend the dinner, evidently finding the cheek-by-jowl mix of celebrities, journalists, politicians and other characters rather smarmy — or, as one Times editor reportedly put it: “The press and pols take their costumes off, sing together, mingle with celebrities and act like we are all in it together.”

An unsettling image, no matter how literally one chooses to take it.

But even those who view the proceedings with a decidedly jaundiced or gimlet eye can, perhaps, appreciate the spirit in which the dinner takes place. After all, one can hardly expect White House correspondents to constantly, perpetually inhabit their dogged, adversarial reporting roles. Right? And besides, now that the correspondents’ dinner has become a kind of South by Southwest for wonks, with celebrities and tech upstarts on hand all weekend to lend the affair a gloss of sex and relevancy, who can really hold it against the pols and the press if, for one night a year, they feel like — in the words of our anonymous friend at the Times — taking off their costumes and singing?

Here, in tribute to the intrepid men and women who cover the White House, and Washington in general, LIFE.com presents a series of photos from the last century — pictures of reporters, correspondents, photographers and newscasters who, with their pens, cameras, typewriters and microphones, tried to make sense of the riddle wrapped in a mystery inside an enigma that is the modern American political landscape.