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There was the time Ellen DeGeneres, just days out of the closet, canoodled with new girlfriend Anne Heche right in front of Bill Clinton. The time George W. Bush goofed around with a George W. Bush impersonator. The time Barack Obama dunked on reality TV star Donald Trump to the rapturous shrieks of media elite.

What a time to be alive, and in attendance, at the White House Correspondents’ Association dinner!

An event by that name is happening again this weekend. Many Washingtonians with entree to media-political circles will armor themselves in black tie or sequins in hopes of snuggling up to a “Vanderpump Rules” star for a selfie, and many more will surely gather the family around C-SPAN Saturday night to chortle over the comedy stylings of the current commander in chief and a guy from “The Daily Show.”

But if any of those people think they’re witnessing the White House correspondents’ dinner — sorry, you already missed it. The pageantry is all just a pantomime at this point, a costumed reenactment paying homage to a golden age of Beltway excess and aspiration, defined by an unbroken quarter-century succession of (we’re just going to come out and say it) cute presidents. Clinton. Bush. Obama.

Love them or hate them, it cannot be denied that this was a unique era in both Washington and popular culture, when the nation happened to be led by suave, quippy young boomers with low resting heart rates and fully intact natural hairlines, and who all looked great in a tux. And that era produced some pretty memorable parties.

Was the dinner bad for America? Did it amplify Washington’s worst impulses — the chumminess, the insular tone-deafness, the willingness to let lobbyists pick up the tab? Perhaps! But for a while, it certainly gave us something to talk about.

May 1, 1993: Washington was emerging from a recession and a brutal winter, and on this night it was graced by something like royalty: the Honorable Barbra Streisand, EGOT. Fresh from financing the Democratic victories of the previous fall, she swanned through the shadowy expanses of the Washington Hilton ballroom as if key-lit from within, a vision in off-the-shoulder cream, pearls and diamonds — and the town’s media heavyweights just about lost their damn minds.

Greg Gibson

“I’ve been a great fan of yours all my life,” CNN’s Wolf Blitzer informed the ambassador from Malibu, prying her away from Gen. Colin Powell, with whom she had been conferring about gays in the military. Even loquacious professional cynic Christopher Hitchens, who in those days hosted a boozy cool-kids after-party at his Kalorama condo, was left dumbstruck.

“I ended up saying, ‘I loved you in ‘The Way We Were,’” Hitchens confided to a reporter later that night. “I was so embarrassed.”

C-SPAN had decided to broadcast the spectacle for the first time and got way more than it bargained for. Blame or credit Elayne Boosler, the night’s hired entertainer. Sliding into a gig traditionally worked by prime-time friendlies like Rich Little or Dick Cavett, the ’70s nightclub veteran dutifully dabbled in political humor before settling into her wheelhouse: sex.

“This is the man you want in charge of the bombs!” she exclaimed about the late Sen. John Tower, only two years dead at the time, whose hard-partying reputation had scuttled his shot at running the Pentagon. “A guy who wants to live! He’s smoking, he’s drinking, he’s trying to get laid. He just wants to make it to another Saturday night!” (Trust us: This was wild material, for that room, for that moment.)

But she was merely the opener for our pink-cheeked new prom king, William Jefferson Clinton, who chuckled and aw-shucksed his way through a riff about his first-100-days travails.

“I’m not doing so bad,” he rasped. “I mean, at this point in his administration, William Henry Harrison had been dead 68 days!”

Pablo Martinez Monsivais

The correspondents’ dinner predated the Clinton-Bush-Obama years, of course. But for seven decades, it had served simply as an annual hail-fellow-well-met interlude between Washington’s press corps and the people it covered — not just the chief executive, but also the lower-level officials and politicians who made and implemented policy.

It was a low-key, inside-the-Beltway night, pleasant but unremarkable. Bob Hope sometimes hosted. Female correspondents weren’t invited until the early 1960s.

Faint hints of disruption came in the waning years of the Reagan era. In 1987, Baltimore Sun reporter Michael Kelly famously threw a curve into the invite-a-newsmaker tradition by bringing Fawn Hall, the beautiful blond secretary at the center of the Iran-contra scandal. A year later, he jolted the room again by escorting Donna Rice, the Other Woman who sank Gary Hart’s presidential hopes.

I sat next to Donald Trump at the infamous 2011 White House correspondents’ dinner

But the celebrity explosion began with Clinton, the first boomer president, who had an innate understanding of pop culture. He had braved the cringe to toodle a saxophone on “The Arsenio Hall Show.” The hit-making producers of the sitcom “Designing Women” crafted his swooning biographical film for the campaign; Fleetwood Mac, only a few years removed from their chart-topping days, reunited to play his inauguration. So, yeah, you can imagine what those dinners were like.

“Clinton loved anything that was fun,” said Ann Stock, a former White House social secretary. “And it was a fun night.”

It was a fun time in general. Washington was beginning to enjoy an influx of money and cachet. Fourteenth Street, the city’s erstwhile red-light district, begin to fill up with fashionable restaurants. No one was jaded about any of this, not yet. When the dinner rolled around, crowds of autograph seekers formed outside the Hilton, and the competition for the limited number of tickets surged.

Doug Mills

The intersection of traditional Washington and Hollywood Washington was irresistible: After Michael Douglas starred in 1995’s “An American President,” he was greeted as something like the doppelganger in chief whenever he showed up for the White House correspondents’ dinner weekend. By the time “The West Wing” debuted on NBC in 1999, the real White House and its fictional double had been melded into a fast-talking, liberal fever dream. The 2000 dinner opened with <a href="https://www.youtube.com/watch?v=hLBs1IdzQjs" target=_blank>a seven-minute video</a> starring the TV cast and the real White House press secretary, Joe Lockhart.

“The White House correspondents’ dinner is meant to honor serious journalists,” Lockhart told his fictional counterpart, actress Allison Janney, in the clip. “A lot of people are really uncomfortable with the Hollywood-izing of government.”

Big laugh. All the cast members were at the dinner, of course, and treated as if they were actual administration officials. Weird, yes, but “shows like ‘West Wing’ became a civics course in why government matters,” said Melissa Moss, a former finance director of the Democratic National Committee. And that was intoxicatingly flattering for a town like Washington.

The Hollywood ardor cooled a little with the advent, in 2001, of a Republican administration. But by then, the dinner was taking on its own momentum — and a whole new class of entertainment celebrities had emerged. They were reality TV stars — from “Survivor,” from “American Idol” — happy to fill Streisand’s empty seat if offered, and yet they were no less mesmerizing to their Washington banquet partners, at least during their moment of white-hotness.

Even the new Republican president was willing to play ball.

In 2002, Greta Van Susteren — at the time a hard-edge Fox News host who turned out to have extremely playful tastes in White House correspondents’ dinner guests — brought Ozzy Osbourne and his wife, Sharon, at the height of their new fame as MTV reality stars. Ozzy, the perpetually dazed heavy-metal pioneer, flung himself into the spirit of things, making his way to the front of the room, where Bush was seated at the head table.

Stefan Zaklin

The two men gazed at each other across the Secret Service’s 10-foot DMZ, reported our colleague David Montgomery. Ozzy made a prayerful gesture. Bush nodded.

And then Ozzy grabbed a hank of his shoulder-length brown-and-pink hair and shouted:

The president paused, flushed momentarily, then grinned.

“Second term, Ozzy!” he shouted back.

What started with cocktail receptions hosted by news organization exploded into a marathon of events piggybacking on the dinner. People magazine handed out groaning gift bags, but the undisputed A-list bash was Vanity Fair’s, sometimes in partnership with Bloomberg — elegantly over the top, filled with stars, and almost impossible to crash. If you could get in, though, it could beguilingly intimate. It was the place to see John F. Kennedy Jr. tenderly cuddling his wife, Carolyn Bessette-Kennedy — captured in an <a href="https://www.washingtonpost.com/lifestyle/style/jfk-jr-and-carolyn-showed-us-how-to-be-famous-for-being-famous--before-discretion-became-obsolete/2019/07/15/c468f1c0-a706-11e9-86dd-d7f0e60391e9_story.html" target="_blank">enduringly romantic photo</a> that broke hearts after they were both killed in a plane crash months later.

“In the years before social media, when you had these cultural icons in town, there was a novelty and singular thrill of being in the room,” said Juleanna Glover, a veteran public-affairs consultant.

Tyler Mallory

The excitement over the election of the first Black president sent the correspondents’ dinner into overdrive, the parties becoming a glut of A-listers: Demi and Ashton, and Affleck and Garner, and Kim Kardashian, and the Jonas Brothers, and Justin Bieber, strutting around as if he owned the joint. The dinner became an important stop on the promotional junket for any show or movie about politics — “Homeland” star Claire Danes, “Scandal” star Kerry Washington, “House of Cards” star Kevin Spacey, who brought down the house with his <a href="https://www.youtube.com/watch?v=dCzI521sgqE" target=_blank>“House of Nerds” spoof video</a> in 2013. (Co-starring presidential adviser Valerie Jarrett, Sen. John McCain, Rep. Kevin McCarthy, Mike Bloomberg and a number of Washington reporters.)

“Washington and Hollywood,” intoned Spacey’s Frank Underwood. “Some new faces, some old faces, some new faces on old faces.”

Obama rose to the occasion, one year tag teaming with rising comedic powerhouse Keegan-Michael Key, who played <a href="https://www.washingtonpost.com/news/reliable-source/wp/2015/04/26/how-barack-obama-and-his-anger-translator-finally-got-on-stage-together/" target=_blank>Luther, the president’s “anger translator,”</a> voicing the supposed rage simmering beneath Obama’s cool demeanor.

Obama: “Despite our differences, we count on the press to shed light on the most important issues in our day ...”

Luther: “We count on Fox News to terrify old white people with some nonsense! ‘Sharia law is coming to Cleveland, run for the damn hills!’ Y’all ridiculous!”

Olivier Douliery

And then what happened? Well, Trump happened.

If you were the kind of person who hated Trump <i>and</i> hated the White House correspondents’ dinner, you might have blamed the latter for the former — going back to the night in 2011, when both Obama and comedian Seth Meyers mocked Trump to his face in an electrifying pair of monologues excoriating him for his birther conspiracy theories. … and, supposedly, inspiring him to regroup and run for president.

So what would it be like if Trump came to the dinner as president? We never got to find out. He declined all invitations, but the celebrities and the party hosts had pulled out anyway. The White House Correspondents’ Association struggled to find the right tone, balancing edgy comics with somber lectures on journalism and democracy by the likes of Ron Chernow and Woodward and Bernstein.

Then came the pandemic and two years of no dinner. Some greeted <a href="https://www.washingtonpost.com/lifestyle/2022/05/01/white-house-correspondents-dinner-parties/" target=_blank>last year’s first Biden-era dinner like a cathartic high school reunion</a>, so glad were they to hit the cocktail circuit again … and then woke up the next week with a sore throat and fever.

<a href="https://www.washingtonpost.com/arts-entertainment/2022/04/30/biden-white-house-correspondents-dinner/" target=_blank>President Biden’s speech</a> — well, it was fine, right? Everyone loves old Uncle Joe. Safe, decent, comfortable. No one died of horror. <a href="https://www.washingtonpost.com/arts-entertainment/2022/04/30/trevor-noah-white-house-correspondents-dinner/" target=_blank>Trevor Noah did a routine</a>, and he was probably good? We’ll have to look it up on YouTube.

As for this year, there’s always a chance something will surprise or delight us. But we’re not holding our breath.

There She Was: The Secret History of Miss America

The University of Virginia, B.A. in Political and Social Thought

Amy Argetsinger, an editor for the Style section, joined The Washington Post in 1995. She is the author of "There She Was: The Secret History of Miss America" (2021). She previously served as Reliable Source columnist, Los Angeles bureau chief and a Metro reporter covering higher education and the Maryland suburbs.

Amy Argetsinger

Roxanne Roberts is a reporter covering Washington's social, political and philanthropic power brokers. She has been at The Washington Post since 1988, working for the Style section as a feature writer and columnist.

Roxanne Roberts