White House Correspondents’ Dinners past: Kim Kardashian, our favorite guest, and Donald Trump’s hair

David Chalian
Yahoo! News, Washington Bureau Chief

Every year I find myself wondering why Hollywood celebrities would want to fly east to sit in a cavernous hotel ballroom in a town famous for its lack of style. But then I find myself in conversations with random celebrities, many of whom are clearly extremely interested in specific issues and in the overall political landscape.

The most surprising conversation I had at a dinner was a few years back when I was introduced to Kim Kardashian and she became intrigued by my last name's Armenian heritage. She began to educate me about the Armenian genocide well beyond anything I had ever known prior to meeting the Hollywood starlet. It was a good thing she steered the conversation and informed me all about this issue near and dear to her because I had never seen her reality TV show and didn't know what we would talk about. Who woulda thunk?

Jake Tapper
ABC News Senior White House Correspondent

In 2005, my "date" for the dinner was then-"Daily Show" correspondent Stephen Colbert; the previous year I kept running into him on the campaign trail in the most random spots (chasing down Howard Dean backstage at Carroll High School in Iowa, in the hallways of the history department at the University of South Carolina).

During the dinner, Colbert excused himself and was gone for a bit. When he returned he told me he had been on the phone with his agent, and they had just finalized the deal for his own show. It was a great moment for him, and fun to be able to revel in his success, but I must confess I wondered to myself if he would be able to maintain the Colbert "character" for a full half-hour. Shows you how much I (don't) know about comedy; his show took off and he was the performing comedian at the next year's dinner.

Martha Raddatz
ABC News Senior Foreign Affairs Correspondent

I love who ends up becoming your photographer at these events. The year quarterback Tom Brady was at my table, people were climbing over Colin Powell to get to him. And several of the young women who were flocking to the table asked Gen. Powell if he would take their picture with Tom Brady.

I have had a few "four-stars" as my official photographer as well. This picture from 2008's dinner is Gen. Peter Chiarelli taking a picture of me with Morgan Fairchild.

Jonathan Karl
ABC News Senior Political Correspondent

For me, one of the most memorable WHCD moments was when Ozzy Osbourne stole the show during the 2002 dinner, jumping out of his seat and raising his arms to thunderous applause when Bush mentioned his name. Bush read through the names of some of Ozzy's hits—"Sabbath Bloody Sabbath," "Bloodbath in Paradise," etc.—and said, "Ozzy, Mom loves your stuff." Classic.

Ann Compton
ABC News Radio, National Correspondent

I was seated next to the lectern at the head table in 2007 when Bush 43's stunt double, Steve Bridges, came onstage as a total surprise to join the president for his routine.

Rick Klein
"World News With Diane Sawyer," Washington Editor

The dinner's red carpet is about the oddest mix of celebrity and politics you can imagine—Eric Cantor and Alec Baldwin, Kim Kardashian and Scott Brown, jockeying for the cameras. And when the two worlds intersect, it's gold.

Last year, Marlon Wayans caught a glimpse of Donald Trump—the IT guest of the year, since he'd just succeeded in getting President Obama to reveal his birth certificate. Wayans mused aloud that he should give Trump's hair a healthy tug—a comedic moment, alas, that never came to be. But it's even better when a pol plays the celebrity game himself. In 2010, then-RNC Chairman Michael Steele was glowing by the time he reached the red carpet, raving about having just caught up with his "buddy" Chris Tucker. Tucker was less impressed: "Who is Michael Steele?"

Sara Just
ABC News Digital, Senior Washington Editor

My favorite moments at the White House Correspondents' Dinner are the unlikely combinations of people you see in one place—often talking to each other. I will never forget walking past Supreme Court Justice Antonin Scalia at an after-party one year while he was having what looked like an in-depth conversation with Pamela Anderson. You don't see that every day.

Olivier Knox
Yahoo! News, White House Correspondent

My favorite moment from the White House Correspondents' Dinner came in 2006, when one of my guests was a dear friend—a U.S. Army officer who had just spent 15 months in Iraq. Comic Stephen Colbert riffed at one point on the recent spate of criticisms that retired generals had leveled at then-Secretary of Defense Donald Rumsfeld. "I've got a theory about how to handle these retired generals causing all this trouble," Colbert declared. "Don't let 'em retire!"

I can still hear my friend's rumbling belly-laugh—it was contagious.