In its early years, the dinner featured a mix of singers, dancers and comedians as performers; not until 1983 when Mark Russell headlined did the practice of having a comedian host the event become the norm.
Since then, the Dinner has become a springboard for politically inclined comics to showcase their best material. Here are our five faves. Good luck to this year's host Joel McHale: He's got some big shoes to fill.
5. Wanda Sykes, 2009
Wanda Sykes was the first black woman and the first openly gay person to emcee the Dinner, but anyone who thought she'd be deferential in light of the honor was mistaken. One of her best lines took aim at Obama's then-viral shirtless pics: "I know you're into this 'transparency' thing, but, uh, I don't need to see your nipples. Is there a beach at Camp David? You know, there was never a nipple portrait of Lincoln."
4. Conan O'Brien, 2013
"Fox is the jocks. MSNBC is the nerds. Bloggers are the goths. NPR is the table for kids with peanut allergies. Al Jazeera is the weird foreign exchange student nobody talks to. Print media, you're the poor kid who died sophomore year in a car crash. Cheer up, we dedicate the yearbook to you!"
3. Jon Stewart, 1997
Stewart (whose appearance begins at 42:50 in the clip above) wasn't even the host of The Daily Show yet when he appeared at the Dinner. (Side note: LOOK AT HOW YOUNG HE IS.) "Ellen DeGeneres is here, a very big celebrity. I commend her courage in coming out with her sexuality at much personal risk, I might add," Stewart joked. "Although I still believe it's an elaborate ruse to keep Larry King from hitting on her."
2. Cedric the Entertainer, 2005
"I love that name, Condoleezza. It's so soulful. You know, she's very professional, but Condoleezza – come on, right there. Condoleezza. It's two people, though ... There's the Condi, who's – that's the person you see on television with, you know, the nice hair and very professional. Then there's the Leezza ... She the one with her hair wrapped up on the phone with her girlfriend watching BET, talking about ... 'Girl! Ain't that a surprise? Look at that.'"
1. Stephen Colbert, 2006
Easily the boldest Correspondents' Dinner speech by a mile, Colbert's roast of George W. Bush caused many Bush faithfuls to walk out of the dinner. And it is hilarious.
"I stand by this man. I stand by this man, because he stands for things. Not only for things, he stands on things, things like aircraft carriers and rubble and recently flooded city squares. And that sends a strong message, that no matter what happens to America, she will always rebound with the most powerfully staged photo ops in the world."