President Obama speaks at the annual White House Correspondent's Association Gala at the Washington Hilton hotel May 3, 2014 in Washington, DC.
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May 4, 2014 9:39 AM EDT

Good comedy almost always hurts a little. The trick, of course, is finding the invisible line between the offensive and the hilarious, the vicious and the surprising. This is why Washington, a town built on calculation and caution, is not very funny. People don’t want to take the chance. The risk is too high, and besides, we are not funny.

But there is a regular exception. Once a year, in the ballroom of the Washington Hilton, the President of the United States roasts his enemies and himself, and a name brand comedian from the hinterlands gets a half hour to mock the media, the President and his colleagues before all concerned. Sometimes, the humor is soft (Jay Leno in 2010) and sometimes it is explosive (Stephen Colbert in 2006). On Saturday night, at the 2014 White House Correspondents Association dinner, the jokes tended towards insult comedy, in the best sense.

Neither President Barack Obama nor the comedic host Joel McHale pulled their punches. Obama called two Fox News hosts potted plants, McHale repeated Chris Christie fat jokes and one gibe suggested that George Clooney lives in the colon of the Commander-in-Chief. And that was just the beginning.

So for those readers who had something better to do last night than watch C-SPAN, and that should be pretty much all of you, here is a quick, roughly ranked guide to the 17 meanest jokes of the night.

17. BARACK OBAMA: I want to thank the White House Correspondents Association for hosting us here tonight. I am happy to be here, even though I am a little jet-lagged from my trip to Malaysia. The lengths we have to go to get CNN coverage these days. I think they’re still searching for their table.

16. JOEL McHALE: Thanks to Obamacare, or as the president refers to it, “me-care,” millions of newly insured young Americans can visit the doctor’s office and see what a print magazine actually looks like.

15. OBAMA: MSNBC is here. They’re a little overwhelmed. They’ve never seen an audience this big before.

14. McHALE: Legendary actor Robert De Niro is here tonight, everyone. Now, I don’t do a De Niro impression, but I do an impression of Robert De Niro’s agent. Ready? Here it is. “Ring ring – he’ll do it!”

13. McHALE: Biz Stone, the founder of Twitter, is here. So if any of you congressmen want to cut out the middleman, just show him your penis.

12. OBAMA: Just yesterday, I read a heartbreaking letter — you know I get letters from folks from around the country; every day I get 10 that I read — this one got to me. A Virginia man who’s been stuck in the same part-time job for years; no respect from his boss; no chance to get ahead. I really wish Eric Cantor would stop writing me. You can just pick up the phone, Eric.

11. OBAMA: And I’m feeling sorry — believe it or not — for the Speaker of the House, as well. These days, the House Republicans actually give John Boehner a harder time than they give me, which means orange really is the new black.

10. OBAMA: How well does Obamacare have to work before you don’t want to repeal it? What if everybody’s cholesterol drops to 120? What if your yearly checkup came with tickets to a Clippers game? Not the old, Donald Sterling Clippers — the new Oprah Clippers. Would that be good enough? What if they gave Mitch McConnell a pulse? What is it going to take?

9. McHALE: Between Rob Ford, Justin Bieber and Ted Cruz, you just want to tell Canada, “Hey, hey, relax – we already have a Florida.”

8. McHALE: Every year the White House doctor checks the president’s colon for polyps and George Clooney’ s head. Yeah.

7. McHALE: I am a big fan of that lesbian on MSNBC – Chris Hayes, he’s great.

6. McHALE: House of Cards has had a huge impact on Washington. What a great show. I haven’t seen a Southern senator give a tour de force performance like that since Lindsey Graham played Blanche DuBois in “A Streetcar Named Desire.” And Lindsey, if you’re here now, you can drop character any time, man.

5. McHALE: All right, look, I know it’s been a long night, but I promise that tonight will be both amusing and over quickly, just like Chris Christie’ s presidential bid. I got a lot of these tonight, so buckle up, Governor Christie. Excuse me, extender buckle up.

4. OBAMA: Look, everybody is trying to keep up with this incredibly fast-changing media landscape. For example, I got a lot of grief on cable news for promoting Obamacare to young people on Between Two Ferns. But that’s what young people like to watch. And to be fair, I am not the first person on television between two potted plants. (Shows slide)

3. McHALE: Hillary’s daughter Chelsea is pregnant which means in nine months we will officially have a sequel to Bad Grandpa. It also raises the question, when the baby is born do you give Bill Clinton a cigar?

2. McHALE: I also host a show called The Soup, which is on the E! network, thank you. To Republicans in attendance, E! is the channel that your deeply closeted gay son likes to watch. Democrats, it’s the same channel that your happy, openly gay son likes to watch. E! is also home to the Kardashians, who believe it or not, are Republicans. And I know that because they are always trying to screw black people.

1. McHALE: There’s a lot of celebrities here tonight; they’re the ones that don’t look like ghouls.

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