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Trump and Clinton just roasted each other at a charity dinner, and boy was it awkward

Andrew Prokop is a senior politics correspondent at Vox, covering the White House, elections, and political scandals and investigations. He’s worked at Vox since the site’s launch in 2014, and before that, he worked as a research assistant at the New Yorker’s Washington, DC, bureau.

On Thursday night, both Hillary Clinton and Donald Trump spoke at the Alfred E. Smith Memorial Foundation Dinner in New York City. It’s an annual charity event with high-powered political and media figures that’s usually lighthearted and fun — weeks before the last presidential election, Mitt Romney and Barack Obama put in funny, self-deprecating performances there.

This … was not that.

Donald Trump spoke first, and his speech was deeply strange.

He began with a riff that, delivered properly, could have come off as lighthearted — but, with his actual delivery, sounded embittered and angry.

TRUMP: And a special hello to all of you in this room who have known and loved me for many, many years — the politicians.

They have had me to their homes. They have introduced me to their children. I have become their best friends in many instances. They have asked for my endorsements and they always wanted my money.

They even called me, really, a dear, dear friend — but then suddenly decided when I ran for president as a Republican, [voice rises] that I’ve always been a no-good, rotten disgusting scoundrel! And then totally forgot about me.

Trump went on to make some slight movements in the direction of self-deprecating jokes, while never quite landing one — though he did manage to deliver a good joke about his wife Melania’s plagiarized convention speech, prefacing it by saying, “This one is going to get me in trouble”:

TRUMP: You know, the president told me to stop whining, but I really have to say, the media is even more biased this year than ever before. You want the proof? Michelle Obama gives a speech, and everyone loves it. It's fantastic. They think she is absolutely great. My wife, Melania, gives the exact same speech — and people get on her case! And I don't get — and I don't get it. I don't know why.

But eventually, he started saying things that were barely even jokes, but were mainly attack lines from his campaign:

TRUMP: Hillary is so corrupt, she got kicked off the Watergate Commission. How corrupt do you have to be to get kicked off the Watergate Commission? [booing] Pretty corrupt. [Note: This is not true.]

Hillary is and has been in politics since the 1970s. What is her pitch? The economy is busted, the government is corrupt, Washington is failing. Vote for me. I have been working on these problems for 30 years. I can fix it, she says.

Further “jokes” included:

  • “Hillary Clinton believes it is vital to deceive the people by having one public policy [boos] and a different policy in private … Here she is tonight in public, pretending not to hate Catholics.”
  • “Everyone knows, of course, Hillary has believed that it takes a village, which only makes sense, after all, in places like Haiti, where she has taken a number of them.” [boos]
  • “Hillary has been in Washington a long time. She knows a lot about how government works. And according to her sworn testimony, Hillary has forgotten more things than most of us will ever, ever know, that I can tell you.” [boos]

Here’s an example of the reaction from one attendee:

Clinton went up right after Trump and delivered a speech that — while more self-deprecating and better-delivered than the GOP nominee’s — did take potshot after potshot at him.

She repeatedly joked about Trump’s talk of a “rigged” election, saying, for instance, “Come to think of it, it's amazing I’m appearing after Donald. I did not think he would be okay with a peaceful transition of power.”

And she took shots at his sexism:

  • “People look at the Statue of Liberty and see a proud symbol of our history as a nation of immigrants, a beacon of hope for people around the world. Donald looks at the Statue of Liberty and sees a 4. Maybe a 5 if she loses the torch and tablet and changes her hair.”
  • “Donald has attacked me for a life in public service. I did not get that at first. I kind of get it now. As he told Howard Stern, he does not like it when women have been around for more than 35 years.”

Overall, the crowd seemed uneasy with both performances, and it was clear that there was no love lost between the two candidates in this very nasty election year. When Clinton mentioned how it had been a “long, long campaign,” viewers likely agreed and yearned for its promised end.