Well, that was awkward.

If you’ve ever squirmed through a mean-spirited, ill-advised wedding toast delivered by somebody’s inappropriate, drunk uncle, then you’ll have some sense of the feeling in the room at New York’s Waldorf-Astoria hotel on Thursday night, where Donald Trump and Hillary Clinton attended the annual fundraiser for Catholic charities known as the Al Smith Dinner.

The event has become a regular stop near the end of the presidential campaign cycle over the past decade, but its history stretches back more than 70 years. Over time, nominees have been invited or excluded based largely on their relationships with the Catholic Church. But under the leadership of New York Cardinal Timothy Dolan, a famously gregarious churchman, during the last few elections all have been welcome for a light evening away from the campaign trail, to relax and poke some fun at themselves.

That may change after this year.

Not quite 24 hours after they left the debate stage in Las Vegas, Clinton and Trump sat just a cardinal away from each other on the dais at the Al Smith Dinner, named for the New York governor who was also the first Catholic major party nominee for the White House in 1928. Trump won the coin toss to speak first — if he hadn’t, joked Al Smith IV, he would have cried foul about the “rigged” coin — and quickly made clear that there wasn’t going to be much self-deprecating humor this year.

“A special hello to all of you in this room who have known and loved me for many, many years,” Trump began. “I’d become their best friends. They asked for my endorsement.” But, he continued, since he began running for president, “[They] decided…that I’ve always been a no-good rotten disgusting scoundrel.” It wasn’t a joke. It was Trump’s lifelong bitterness over the ridicule he’s endured from the New York elites who have never accepted him.

With the crowd confused, Trump moved along to a few light jokes aimed at his opponent — “I’m sure Hillary is going to laugh a lot tonight. Maybe even at an appropriate moment.”

Another line got a huge laugh from the crowd, including Clinton herself — “I bumped into Hillary backstage and she said, ‘Pardon me.’” It would have been funnier if he hadn’t threatened to put her in jail during their second debate.

Trump didn’t dabble much in self-deprecating humor, which is traditionally the norm at Al Smith Dinners. He did, however, deliver one jibe at the expense of his wife, admitting that she didn’t know about it in advance — “Michelle [Obama] gives a speech and everyone loves it, it’s fantastic. My wife, Melania, gives the exact same speech and people get on her case.”

And then the evening went off the rails. Dropping the pretense of humor, Trump began lobbing attack lines he uses in his campaign rallies, at one point calling Clinton “so corrupt — so corrupt — she was fired from the Watergate committee.” On the dais behind him, the eyes of dinner guests bulged, and to his left, Clinton, who had been gamely playing along with a broad smile and laugh, froze.

The crowd began booing, an almost unheard-of occurrence at these generally clubby dinners. Jimmy Carter found himself booed when he appeared with Ronald Reagan in 1980, but that was based on policy differences. Conservative Catholics who thought the evangelical Carter would be a fellow abortion opponent when he was elected in 1976 had lost faith in him after four years in the White House and were further angered by his White House conference on families, which they saw as threatening the definition and structure of traditional families.

When Trump brought up WikiLeaks, the boos and hisses increased in volume, and he stopped to acknowledge them. “That’s OK. I don’t know who they’re angry at,” he said, turning to Clinton. “You or I.” From the audience, someone hollered “You!”

Undeterred, Trump continued, saying of Clinton: “Here she is now in public, pretending not to hate Catholics.”

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