Donald Trump and Hillary Clinton have traded sharp barbs and brutal put-downs at a supposedly light-hearted New York charity gala, with many in the well-heeled crowd turning on the Republican nominee midway through his remarks and showering him with jeers.
The annual white-tie Alfred E Smith Memorial Foundation Dinner – often the last time the US presidential nominees share a stage before election day – is traditionally a time when campaign hostilities are set aside.
But the night after their final presidential debate, Mr Trump, who had drawn big laughs earlier in the speech, appeared to lose the room as he repeatedly dug in with caustic swipes at Democrat Mrs Clinton, drawing rare boos at an event meant to raise money for impoverished children throughout New York.
He appeared to straddle the line when he talked about how “listening to Hillary rattle on and rattle on” had made him better appreciate his former nemesis Rosie O’Donnell. But he then seemed to cross it when he referred to her as “corrupt” during a lengthy riff on the FBI’s investigation into her use of a private email server as US secretary of state.
“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? Pretty corrupt,” he said to loud boos and at least one call demanding he get off the stage.
He then almost appeared to segue into the standard attack lines of his rally speeches, setting aside jokes to bring up material contained in hacked Clinton campaign emails.
“Hillary believes that it’s vital to deceive the people by having one public policy and a totally different policy in private,” he said to growing jeers. “Here she is tonight, in public, pretending not to hate Catholics.”
Mrs Clinton also veered into personal digs, making one joke in which she said the Statue of Liberty, for most Americans, represented a symbol of hope for immigrants.
“Donald looks at the Statue of Liberty and sees a ‘4’,” she said. “Maybe a ‘5’ if she loses the torch and tablet and changes her hair.”
Mr Trump and Mrs Clinton sat one seat apart for the evening, with New York’s Cardinal Timothy Dolan acting as the only buffer. And when they entered and took their seats, they did not greet each other or make eye contact, though they did shake hands later.
Cardinal Dolan later called his seat “the iciest place on the planet”.
Most eyes were on Mr Trump, who infamously glowered through Barack Obama’s jokes at his expense during the 2011 White House Correspondents Dinner and is not known for being self-deprecating.
But some of his jokes landed well, drawing laughs from both the crowd and Mrs Clinton.
His biggest laughs came as he talked about Michelle Obama getting rave reviews for a recent speech. “They think she’s absolutely great. My wife Melania gives the exact same speech, and people get on her case,” he said to whoops and laughs.
And some of his attack lines flashed a sense of humour that has been mostly absent from the gruelling campaign.
Mrs Clinton was the first one to laugh when Mr Trump joked that she had bumped into him earlier in the night “and she very simply said ‘Pardon me'” – an unsubtle reference to the Republican nominee’s frequent declarations that his opponent should go to jail.
Mrs Clinton, meanwhile, was more self-deprecating than Mr Trump, joking that she had taken a break from her “usual nap schedule” to attend and suggesting that the audience should be pleased she was not charging her usual fee for speaking in front of potential donors.
But she also landed some digs at Mr Trump, a few of which drew scattered jeers. She said she understood why he was wary of teleprompters because they can be difficult to follow and “I’m sure it’s even harder when you’re translating from the original Russian”.
The dinner is named after the former New York governor, who was the first Catholic to receive a major party nomination for president when he unsuccessfully ran in 1928. And fittingly for an event named after a man nicknamed “The Happy Warrior”, the occasion has produced dozens of memorable presidential jokes – and sincere moments of goodwill that have remained largely absent from the 2016 campaign.
“I can’t wish my opponent luck,” John McCain said in 2008, turning towards Mr Obama, “but I do wish him well”.
Meanwhile, figures show both White House contenders have been spending furiously at the November 8 election looms.
Defying his notorious stinginess, Mr Trump more than doubled his campaign spending last month compared with August, burning through about $70m as his standing in polls and among fellow Republicans dropped.
And Mrs Clinton spent even more, almost $83m.
New finance reports filed with the Federal Election Commission outlined their dramatically different approaches to the quest for the White House.
Mr Trump, while putting more money than ever into advertising, spent a fraction of the $66m Mrs Clinton poured into media buys.
Her payroll topped 800 people, coming in as her second-highest expense of the month, about $5.5m. Mr Trump paid about 350 employees and consultants. He has outsourced most of his on-the-ground voter contact to the Republican Party.
The New York billionaire property mogul has bragged until recently about his low-cost campaign and dismissed the need for television ads and polling services. But in September, he paid $23m for commercials.