It was supposed to be a light-hearted New York charity gala, where traditionally campaign hostilities are set aside for one night while everyone just enjoys some dinner.
But that was definitely not the case when it came to Donald Trump and Hillary Clinton. Actually, the pair ended up trading some pretty brutal put-downs at the annual white-tie Alfred E Smith Memorial Foundation Dinner - an event meant to raise money for impoverished children throughout New York.
Although Trump had managed to draw some big laughs early in his speech, many people in the crowd turned on the Republican nominee to boo him when he seemed to cross the line.
He appeared to lose the room as he repeatedly dug in with caustic swipes at Democrat Clinton, referring to her as "corrupt". That was 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 started 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."
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."
In another dig, 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".
Trump and Clinton sat one seat apart for the evening, with New York's Cardinal Timothy Dolan acting as the only buffer. When they entered and took their seats, they didn't greet each other or make eye contact, though they did shake hands at the conclusion of the roast.
Cardinal Dolan later called his seat "the iciest place on the planet". Yeah, we can imagine it would have been a bit awkward at times...
Some of Trump's jokes did draw laughs from both the crowd and Clinton though.
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.