Donald Trump on Thursday night eschewed decades of tradition by offering a tough takedown of Hillary Clinton at the Al Smith dinner, and his remarks notably lacked self-deprecating humor.
In doing so, Trump missed an opportunity to take some of the heat off his campaign as it struggles through the final weeks of the race.
He opened with some more light-hearted remarks, referencing his "beautiful hands" and joking about how his crowds at rallies dwarf Clinton's.
"It's great to be here with 1,000 wonderful people. Or, as I call it, a small, intimate dinner with some friends. Or as Hillary calls it, her largest crowd of the season," Trump said, to which Clinton laughed.
But the mood turned dour when Trump began to directly take on Clinton.
He said Clinton wants him to be her ambassador to Iraq or Afghanistan -- "it's my choice."
Trump made reference to calling Clinton a "nasty woman" in Wednesday nights' presidential debate -- and compared his feelings about Clinton to his years-old beef with Rosie O'Donnell.
"After listening to Hillary rattle on and on and on, I don't think so badly of Rosie O'Donnell anymore. In fact, I'm actually starting to like Rosie a lot," he said.
He cracked a joke about Melania Trump's plagiarism of a Michelle Obama speech when she spoke at the Republican National Convention in Cleveland this summer.
"Michelle Obama gives a speech and everyone loves it, it's fantastic. They think she's absolutely great. My wife Melania gives the exact same speech and people get on her case," Trump said, groaning that he'd be in trouble at home after the event.
"She didn't know about that one," he said, looking at his wife -- and then to Cardinal Timothy Dolan, sitting nearby. "Cardinal, please speak to her," he said.
Midway through his remarks, the crowd turned on Trump -- booing as he attacked Clinton's use of a personal email server and accusing her of ducking FBI questions.
"According to her sworn testimony, Hillary has forgotten more things than most of us will ever, ever know -- that I can tell you," Trump said, to crickets. "We're having some fun here tonight."
"I wasn't really sure if Hillary was going to be here tonight because, I guess, you didn't send her invitation by email. Or maybe you did, and she just found out about it through the wonder of WikiLeaks," Trump said. "We've learned so much from WikiLeaks. For example, Hillary believes that it is vital to deceive the people by having one public policy and a totally different policy in private."
When the audience booed at that line, Trump said, "That's OK, I don't know who they're angry at,
No handshake
The two did not shake hands or acknowledge each other on their way to their seats.
During his introductory remarks, Al Smith IV said Trump asked Clinton how she was before they came on stage together. "I'm fine," Smith joked Clinton said. "Now get out of the ladies' dressing room."
Both Clinton and Trump laughed. But the GOP nominee's wife, Melania Trump, did not seem as impressed with the comment about the swirling accusations around the Republican nominee.
As Al Smith IV's locker room joke hit, Trump swayed to his side, leaning into Melania and laughing off the joke with a knowing wince.
After urging the guests to turn off their phones, Smith said, "Secretary Clinton has told me that Donald is welcome to tweet away. Apparently when Donald tweets, it makes both of them happy."
Dolan spent most of the time speaking with Clinton and almost had his back turned to Trump.
Former New York City mayor and Trump surrogate Giuliani came up behind Trump at one point, grabbed his shoulders and whispered something to him and Melania Trump.
Minutes before he was set to address the room, Trump could be seen writing down notes on a piece of paper and then showing them to his wife. It wasn't clear if he was editing remarks or writing on a blank piece of paper.
Bitter rivals
Historically, the dinner has been a good-natured roast -- one with plenty of jokes, to be sure, but none that break with the white-tie gala's sense of decorum.
Thursday night is different, for one simple reason: Clinton and Trump loathe each other.
The two declined to shake hands at the beginning and end of Wednesday night's presidential debate, one where Trump called Clinton "such a nasty woman" and Clinton called Trump a "puppet."
Trump, in particular, has struggled to laugh at jokes told at his expense.
He famously glowered at President Barack Obama, who ribbed him at the 2011 White House Correspondents Dinner over his years of stoking false conspiracy theories about Obama's birthplace.
"He can finally get back to focusing on the issues that matter, like, did we fake the moon landing? What really happened in Roswell? And where are Biggie and Tupac?" Obama said then. Minutes later, he took a swipe at Trump's role as host of "Celebrity Apprentice."
Trump has also complained about Alec Baldwin's portrayal of him on "Saturday Night Live." After last weekend's take on Trump's performance in the second debate, he tweeted: "Watched Saturday Night Live hit job on me.Time to retire the boring and unfunny show. Alec Baldwin portrayal stinks. Media rigging election!"
A long-standing tradition
The Alfred E. Smith Memorial Foundation Dinner -- held the third Thursday of every October -- is a tradition in American presidential politics and marks the last time the two nominees share a stage.
Named for the former New York governor and first Catholic to receive a major party nomination when Democrats tapped him to oppose Herbert Hoover in 1928, the Manhattan event has an attendance of more than 1,500 donors who give more than $3,000 each to Catholic charities for tickets.
Then-Texas Gov. George W. Bush joked about the well-heeled crowd in 2000, when he attended as the Republican nominee.
"This is an impressive crowd. The haves and the have-mores. Some people call you the elite. I call you my base," he said.
The dinner became a mainstay in presidential politics in 1960, when both John F. Kennedy and Richard Nixon attended.
"I had announced earlier this year that, if successful, I would not consider campaign contributions as a substitute for experience in appointing ambassadors. Ever since I made that statement, I have not received one single cent from my father," Kennedy joked about his politically-connected family that year.
In 2000, Al Gore told another memorable joke -- at the expense of Clinton, nearing the end of her successful Senate run in New York.
"I did think it was effective when I weaved in stories of real people in the audience and their everyday challenges. Like the woman here tonight whose husband is about to lose his job. She's struggling to get out of public housing and get a job of her own. Hillary Clinton, I want to fight for you," he said.
In 2008, Arizona Sen. John McCain joked about media perceptions of then-Illinois Sen. Barack Obama. "Maverick I can do, but Messiah is above my pay grade," he said.
At the last Al Smith dinner featuring presidential candidates -- 2012 -- Obama and GOP nominee Mitt Romney joked about themselves and each other.
"Usually when I get invited to gatherings like this, it's just to be the designated driver," said Romney, who is a Mormon.
In a jab at Obama, he pointed to the national debt, saying: "By the way, in the spirit of Sesame Street, the President's remarks tonight are brought to you by the letter O and the number 16 trillion."
Obama poked fun at his own lackadaisical performance in their first presidential debate. "I felt really well rested after the nice long nap I had in the first debate," he said.
And he chided Romney's vast personal wealth. "Early today, I went shopping at some stores in Midtown," Obama said. "I understand Gov. Romney went shopping for some stores in Midtown."