Donald Trump and video gay sexHillary Clinton took to the podium at the Waldorf Astoria hotel Thursday for a charity dinner at which gentle roasting was the order of the day.
One problem, however: Trump didn't get the memo.
SEE ALSO: Clinton and Trump share awkward charity dinner night after fiery debateThe Republican nominee's speech started well enough, with Trump giving shout-outs to Sen. Chuck Schumer ("He used to love me when I was a Democrat") and New York mayor Bill De Blasio ("I haven't been doing so much of the real estate.")
"A special hello to all of you in this room who have known and loved me," he continued, gaining massive laughs whether intentionally or not. If it was self-deprecating wit, it was incredibly dry.
He then told the crowd that modesty was his best quality, before launching into a Jesus joke describing himself as a carpenter working for his father.
"This is corny stuff," he said, before dropping a genuinely funny gag about Hillary bumping into him backstage and saying "pardon me."
"I very politely replied, let me talk to you about that after I get into office," he added. "Just kidding, just kidding. She said if somehow she gets elected, she wants me to be either her ambassador to Iraq or Afghanistan. It's my choice."
He even dropped in a joke about his "beautiful hands."
Original image has been replaced. Credit: Mashable Then things took a darker turn. After addressing his "nasty women" comment from Thursday's debate, and joking that he doesn't think so badly of Rosie O'Donnell any more, Trump launched into a series of attacks that departed from the traditionally friendly format of the night.
He called out the media, apparently pointing to top brass at the New York Times, CNN, NBC and the Washington Post assembled in the room.
"Here she is tonight, in public, pretending not to hate Catholics."
He hit out at Clinton on her emails. "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," he said to boos from the crowd.
In response to that he quipped: "That's OK, I don't know who they're angry at, Hillary, you or I. For example, here she is tonight, in public, pretending not to hate Catholics."
The Alfred E. Smith Memorial Foundation dinner, at which he was speaking, is a fundraiser for Catholic charities working with needy children.
Another misjudged line: "Hillary's belief that it takes a village, which only makes sense in Haiti when she takes a number of them."
And another: "According to her sworn testimony, Hillary has forgotten more things than most of us will ever, ever know -- that I can tell you."
"We're having some fun here tonight," he added after the latter, while the audience in the room vehemently disagreed.
Bonus: A recap of some of the best and worst jokes from the dinner