The 5 Most Uncomfortably Awkward Trump Moments During Last Night's Charity Event

The annual Al Smith Dinner has become a beloved tradition in political circles the past 30 years. Whether you love or hate politics, there’s something really satisfying about seeing a famous political leader get up on stage and tear themselves down a bit with some self-deprecating jokes.

Every four years, the dinner gets national attention when the two presidential nominees take the stage just weeks before the election. Even Al Gore and George W. Bush put on a display of grace and humor while deadlocked heading into the 2000 election. But once again, Donald Trump made history by turning a seemingly simple and fun event into an awkward nightmare.

Things started off decently enough, with Trump getting huge laughs from the audience and Clinton herself when he made this joke about his wife Melania plagiarizing a Michelle Obama speech:

"Michelle Obama gives a speech and everyone loves it, it's fantastic," Trump said. "They think she's absolutely great. My wife, Melania, gives the exact same speech, and people get on her case!"

But then things went downhill fast when Trump decided to put the joke book aside and started taking direct personal shots at Clinton:

"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."

The crowd very awkwardly began booing Trump, who undeterred continued his suddenly very political and personal attacks.

"Here she is tonight, in public, pretending not to hate Catholics," he said to gasps.

“Hillary is so corrupt she got kicked off the Watergate commission,” he added, as Clinton’s face went from bemused laughter to stone cold.

"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. After more boos erupted, he tried to deflect the reaction, deadpanning, “We’re having some fun here tonight."

Finally, recognizing he’d lost the room, Trump turned on the audience themselves, whining about how many celebrity friends he used to have.

"Suddenly, [they] decided when I ran for president as a Republican that I've always been a no-good, rotten, disgusting scoundrel. And they totally forgot about me."

Afterward, the event’s organizer Al Smith V, commented on the truly unprecedented nature of the audience turning on Trump:

"Donald had some very solid minutes early on and eventually he crossed the line and took it a little too far," Smith said in an interview with CNN. "Hillary, on the other hand, was able to laugh at herself and at the same time not underplay any of the serious things Donald Trump has said or done."

Taking the stage after Trump, Clinton tried to salvage the night but it was clear that people were uncomfortable and ready to get out of the room, and this terrible, terrible campaign, as soon as possible. Nonetheless, she got in a few zingers, some at her own expense:

"This is such a special event that I took a break from my rigorous nap schedule to be here," Clinton said.

And referencing her own perceived ties to Wall Street, she added, "It's a treat for all of you, too, because I charge a lot for speeches like this."

And she, of course, had a few hot lines for Trump, like this beauty:

"People look at the Statue of Liberty and they see a proud symbol of our history as a nation of immigrants. A beacon of hope for people around the world," Clinton said. "Donald sees the Statue of Liberty and sees a 4. Maybe a 5 if she loses the torch and tablet and changes her hair.”