Clinton and Trump trade barbs at Al Smith dinner. Who won?

A good-natured night turned awkward when Hillary Clinton fell short of President Obama's knack for humor, and Donald Trump told offensive jokes that he never really intended to be funny. 

First Look

At the annual Alfred E. Smith Memorial Foundation Dinner Thursday evening, presidential nominees Hillary Clinton and Donald Trump proved their relationship might be well past civility and good humor.   

In fact, Mr. Trump proved it is possible to get booed from the stage at a charity dinner.

The Al Smith Dinner is an annual white tie fundraiser, held on the third Thursday of October. And since Richard Nixon and John F. Kennedy spoke at the event in 1960, all presidential candidates (except for Bill Clinton) have followed suit, relishing the lighthearted event amid contentious campaigns. 

In honor of Al Smith, the former governor of New York and the first Catholic presidential candidate, who ran in 1928, proceeds from the event go to Catholic charities that support needy children.  

The dinner is also remembered for its speeches – the event is typically the last time presidential candidates share a room before election night, trading tongue-in-cheek roasts and self-deprecating jabs. 

"Ultimately, though, tonight is not about the disagreements Governor Romney and I may have," President Barack Obama said during his dinner speech in 2012. "It's what we have in common – beginning with our unusual names. Actually, Mitt is his middle name. I wish I could use my middle name." 

But Thursday’s event was different from years past, as camps on both sides are finding little to laugh about this campaign cycle.

As the now-famous red-sweater wearing audience member Ken Bone said on "Jimmy Kimmel Live," attending the second presidential debate felt like watching parents fight. "I had to kind of put my head down while Mom and Dad were arguing over Thanksgiving dinner," he said.

The Al Smith gala helped to elevate the tension to a new level of awkward.

"If the Al Smith Dinner in previous years has served as a respite from bitter campaign seasons, this year it may have failed to do so," notes NPR. 

And while she may not have President Obama’s natural sense of humor, Mrs. Clinton tried to follow suit, making fun of both her opponent and herself.

"Now I’m going to try my best tonight, but I understand I am not known for my sense of humor. That’s why it did take a village to write these jokes," said Clinton, with laughter from the crowd.

"You know, I’ve had the privilege of being at the Al Smith dinners in years past and I always enjoy it," she continued. "But, remember, if you’re not happy with the way it comes out, it must be rigged." 

And after telling the audience it’s is a treat for her to attend the dinner despite a "rigorous nap schedule," she added, "it’s a treat for all of you, too, because usually I charge a lot for speeches like this."

Clinton's speech was the funniest when she was making fun of herself. The lack of applause and laughter during Trump’s speech is probably because he failed to do the same. Instead, his one-liners and punch lines mirrored a typical campaign speech, often feeling inappropriate, unnecessary, and hitting a little too close to home.

"Here she is tonight, in public, pretending not to hate Catholics," said Trump, referencing a recent email released by WikiLeaks that included negative comments about Catholics by Clinton staffers. 

"Hillary believes that it’s vital to deceive the people by having one public policy and a totally different policy in private," added Trump, with boos from the crowd.

However, Trump did get laughter for a joke at his wife’s expense: 

"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!" 

But there was at least "one bright spot" from the night, adds NPR. Unlike the final debate, before the event concluded the two candidates shook hands – to applause.

This report includes material from the Associated Press.