The seeds of Republican presidential nominee Donald Trump's widely-panned performance at the Al Smith Memorial Foundation Dinner in New York City on Thursday may have been sown five years earlier at the 2011 White House Correspondents Dinner.
That evening, in the midst of Trump's public crusade to raise doubts about President Barack Obama's citizenship, he was eviscerated on the dais first by the president himself and then by late night host Seth Meyers as he sat stone-faced and seething, according people in attendance. The theory goes that the germ of a future presidential run was planted in Trump's mind that night -- he would not only run against the very establishment media elites that populated that audience, but overthrow them.
But a funny thing happened on his way to the White House, his lack of self-deprecation began to be viewed as a real Achilles heel, never more so than in his three prime-debates opposite Hillary Clinton, (a candidate often caricatured for her supposed lack of humor, too), where a myriad of physical tics and grimaces, coupled with his frequent interruptions and non-sequitur insults ("such a nasty woman') seemed to exacerbate voters' concerns about his temperament, not quell them.
Following his badly reviewed debate performances Trump not only lashed at familiar right wing targets like the press, but he also took on "Saturday Night Live," a show he had hosted just last year, and called for its cancellation after a sketch mocking him rubbed him the wrong way. Pundits began to point out that Trump had rarely, if ever, been photographed laughing in public and Democratic nominee Hillary Clinton's either giddy or dumbfounded reactions to his recalcitrance became candy for Internet meme makers.
Meanwhile, when Trump has drawn laughs recently they were unintentional, like when he said "nobody" has more respect for women than him, and there were titters at the third presidential prime-time debate.
The Al Smith Dinner may have been Trump's last chance to prove to the American public that he could take himself down a peg with panache -- MSNBC's Chuck Todd called it a "gimme" -- but the consensus has begun to form that after a few well-received jokes he failed to read the room.
"Trump got the memo to smile, but he didn't laugh. I haven't seen him do that thing that human beings do which is laugh at things," Democratic Sen. Al Franken, a former comedy writing legend and "SNL" veteran, told MSNBC's Rachel Maddow after watching the candidates' performance on Thursday. "There were some good jokes there and there were some hits at her that had no joke work whatsoever."
For some comedians who have been following the 2016 race, Trump's bombing was less surprising than it was disappointing, since he could have shown a side of himself the American public has yet to see.
"I think we've all sort of just been waiting for any inclination that he's in on the joke. We're all sort of desperate for some semblance of sanity," comedian Sarah Hartshorne told NBC News. "He was so funny at first and it quickly got so scary."
Trump's 'jokes' about Clinton being corrupt, allegedly being fired from the Watergate Commission and "hating Catholics" drew boos and hisses from an audience that historically has skewed conservative. The Al Smith Dinner, however, has been held up as a rare evening of gentle bipartisan ribbing in a heated election season.
Beyond raising questions about who wrote Trump's material, Hartsthorne hopes that both candidates performances on Thursday will also highlight what she considers the gender politics at play (the double standard of affability she, and many others, believe Clinton has been held to) and the flaws inherent in some of our political traditions and expectations.
"On one level I don't think a president should be self-deprecating," she said, suggesting the desire to have a 'funny' president is somewhat indicative of anti-intellectualism. "At the same time when I see the incredible hubris, the lack of modesty and [Trump] has to joke about it, when forced, it's good."
Part of the problem that a President Trump or Clinton will face, according to comedian Camille Theobald, is that they both have an incredibly tough act to follow -- President Barack Obama.
"Obama's been one of the most suave presidents ever. I think the pressure is definitely on," she said. "Obama had great writers but he also had a great sense of humor to begin with."
Theobald, who has recently been impersonating Clinton on stage, would certainly benefit from a Democratic victory, but her bottom line aside, had Trump's unpredictable reactions to jokes at his expense (he did make it through a Comedy Central roast, and several other late night appearances) been more measured, she might have been more receptive to his message.
"I think his biggest weakness is his ego and his habit of insulting people all the time," she said. "That said, I watch some of his campaign speeches and nothing has made me laugh harder. A lot of things he says are hilarious, I just don't think he means them to be."
"I think it's a terrible idea to diagnose people you haven't met, so take this with 400 gains of salt, but he's a narcissist," said Harstshorne. "Humor is very hard for narcissists."
That said, for comedians, Trump will still be a source of laughs for the foreseeable future, even if he doesn't pull off a come-from-behind victory on November 8th.
As Theobald put it: "I don't think he's ever going to shut up."