Washington: He's a real estate mogul, a reality show pioneer and now a political phenom on his way to becoming the Republican presidential nominee.
And that success sets Donald Trump up for a different role on Saturday night: punch line.
As President Barack Obama polishes his annual -- and final -- tart-tongued stand-up riff for the White House Correspondents' Association dinner, Washington is salivating at the prospect of a sequel to his blistering evisceration of Trump in 2011. The President used that speech to publicly ridicule Trump — who was in the audience — for the billionaire's claims that Obama was not a natural born American and was therefore disqualified from being President.
"Obviously, we all know about your credentials and breadth of experience," Obama said, slamming Trump for his supposed displays of leadership on "Celebrity Apprentice."
"These are the kind of decisions that would keep me up at night. Well handled sir, well handled," Obama said sarcastically.
D.C.'s chance to be hip
The dinner is Washington's annual opportunity to pretend it's hip. Reporters mingle with Hollywood stars, top sports figures, business leaders, administration officials and lawmakers who normally avoid the press. But it's also derided by critics as a sign of an overly cozy cabal of Washington insiders -- frustration that has contributed to the rise of political outsiders like Trump and Democratic presidential contender Bernie Sanders this year.
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In fact, the most unorthodox presidential race in modern history points to a comedy conundrum faced by Obama in his farewell address to the Washington insider love fest that the annual dinner has become. How do you satirize -- and in the process land political blows -- on a campaign that has lifted American politics to new heights of self-parody?
"In some ways it is strange, because this election campaign is so farcical, so exaggerated," said David Litt, who was the lead writer on Obama's White House Correspondent's Association speech between 2012 and last year.
"What outrageous thing can you say about Donald Trump that Donald Trump has not already said?" said Litt, who now runs the Washington operation of the comedy website "Funny or Die."
The media coverage that the dinner now whips up makes it a potboiler of political ambition. Some journalists have suggested that Trump's presidential yearnings began burning brighter in that moment of public humiliation back in 2011.
Whether that's true or not, Trump will not be taking any chances of a repeat -- choosing to stay away from the dinner this year as he campaigns ahead of Tuesday's Indiana primary, which could put him on the path to clinching the GOP nomination. (Sanders will be the only current presidential candidate at this year's dinner.)
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Trump told The Hill in an interview that he had been invited by multiple news organizations but decided not to go because "I would have a good time and the press would say I look like I wasn't having a good time."
He also complained that contrary to news reports at the time, he enjoyed Obama's roasting and was "honored" by the attention.
While the Republican front-runner is high on Obama's comedy hit list, White House sources made clear that Trump won't be alone on the firing line.
That means Sanders, Ted Cruz, Hillary Clinton and the rest of the gang -- as well as the media whose saturation coverage is blamed by some for Trump's rise -- might also find themselves in the spotlight by the time Obama is done.
'So much to make fun of'
"It's a good thing for Washington to take itself down a peg for a night," said chief White House speechwriter Cody Keenan, who oversees the three-week-long process of putting the speech together. "There's nobody in America who would say 'hey, these politicians are poking fun at each other too much.' Because there's so much to make fun of!"
But don't expect overt accusations of racism and sexism from Obama at the podium on Saturday night. Aides say the President believes that outright cruelty would be inappropriate and sees humor as a much more effective weapon in debunking Trump.
The 2016 campaign has served up plenty of material.
Trump boasted about the size of his manhood and suggested Fox News anchor Megyn Kelly had blood coming out of her "wherever."
President Obama and Seth Myers joke about Trump 02:12
Another candidate -- Sen. Lindsey Graham -- smashed his cellphone with a golf club. Ben Carson stood by his view that the pyramids were built to store grain. Cruz munched on bacon sizzled on the muzzle of a machine gun and Clinton misfired spectacularly by joking she had wiped her notorious email server "with a cloth."
Then there was the time when Jeb Bush validated the "low energy" nickname bestowed on him by Trump by pleading with a snoozing crowd to "Please, clap."
And Chris Christie's tortured facial gymnastics on stage alongside Trump during one of his election-night tirades is just begging to be lampooned by the president.
Meeting expectations
Given the anticipation building around an Obama takedown of Trump, the president is facing a familiar assignment -- meeting expectations he himself has raised. But those who have worked closely with him are not sweating the result, pointing to the President's instinctive comic timing and delivery of searing one liners.
"He can read a room in a way I think is impossible to teach," Litt said.
It's one of the worst kept secrets in Washington that presidents and first ladies dread the evening -- which amounts to three hours on stage at the head table while guests watch and they swap awkward small talk with journalists who earn a living taking pot shots at their presidency.
Still, once he starts his speech, almost every President finds the spotlight invigorating.
The lead writer on this year's address is Tyler Lechtenberg, a former sportswriter who joined the Obama campaign in 2007 in Iowa and who also worked as a speechwriter for First Lady Michelle Obama.
By now, the administration's speechwriting process is tried and tested. Former Obama aides and speechwriters like Jon Favreau, Jon Lovett, Dan Pfeiffer, Tommy Vietor and David Axelrod -- as well as A-list comedy giants who the White House will not identify -- have all contributed jokes.
Litt said he typically started with over 500 gags -- only about 5% of which make it past the President's exacting gauge of what is appropriate and sufficiently funny make it into the final speech.
Obama's swagger
Expect some swagger from Obama this year. He's confounded the lame duck label that haunts second term presidents, has seen major initiatives like his opening to Cuba and nuclear deal with Iran come to fruition in the last year, and his approval ratings recently topped 50% for the first time in years.
In a way, the dinner speech is a small part of the legacy that Obama will pass on to his successor.
That's because, over the years, he's stretched the genre of the address itself, walking right up to the line of what is seen as acceptable sarcasm.
Since the days of Ronald Reagan, when the speech was more of a Johnny Carson-style late night monologue, Presidents have used the event to settle political scores in a way that they would never do in a more formal environment.
Bill Clinton, for example, used humor at his last correspondents dinner to defuse a narrative that he was a lame duck, posing in a film as a lonely president in a deserted White House, with his wife out on the Senate campaign trail.
George W. Bush turned his wit on himself, poking at perceptions he was dim and at his propensity to misspeak in speeches that are remembered as glimmers of levity in otherwise dark political times.
Obama has taken the self-mockery to another level, using humor to address sensitive issues, such as Trump's birtherism campaign and questions about his race and religion that would be out of place from a White House podium.
In 2009, he mocked his own reliance on teleprompters, reading out the stage direction "Pause for laughter."
A year later, when his political fortunes tanked, he joked: "I know my approval ratings are still very high in the country of my birth."
And last year, he lampooned claims that he was a secret Muslim by remarking on how tough it was to be President "all while finding time to pray five times a day."
A healthy dose of self-deprecation is vital to a successful speech. As past presidents have understood, it buys goodwill in the room and in the wider audience outside and takes the personal sting out of the assaults on political rivals.
"You have to do that before you poke fun of everybody else," said Keenan. "But he'll never be mean -- he doesn't want anyone to leave with hurt feelings."
But with Trump poised to capture the Republican nomination and a bruising campaign looming in the fall, it's too early to say who will get the last laugh.
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