The New York Times will boycott the event for the third year in a row, citing concerns that the dinner gives the impression that reporters are cozying up to administration officials.
Leno may be the featured comedian on Saturday night, but Obama will try to give him a run for his money by showcasing his own comedic chops with the traditional presidential stand up routine, a staple of the spring black tie dinner season in Washington.
Eric Schnure, a veteran political speechwriter and comedy writer, said that one direction Obama could go is to play off of the recent reports about tense relations between the White House and the reporters who cover it.
"That's safe ground for him to joke about because it touches folks in the audience and it allows him to be self-deprecating, which obviously works so well in these events," Schnure said.
Sure, Obama could go too far – a joke last year about the gathered reporters all voting for him fell a bit flat, perhaps because it hit too close to home to a sensitive press corps.
"That's the secret to all humor, isn't it? Doing that delicate dance," Schnure said. "Finding the right tone and the right balance. I would think that without touching on that or acknowledging that, it because a bit obvious in its absence."
Such routines require a significant amount of preparation, rehearsal and guts. So why do politicians ever agree to do this? Why take a chance at jokes falling flat and routines bombing?
"There is a tradition to doing these things, a prestige to do these kinds of events," Schnure said. "I think the driving force is that politicians are in the business of having people like them and it's not as much getting laughs as it is being liked."
Several comedy writers who have worked with lawmakers on these kinds of appearances told ABC News that a stand-up comedy act is a powerful tool to show that politicians don't take themselves too seriously, and it gives them a chance to bask in a more forgiving spotlight.
Landon Parvin, who has written comedy routines for several Republican presidents, including former President George W. Bush, said these speeches are "another means for the public to judge the president."
"People don't get to see a president in that kind of humorous mode very often," Parvin said.
Most presidents have used the occasion to lighten up a bit and poke fun at themselves, as Presidents Bill Clinton and George W. Bush did in their dinner appearances. Self-deprecating humor is always the gold standard for such an event.
At his last dinner in 2000, Clinton joked about what life would be like after he moved out of the White House.
"But a year from now, I'll have to watch someone else give this speech. And I will feel an onset of that rare affliction, unique to former presidents. AGDD -- Attention-Getting Deficit Disorder," Clinton said.
Over his two terms, Bush provided ample material for the late-night comedians and the correspondents' dinner gave him a chance, for one night a year, to show that can get in on the joke too.
"You know, I'm not sure what I'm going to do next. After he left office, Vice President Gore won an Oscar and the Nobel Peace Prize. Hey, I don't know, I might win a prize -- Publishing Clearinghouse or something," he said to laughter.
Schnure said that even with a potentially cynical crowd like the Washington press corps, it is still a crowd that wants to see the president pull off a successful comedy bit.