"The problem is finding ones who don't do a lot of profanity -- I think a lot of us would love to get Chris Rock, for example, but his act is too extreme for the stodgy old White House dinner," she said.
One reporter quipped that beyond Obama and Leno, perhaps the biggest credit should go to WHCA president Ed Chen "for cutting down on the epic program and getting the audience to shut up and listen."
For the president and other politicians who dare to take a turn at comedy, such routines require a significant amount of preparation, rehearsal -- and guts.
So why do politicians ever agree to do this? Why take a chance that jokes will fall flat and routines will bomb?
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.
"There is a tradition to doing these things, a prestige to do these kinds of events," said Eric Schnure, a veteran political speechwriter and comedy writer. "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."
Schnure said that humor is one of the few things that can go a long way to humanizing a politician.
"It's an incredible opportunity to get a warm response from a crowd who is usually skeptical of you -- the media," said another veteran comedy writer. "And it's an incredible opportunity to be self-deprecating, which is really endearing."
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.
Rule #1 for politicians: "Don't be offensive."
The comedy should be "reassuring, not cutting," Parvin said.
The veteran comedy writer pointed out that while there is an inherent risk to standing in front of a large audience and trying to be funny, there is also a big payoff if successful.
"The reason they put themselves through it is if you are self-deprecating you get up there and say, 'The pressure hasn't gotten to me, I can laugh at myself," Parvin said. "The problems aren't so bad that I can't joke about what's going on.'"
The Gridiron Club's motto -- "Singe not burn" -- is the mantra that these writers adhere to.
For any comedian, there is a fine line between humor and offense. In a town like Washington, where every sentence a politician utters is parsed for hidden or partisan meaning, words really matter.
Schnure said that in order to avoid crossing that line self-deprecating humor is the "fail-safe method."
"Humor is a powerful weapon that is best pointed at one's self," he said. "If they are not willing to be self-deprecating, there is a great risk that people don't just think they're not funny but that they are mean."
Schnure said that the best place to start is to figure out what a politician is known for -- what is the Beltway caricature that can get some laughs?