The club's dinner brings together Washington's media elite, with noteworthy politicians typically attending, as well.
Despite being held by a media organization that raises scholarship funds for journalism students, the dinners are generally closed to cameras. Organizers only allowed a select few pool reporters to enter while the President spoke.
The lack of media glare allows guests to let some of their guard down, perhaps unleashing a few more jokes than they might if the cameras were rolling.
At one point Obama, clad in a white tie, predicted he would get more laughs this year than in the past.
"I'm not saying I'm any funnier. I'm saying weed is now legal in D.C.," he said.
Voters in the District of Columbia legalized small amounts of marijuana last year, much to the chagrin of some in Congress.
The President also touched on the controversy
over the archiving of Clinton's emails while she was secretary of state. Obama lamented that while he was once a tech-savvy candidate, Clinton now seemed more up to speed.
"Now I'm yesterday's news, and Hillary has got a server in her house. I didn't even know you could have one of those in your house. I am so far behind. Did you know that? I would have gotten one," he joked.
The domain name for Clinton's private email address was @clintonemail.com.
Obama wasn't the only politician attending this year's dinner. Wisconsin Gov. Scott Walker also dropped in. He's of course rumored to be in contention to run for president in 2016.
Walker, a Republican, acknowledged some headlines of his own, like when Rudy Giuliani said at a Walker event last month that he doesn't think Obama loves America. To date, Walker hadn't said whether he agreed with Giuliani or not.
"I want to get this out of the way once and for all. I believe President Obama loves America and every single American in it. Except for Rudy Giuliani," Walker said, according to a transcript provided by his staff.
"If I did not love America, I wouldn't have moved here from Kenya," Obama later countered in a joking reference to unsubstantiated theories
that he wasn't born in the United States.
Every president since 1885 except for Grover Cleveland has attended the 130-year-old organization's dinner. Obama has attended three times as president and last attended back in 2013.