"After the midterm elections, my advisers asked me, 'Mr. President, do you have a bucket list?' And I said, 'Well, I have something that rhymes with bucket list.'"
The audience started to get the joke. And then the president continued: "Take executive action on immigration. Bucket. New climate regulations. Bucket, it's the right thing to do."
Add to that list: Normalizing relations with Cuba and pushing through trade legislation by teaming up with Republicans and taking on unions.
That's no joke.
Beyond policy, Obama seems more willing lately to just say it like he sees it. Take last week when he shouted down a heckler at a White House reception.
"Hold on a sec," Obama began. "OK. You know what? Nah, nah, nah, nah, nah, nah. No, no, no, no. Hey, listen, you're in my house. ... You're not going to get a good response from me by interrupting me like this. No. Shame on you, you shouldn't be doing this."
After the heckler was escorted out, Obama kept talking.
"As a general rule, I am just fine with a few hecklers," the president said. "But not when I'm up in the house. My attitude is if you're eating the hors d'oeuvres..."
Then he turned and looked at Vice President Biden, who was nodding along.
"You know what I'm sayin'?" Obama asked.
Biden obliged. "I know what you're saying," the vice president said back.
"And drinkin' the booze," Obama continued. "I know that's right. Anyway, where was I?"
On the podcast, Obama alluded to his youthful drug use and talked extensively about his own racial identity. And when talking about racism in America, he used a word that is potentially offensive to some.
"Racism," Obama said. "We are not cured of it. And it's not just a matter of it not being polite to say 'nigger' in public. That's not the measure of whether racism still exists or not."
It's a point Obama has made before. But never quite so bluntly. Then on Friday, Obama did something else it's hard to imagine him doing earlier in his presidency.
In front of thousands at the funeral of the Rev. Clementa Pinckney, who was one of nine people killed in the massacre at a historically black church in Charleston, S.C., he surprised mourners when he began to sing "Amazing Grace." Eventually, the crowd was on its feet:
Sure, he might have been off key in spots, but it simply didn't matter. For the record, he has sung before as president — or at least began to.
Here he was in 2012 beginning to sing Al Green's, "Let's Stay Together":
A month later, there he was at the White House singing, "Sweet Home Chicago" with B.B. King:
But he's never gone on quite so long as he did Friday in Charleston.
Obama, like other presidents before him, has complained about the controlled and cloistered nature of the presidency. It's why last year when he ditched his motorcade and went for a walk to the Department of the Interior, stopping to shake hands with tourists, he declared, "The bear is loose!"
In Obama's WTF podcast interview, he described a certain fearlessness that comes after six-and-a-half years in the White House.
"I've been in the barrel tumbling down Niagara Falls," Obama said, "and I emerged, and I lived, and that's such a liberating feeling."