POTUS brought the house down in front of almost 3,000 guests at the Washington Hilton ballroom in Washington, D.C., on Saturday, including celebrities like Kendall Jenner, Kerry Washington, and Emma Watson.
Politicians at the event included Vice President Joe Biden, Democratic presidential candidate Bernie Sanders, Secretary of State John Kerry and New York Mayor Michael Bloomberg.
After a blooper reel showed some of Obama's past errors -- including calling Kanye West a "jackass" when he didn't realize a mic was still on -- Obama took to the stage in a sharp blac-and-white tux to gives his final WHCD opening remarks.
"8 years ago, I said it was time to change the tone of our politics. In hindsight, I clearly should have been more specific," he said.
No one was safe from the President's jokes, including little Prince George, whom he met at Kensington Palace on April 22, where the little royal shook hands with Obama while wearing an awe-inducing robe.
"Even some foreign leaders have been giving me grief," Obama said. "Last week, Prince George showed up to our meeting in his bathrobe. That was a slap in the face. A clear breach of protocol."
He continued to joke about his trip over the pond, admitting, "Although, while in Englandm I did have lunch with Her Majesty the Queen. Took in a performance of Shakespeare. Hit the links with David Cameron. Just in case anybody is still debating whether I'm black enough … I think that settles the debate."
Obama even took on the current presidential race, poking fun at Bernie Sanders' "Feel the Bern" slogan and joking that Hillary Clinton's attempts to connect with young voters make her look like an old aunt joining Facebook.
An illustration of Clinton's logo pushing a giant rock uphill came on screen with a new motto, "Trudge up the Hill," with Obama noting, "Hillary's slogan has not had the same effect."
He also questioned where Republican presidential hopeful Donald Trump was this year while explaining that the businessman does have foreign policy experience. "He has spent years meeting with leaders from around the world: Miss Sweden, Miss Argentina, Miss Azerbaijan," Obama said.
And even Kendall Jenner got a shout-out from the President. "We had a chance to meet backstage. She seems like a very nice young woman," Obama told the audience. "I'm not exactly sure what she does, but I am told my Twitter mentions are about to go through the roof."
The dinner was hosted by The Nightly Show host Larry Wilmore, who made plenty of his own cracks at POTUS, including taking digs at Obama's age.
"President Obama's hair is so white it's started saying 'All Lives Matter,'" he said. "He's breaking stereotypes. Black does crack."
Then again, Obama, 54, was a pretty good sport about his gray hairs as well. "Michelle has not aged a day. The only way you can date her in photos is by looking at me," he cracked.