Obama Was His Usual Hilarious Self On 'Letterman'

If there's one thing you can say about POTUS, the man's got a great sense of humor. You definitely saw it last month at the White House Correspondents' Dinner when he took jabs at anyone and everyone on Capitol Hill, and the president proved once again Monday that he never disappoints when it comes to his late-night appearances. President Obama's funniest moments on Late Show With David Letterman came during the light-hearted banter between the two men, and the part-sentimental fun was another reminder of how little time was left in both of their historic careers.

Now that he's well into the "fourth quarter" of his presidency, Obama gave his third and last appearance on the Late Show as Leader of the Free World. Letterman is also in the final weeks of his 22-year tenure running the CBS' late-night show, with his last night coming on May 20. While much of the conversation did veer on the more serious side of things — Letterman and Obama went in-depth about Baltimore and free trade agreement (thankfully speaking for all of us, Letterman admitted he didn't really know too much about them) — there were definitely some moments that had you chuckling.

On Michelle Obama

First Lady Michelle Obama graced the Late Show set last week to talk about her work with military families, and Letterman didn't hesitate to let Obama know how much he was delighted with his other half. Obama, who has never held back on giving his wife credit where credit is due, was happy to acknowledge how popular Michelle is — compared to him.

I know you like Michelle a little bit more than me. Which is okay. And I assure you, you’re not alone.

On Elections 2016


As the outgoing president, Obama will be an important player among Democrats to advocate for whoever the party decides to nominate (cough, Hillary). He encouraged all voters, regardless of their party affiliation, to get educated on the candidates and to turn out to the polls. But he was quick to correct Letterman on how much time he actually had left in his presidency.

It’s less than two years... not that I'm counting. But I just want to make sure you don’t show up like in the middle of January to vote, and everybody will be like, "What happened?"

On Obama Retiring

One thing Obama and Letterman have in common is that they're both about to exit the biggest jobs of their careers. Which is why, of course, they took the time to share their retirement plans. So what's a day in the life of a retired Obama? Chilling with Letterman, playing dominoes, and hitting up Starbucks.

Well, I was thinking you and me could play some dominoes together. We can, you know, go to the local Starbucks, swap stories.

On Letterman Retiring

While Letterman insisted his domino chops could take Obama's (I'd pay to see that match), the late-night host decided to go a more sort-of serious route, saying he planned on teaching law at Columbia University. Obama, who actually received his bachelor's degree from the New York school and later taught law at the University of Chicago Law School for well over a decade, offered to sign up.

I'd be interested in sitting in on that class. That would be a hoot.

Really, Obama is just one of us, and I for one am going to miss his late-night hits when he officially bows out of the White House.

Images: CBS; Getty Images (1)