POTUS' Funniest Moments, Ranked

When he leaves office in just over two years, President Obama will leave behind a legacy that includes picking up a collapsed economy, a major overhaul of American health care, and dozens of hilarious TV appearances. It remains to be seen how the first two accomplishments will affect history in the long run, but we know we'll be searching for the latter on YouTube for years to come. The president's legacy was also a major topic of discussion on Monday, when President Obama appeared on The Colbert Report to discuss Obamacare, the ever-rotating Secretary of Defense position, immigration, and more.

It was just the president's latest display of comedic gold, which will undoubtedly help Obama go down in history as at least our funniest president — approval ratings be damned.

Monday night's episode of Colbert Report opens with Obama taking on the role of the satirically conservative host. He cleverly pokes fun at himself while taking the opportunity to promote open enrollment for the new and improved Obamacare site. Obama (as Colbert) quipped:

Remember the original HealthCare.gov website? I think that's where Disney got the idea for Frozen.

Zing! And this was far from Obama's first microphone-drop-worthy one-liner. Over the years and several White House Correspondents' Dinners, as well as numerous talk show appearances and candid videos, Obama has gifted us with countless zingers. The infectious president, whose term coincided with the dawning of the social media age, is the first in U.S. history to have connected with the American people on this level. As an early tribute to the president's legacy, we're ranking President Obama's greatest comedy moments.

5. Obama Plays Daniel Day-Lewis in 'Obama'

In a sketch made for the 2013 White House Correspondents' Dinner, Obama plays Daniel Day-Lewis, who is cast to play Obama in Steven Spielberg's spoof follow-up to Lincoln. Watching Obama practice being himself in front of a mirror will blow your mind. And the joke about his ears? It sets the benchmark for self-deprecating humor.

4. Midterm Voting Love Triangle

In October, Obama was casting his early ballot for the midterm elections next to a fellow voter when her boyfriend walked by and said, "Mr. President, don't touch my girlfriend." Obama's reaction was priceless.

3. Obama Slow-Jams the News With Jimmy Fallon

When Obama appeared on Late Night With Jimmy Fallon, the two discussed the president's proposal to cap Stafford student loan interests ... by slow-jamming the news. What results is a sultry, veritable verbal orgy between Obama, Fallon, and the Roots — about student loans. Oh, and Fallon calls him the "Barackness Monster." I don't know about you, but my life has been made.

2. Between Two Ferns

Zach Galifianakis is the king of aggravating deadpan humor that makes you want to simultaneously shake him and hug him. He is the best. But when he interviewed the president on his web series, Between Two Ferns, in March he essentially broke our brains. It was just too good.

Galifianakis starts out by telling the president, before the interview even begins, "Sorry I had to cancel a few times. My mouse pad broke last week and I had to get my great aunt some diabetes shoes." He then shushes Obama when he tries to respond.

Obama holds his own though and when Galifianakis later says, "It must kind of stink though that you can't run three times," Obama fires back:

If I ran [for President] a third time, it would be sort of like doing a third Hangover movie. Didn’t work out so well, did it?

Snap! And then Obama twists the knife by gushing over Bradley Cooper, Galifianakis' ultimate sore spot. You can watch the entire segment here.

1. The 2014 White House Correspondents' Dinner

Time and again, President Obama proves that he's not afraid to make fun of himself or his policies. At this year's White House Correspondents' Dinner, he joked:

Of course, we rolled out HealthCare.gov. That could've gone better. In 2008 my slogan was "Yes, We Can." In 2013, my slogan was "Control, Alt, Delete."

He also took the opportunity to jab at the other side, and at Congress, who made it really easy to make fun of them after 2013.

One thing we've been unable to agree on is unemployment insurance. Republicans refuse to extend it. I'm beginning to think they have a point. If you want to get paid while not working, you should have to run for Congress just like everybody else.

But perhaps his most chuckle-worthy jokes are the ones that have to do with John Boehner. That goes for anyone and any situation in life, by the way.

I'm feeling sorry, believe it or not, for the speaker of the House, as well. These days the House Republicans give John Boehner a harder time than they do me. Which means orange really is the new black.

I'm still wiping away my laugh-tears.