15 Times President Obama Was Completely Hilarious

As numerous watchers have noted over the last year or so, President Obama is clean out of fucks to give. He has entered the final leg of a presidency that has included dealing with a contentious do-nothing Congress, a nutty GOP and its lunatic base, and the standard age-advancing issues that come with the office (at least he signed up for that last one). Yes, every politician approaching a term limit is freer to pursue politically sensitive policies and to speak with greater candor and openness. But in Obama’s case, this period seems particularly well deserved.

Though the last few months have seen the president’s increasing willingness to call out—and even lightly mock—craziness when he sees it, Obama has always been a man who recognizes the value of a good joke. Whether cracking wise himself or aligning with famous comedians to advance his most treasured policies, the president has relied on humor throughout his time in office. The end of 2015 seems as good a time as any to look back at 15 particular instances when Obama employed comedy as a tactical device. 

1. The time he went on "Comedians In Cars Getting Coffee" with Jerry Seinfeld.

There are several great episodes of this webseries that features host Jerry Seinfeld tooling around with his comedian guest in a sporty vintage car, stopping for coffee and shooting the breeze. But this may be one of the surprise best. Obama, who shows Seinfeld his own cool ride, talks about his favorite presidents, the usefulness of swear words and how batshit crazy a fair amount of world leaders are. A genuinely enjoyable watch.

2. The time he snarkily told Republicans, “I know, because I won both of them."

When, during the State of the Union, Republicans burst into sarcastic applause when Obama stated he had “no more campaigns to run,” the president clapped back with a zinger that brought Dem members of Congress to their feet.

3. The time it was Obama vs. a fly.

Remember that scene in "Karate Kid Part 2" when Mr. Miyagi caught a fly with chopsticks? This was kind of like that.

4. The time he went on "Between Two Ferns with Zach Galifianakis."

From the chyron that identified him solely as a “community organizer” to being asked, “Where are you planning on building your presidential library, in Hawaii or your home country of Kenya?” Obama was a good sport on Zach Galifianakis’ consistently great webseries. The president landed a few barbs of his own, including responding to Galifianakis’ suggestion that he’d like to run again by quipping, “If I ran a third time, it’d be sort of like doing a third 'Hangover' movie. Didn’t really work out very well, did it?” The whole thing was a pretty smart strategy for the president to reach young people about enrolling in the Affordable Care Act.


5. The time he let a Fox reporter know how dumb his question was by repeating it back to him.

In the midst of a March 2012 press conference, Fox News correspondent Ed Henry suggested the president, who was then running for his second term, wanted the price of gas to keep rising.

“Ed, just from a political perspective, do you think the president of the United States going into reelection wants gas prices to go up higher?” Obama asked the entire room. “Is there anybody here who thinks that makes a lot of sense?”


6. The time he let his anger translator speak for him.

For five seasons, Comedy Central’s brilliant "Key & Peele" has featured a recurring sketch in which Luther, the president’s “anger translator,” says what our unflappably cool president actually means. At this year’s White House Correspondents Dinner, Obama brought an in-character Keegan Michael-Key onstage and played the straight man while Luther channeled his rage out loud. 

7. The time he compared Republicans to Grumpy Cat.
Speaking at the Democratic National Committee’s Women’s Leadership Forum, Obama took a moment to note that Republicans are awful “gloomy” and “down on America.” “They’re like Grumpy Cat,” the president stated, and then did a fairly perfect sad-faced impersonation of both the actual Internet-famous feline and the entire GOP.
8. The time he did the Buzzfeed selfie stick video.
Conservative heads exploded when Obama appeared in this Buzzfeed video clip, titled “Things Everyone Does But Doesn’t Talk About.” You can’t blame the guy for understanding the medium of choice for the demographic he was trying to reach (again, to sign up for the ACA). Choice moments include Obama trying his hand with a selfie stick, practicing being presidential in the mirror, and muttering, “Thanks, Obama!” as a catchall complaint.
9. The time he pretended to be Daniel Day-Lewis...as Obama.

In this brief mockumentary from the 2013 White House Correspondents Dinner, Steven Spielberg does a rare turn in front of the camera as himself, pretending he's planning to follow up 2012’s Lincoln with the biopic of another president: Obama. President Barack Obama stars as Daniel Day-Lewis starring as President Barack Obama, if that makes any sense. There’s also a cameo by Tracy Morgan, describing his role as, of course, Vice President Joe Biden.

10. The time he made fun of both Donald Trump and Fox News’ birtherism (while wearing a tux).
Back in 2011, instead of being the crown prince of the Republican party, Donald Trump was just a loudmouth reality TV star with a trust fund and a string of bankruptcies. He was also an attention-seeking birther, one crazy among the many the president was tacitly addressing when he publicly released his long-form birth certificate. At the White House Correspondents Dinner that year, Obama took things a step further by releasing his “official birth video” (actually, a clip from The Lion King), made fun of Fox News for potentially taking it seriously, and made a few well-deserved jokes at The Donald’s expense.
11. The time he made fun of a heckler.
By his second term, President Obama—a man right-wing nutters have alternately labeled a terrorist, a Kenyan, a Communist and/or the Antichrist—was pretty at home having ridiculous conspiracies thrown at him. In 2014, during a speech at the Democratic National Committee, a distant voice could be heard shouting, “Mr. Obama, tell us about your plan for nuclear war with Russia!” Instead of ignoring it, Obama challenged the heckler head-on, asking incredulously, “What the heck are you talking about?” He drew out the whole thing for extra laughs before smoothly picking up where he’d left off.
12. The time he took over "The Colbert Report."
Appearing on the now defunct "Colbert Report," Obama took over the host’s desk and proceeded to present “The Wørd” segment. (For just this presidential instance, it’s called “The Decree.”) Ever the media-savvy Commander-in-Chief, Obama made fun of himself even while promoting his healthcare agenda. He makes bigger fun, though, of Republicans and their endless attempts to overturn the ACA.
13. The time he did "Slow Jam the News" with Jimmy Fallon.
President Obama joined "Tonight Show" host Jimmy Fallon during a segment of the recurring "Slow Jam the News" segment, which entailed the two discussing the news over a quiet storm provided by The Roots. In this set-up, Obama talks his appeal to Congress to keep Stafford student loan rates from increasing, as part of what is very likely the only slow jam ever written on the subject.
14. The time he read mean tweets about himself on Jimmy Kimmel.
If there is a gem of a gift Jimmy Kimmel can be credited with giving the world, it is showing us how funny it is when famous people read mean tweets about themselves. Earlier this year, the president dropped in for a "Mean Tweets" segment of all anti-Obama messages. It’s not the first time someone on social media made fun of his jeans, and it won’t likely be the last.
15. The time he went on "WTF with Marc Maron."
Marc Maron has gone from being an obscure standup who interviews his comedian friends in his garage, to a guy who has one of the most important podcasts—and press stops—out there. This is perhaps one of the most frank conversations a sitting president can have, with Obama touching on issues from gun control to racism to the comedians who inspired him (Richard Pryor, Dick Gregory, Jerry Seinfeld and Louis CK). In case you’re interested, Maron did a followup episode reflecting on his encounter with the president called "The President Was Here."
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