President Barack Obama’s greatest comedy hits and a thank you for being our headliner-in-chief

I’m hoping I won’t bring Secret Service running if I say no one blows up the stage and kills with a mic like President Barack Obama. He deserves the title Honorary Comedian. He’s got the heart, the spirit, and certainly the timing and delivery which just got better and sharper and more confident over the past decade. The President is a triple threat, too. He does sketch, stand-up and improv. Here are my favorites:

(1) Saturday Night Live, Season 33 (2007)

An early example of President Obama’s perfect comedic delivery and timing.


(2) President Obama slow jams the news with Jimmy Fallon (2016)


(3) Comedians in Cars Getting Coffee (2016):

Unfortunately, not an embeddable link, but click to see President Obama outshine a 1963 silver blue Corvette Stingray. When a White House guard refuses to let Jerry Seinfeld take the President for a spin on Pennsylvania Avenue, they’re forced to circle the White House driveway and chat in the mansion’s basement cafeteria. But I’m not sure I even noticed the surroundings.

Favorite line not said by President Obama or Jerry Seinfeld:

White House Guard: You’re a comedian with a President going nowhere.”


(4) Between Two Ferns (2014)

With nearly 14.5 million YouTube views, this President Obama appearance was touted as a way to raise the Affordable Care Act’s profile with millennials. I just like to imagine President Obama writing this sketch into the early morning hours with Zach Galifianakis and director Scott Aukerman. In truth, in an interview with, Scott Aukerman said that the White House “got out of the [writers’] way,” but when asked what happens when the President pitches a joke he said, “I don’t think the president has to pitch jokes, he just says jokes and we enjoy them.” He went further in an interview with Adweek: “He really seemed to enjoy poking Zach. A lot of that was improv, and Obama came up with some really good lines.”


(5) State of the Union (2015)

President Obama improvised the line “I know because I won both of them” and got an applause break.


(6) White House Correspondents’ Dinner 2009


(7) White House Correspondents’ Dinner 2010


(8) White House Correspondents’ Dinner 2011

This dinner earned notoriety as the event that  allegedly goaded Donald Trump into running for President. True, host Seth Myers and President Obama made merciless fun of him, but Donald Trump at least publicly, insisted that he had a “great” and “phenomenal” time. Here is a Washington Post article cataloging the back and forth of whether this was decision time for Donald or not, including a video compilation of the sound bytes in question. I’m looking forward to anything and everything President Obama does in his post-presidential years to ensure DJT does not have the last laugh.



(9) White House Correspondents’ Dinner 2012

I know the President had assistance from speechwriters for these dinners, but reportedly he regularly tweaked the timing and wording.  I can’t think of any other president who delivered WHCD lines so well and so naturally. He turned the material from the rote punctuation of “set up/punch” into master sets.


(10) White House Correspondents’ Dinner 2013


(11) White House Correspondents’ Dinner (2014)


(12) White House Correspondents’ Dinner (2015)

The one with Official Anger Translator Luther! I marvel at President Obama’s ability to keep a straight face while Luther went ballistic behind him. Great demonstration of the pro’s ability to focus no matter the comedic mayhem breaking around him.  Keegan-Michael Key talks about the President’s comedic talent here. Local comedy alert!  Keegan-Michael Key and Jordan Peele met in Chicago.


(13) President Obama’s White House Correspondents’ Dinner (2016)

“Obama out.” Damn. Thank you, President Obama, for your integrity, compassion and brilliance on all fronts and for knowing how and when to be hilarious on top of all that. If I weren’t laughing, I’d be crying.


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