During his time in the White House, President Barack Obama proved more pop culture-savvy and casual then most - if not all - presidents before him. At 47, Obama was the fifth-youngest man to take the US' highest office in 2009. Pop culture references and humor were a signature part of the brand established by the president and his millennial-heavy staff, from self-deprecating dad jokes at the annual Turkey pardon to references to cult movie Mean Girls on Twitter. 

The (Lion) King of the Correspondents' Dinner

Obama, a skilled speaker with impeccable timing, often peppered his speeches with jokes. This came in handy at his eight White House Correspondents' Dinners. Every year since 1920, Washington journalists have hosted the gala, where the president is expected to give a humorous speech. While many presidents soldiered through this tradition amid polite chuckles, Obama, a seeming natural stand-up comedian, often had the room roaring with laughter.

He took his 2011 speech as an opportunity to hit back at Donald Trump, who had claimed that Obama was not born in the US and thus not eligible for the presidency. 

Four years later, Obama was joined on the stage by his "anger translator." Luther, played by actor Keegan-Michael Key, had long been a fan favorite on the popular sketch show "Key & Peele." Now, Key finally got to play the Id to real Obama's Ego, rather than the show's version of the president. 

Quick with a comeback

While Obama mainly performed jokes a young team of speechwriters (several of whom have since gone on to work in comedy) wrote for him at the Correspondents' Dinner, he often provided quips off the cuff in other situations, taunting political opponents with quick comebacks or diffusing tension and awkwardness with humor. When his presidential seal fell of his podium during a speech, he joked "That's alright, all of you know who I am." 

'Late Night Comedy President'

Obama was a frequent guest on late night talk shows, doing interviews with nearly all the prominent US hosts  - he was in fact the first sitting president to go on a late night show. "Fortune Magazine"  dubbed him the "Late Night Comedy President." Obama often talked to the hosts about more serious issues like the racial divide in the US, but he also joked about how his daughter taught him Snapchat.

In a fragmented media landscape, where many people turned away from traditional news outlets, Obama embraced comedy and entertainment as a platform to address his agenda. Obama "slow-jammed the news" with Jimmy Fallon and read mean tweets about himself for Jimmy Kimmel. 

Bringing edginess to presidential humor

Obama earned both praise and criticism for his embrace of edgier comedy and new media. In the "Washington Post" newspaper, Emily Heil called Obama "the first alt-comedy president," writing that "Obama’s style, comedy writers say, belongs to the alternative comedy subgenre - a style of humor that breaks with traditional stand-up, loosely defined by irony, self-awareness, and quirky topical references."

Many conservatives criticized Obama's appearance on "Between Two Ferns," a quirky online talk show parody hosted by comedian Zach Galifianakis, as "undignified."

Obama defended his decision to appear on the show, saying that it allowed him to raise awareness for his healthcare plan among young people. 

'Obama out'

When Obama hosted his last White House Correspondents' Dinner in April 2016, he ended his speech with the words "Obama Out" and a favorite in his pop-culture reference-heavy comedy tool kit: the mic drop.