(Michael Arnold/For The Washington Post)

Is there a more perfect expression of the First Amendment than roasting the head of state?

Comedy greatly shapes the public’s perception of a president. Recall Will Ferrell’s “Saturday Night Live” impersonation of George W. Bush, which arguably made the president more likable — a lovable buffoon who, sure, couldn’t say “strategy” but would indeed be so fun to share beers with.

For comedians, President Obama presented a unique challenge. Here was the first black president, whose very existence evoked earnest desires of hope and change. He is friends with Jay Z and Beyoncé. He lacked the personal scandals or catchphrases that easily opened him up to ridicule (wearing dad jeans and coming across as aloof can only go so far, comedy-wise). And pop culture tends to lean liberal; many comedians clearly liked the man.

“He’s just one of those guys, you know,” Chris Rock explained in 2009, “There’s no Brad Pitt jokes. You know, what are you going to say? ‘Oh, you used to have sex with Jennifer Aniston. Now you have sex with Angelina Jolie. You’re such a loser.’ . . . [With Obama] It’s like, ‘Oh, you’re young and virile and you’ve got a beautiful wife and kids. You’re the first African American president.’ You know, what do you say?”

Obama himself used a lot of humor to deliver his messages, and because he was the first social media president, he didn’t have to go on a late-night show to be funny. He could just do it in a Facebook video. And, in the process, he shaped his own comedic persona.

But the comedy world sure did try to make fun of Obama. How did it do? Here’s a look back at the highlights:

Fred Armisen plays Obama on ‘Saturday Night Live’ (February-2008)

During the primary season, Armisen — who is of Japanese, German and Venezuelan ancestry — wore darkening makeup as he impersonated the then-senator. The debut sketch lampooned glowing media coverage of Obama compared with that of opponent Hillary Clinton.

While SNL cast members have impersonated people of races different from their own, the choice of a nonblack comedian to play Obama became especially controversial given the possibility of the nation electing its first black president. In defending the casting, SNL executive producer Lorne Michaels told The Washington Post, “When it came down to it, I went with the person with the cleanest comedy ‘take’ on” Obama.

Armisen’s impersonation was deadpan, including some of Obama’s mannerisms but relying heavily on the written material. Over the years, he combined Obama with other characters, such as a stand-up comic and Cliff Huxtable.

“Black Man Given Nation’s Worst Job” — The Onion, November 2008

‘Thanks, Obama’ meme (September 2009)

Opponents of the president and his agenda first used this phrase as a sarcastic way to criticize him. One of the tweets came in September; three months later, it appeared on inverted motivational posters, giving birth to a meme. One tweet: “13,039,659,204,693 <<< Current National Debt! #thanksobama.”

In 2011, liberals hijacked #ThanksObama and used it ironically to mock conservatives’ use of the phrase. Entire sites were dedicated to collecting GIFs and edited images of Obama with phrases like, “I left my sunroof open and it rained. Thanks, Obama!” The meme jumped the shark when Obama used it in a February 2015 BuzzFeed video.

First Lady Michelle Obama, President Barack Obama and comedienne Cecily Strong of the Saturday Night Live show chat during the annual White House Correspondent's Association Gala at the Washington Hilton hotel in 2015. (Olivier Douliery-Pool/Getty Images)

White House Correspondents’ Association dinner performances (2009-2016)

Obama generally did well at these dinners, sometimes overshadowing the headlining comic. One his favorite targets was “the birthers,” which he alluded to nearly every year. For instance, when talking about dropping approval ratings in 2010, Obama said: “But that’s politics. It doesn’t bother me. Besides, I happen to know that my approval ratings are still very high in the country of my birth.”

“President Obama was in India yesterday visiting our jobs. Tomorrow he goes to China to visit our money.” — Jay Leno, “The Tonight Show,” November 2010

Luther the Anger Translator (January 2012)

This recurring sketch on the Comedy Central series “Key and Peele” portrays Obama (Jordan Peele) as cool and collected, while Luther (Keegan-Michael Key) says what’s really on the president’s mind. After a seated Obama calmly states a position, Luther explodes, yelling at the camera, bouncing around and using profanity.

In real-life, Obama “couldn’t come off like an angry black man, especially early on, so what Luther says are things that ring true to us,” Peele explained in 2013.

Keegan-Michael Key, left, and Jordan Peele. (Ian White/Comedy Central)

The concept reached a new zenith when the show released a wildly popular victory sketch online immediately after Obama won reelection.

“Thank you for your support,” Peele, as Obama, said. Luther’s translation: “You know how much money they tried to spend to get rid of me?! Millions, son! I said, millions!”

“Hey, Mr. President, do you remember when the country rallied around you in hopes for a better tomorrow? That was hilarious.” Jimmy Kimmel at the White House correspondents dinner, April 2012

SNL Obama switches to Jay Pharoah (September 2012)

“Saturday Night Live gives job of playing Barack Obama to actual black man,” was how the A.V. Club put it. Pharoah’s take on Obama is much closer to the man himself, including exaggerated mannerisms, a scrunched up face and frequent pauses.

“I learned a lot in my first term that I’m ready to apply to my second,” Pharaoh, as Obama, said in a November 2012 appearance. “Mainly, that this is a terrible job, and I hate it.”

Obama mulling military intervention into Syria, as told by the Onion (2013)

Obama faced mounting pressure as to whether the United States should intervene militarily in the Syrian conflict, particularly after evidence showed chemical weapons were used there. The president’s critics accused him of flip-flopping, being indecisive or lacking a real plan.

Pretty heavy stuff. But the satirical Onion didn’t hold back and published articles throughout the year taking Obama to task. A sampling:

“ ‘Syrians’ Lives Are Worthless,’ Obama Tells Daughters Before Kissing Them Goodnight”

“Obama Deeply Concerned After Syrians Gassed To Death On White House Lawn”

“Obama Throws Up Right There During Syria Meeting”

“That’s what it feels like to be me. I work all my life to make some money and finally all my dreams start coming true and all of a sudden a black president comes out nowhere and goes, ‘Come on Dave, let’s be responsible.’ Oh n---- I just got this money! Come on, Barack! ‘Dave, come on. Think about everybody.’ ” — Dave Chappelle on Obama’s tax proposals, in a Web video posted in February 2013

Host Jon Stewart during a taping of "The Daily Show with John Stewart", in New York. (Carolyn Kaster/AP)

Affordable Care Act rollout (October 2013)

The botched rollout of Obamacare gave comedians perhaps their best opening yet to directly ridicule Obama. Take “The Daily Show” treatment: Jon Stewart played clips of Obama trying to sell the public on the online exchange, and then quipped, “When did the president of the United States turn into Gil from ‘The Simpsons’?” Cut to a clip of a desperate cartoon salesman selling outdated technology.

A new ‘Michelle Obama’
on SNL
(January 2014)

Sasheer Zamata. (Evan Agostini/Invision/AP)

Guest hosts like Maya Rudolph and Kerry Washington had played the first lady on SNL, but the show lacked a black female cast member who could do so. The cast’s demographics came under scrutiny after comments from Pharoah and Kenan Thompson, who said he would no longer perform as a woman.

So Michaels held a special audition. While he said needing someone to play the first lady wasn’t the only priority, all comedians were asked to do at least one Michelle Obama impersonation. Sasheer Zamata was cast in January 2014 and made her first appearance as Michelle that May.

President Obama, left, with actor-comedian Zach Galifianakis during an appearance on "Between Two Ferns." (Funny or Die/via AP)

‘Between Two Ferns’ (March 2014)

Obama appeared on “Between Two Ferns,” opposite Zach Galifianakis, to plug healthcare.gov. Per the concept of the popular Web series, host Galifianakis tries to taunt his guest. He asked Obama: “What is it like to be the last black president?” and “In 2013, you pardoned a turkey. What do you have planned for 2014?”

The president took on a mean persona of his own, and volleyed the barbs right back. “Was that depressing to you? Seeing that one turkey kinda taken out of circulation? A turkey you couldn’t eat?”

Stephen Colbert at the Kennedy Center Honors (December 2014)

Democrats had just lost the Senate the previous month after many politicians tried to distance themselves from Obama. So at the Kennedy Center Honors, Stephen Colbert pointed out the attendance of “the most powerful and influential person in the world, Michelle Obama. . . . There she is, looking radiant, on camera next to the president, which I assume means she has no future plans to run office. . . . There are a lot of Democrats who don’t have that courage.”

Cecily Strong at the White House correspondents’ dinner (April 2015)

“Even us at SNL got criticized for making fun of ISIS. Now I think that’s unfair. I mean, if anyone is guilty of taking ISIS too lightly, it’s him. [Gestures to Obama]”

Cuban President Raul Castro, right, lifts up the arm of President Barack Obama at the conclusion of their joint news conference in Havana, Cuba. (Ramon Espinosa/AP)

Obama’s historic Cuba visit (March 2016)

Obama and Cuban President Raúl Castro shook hands. It was hysterically weird.

“The two men shared the most awkward handshake in presidential history,” Seth Meyers said on his late-night show. “Look at Obama going rag-doll limp. That might be a puppet’s arm. That is the handshake of a man who does not want a photo taken.”

Larry Wilmore at the White House correspondents’ dinner (April 2016)

At the president’s last correspondents’ dinner, host Larry Wilmore ended the evening with a controversial closer: “Mr. President, if I’m going to keep it 100: Yo, Barry, you did it, my n----. You did it.”

But before that, Wilmore aimed some biting remarks at the president, including: “Saw you hanging out with NBA players like Steph Curry, Golden State Warriors. That was cool. You know, it kind of makes sense, too, because both of you like raining down bombs on people from long distances, right?”


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