The Best Shots-Fired Moment
Janie Stolar, writer and performer at the Upright Citizens Brigade Theatre
Twitter Handle: @janiefierce
How It Went Down: At the 2016 White House Correspondents' Dinner, Obama let his feelings about his successor be known: "And there's one area where Donald's experience could be invaluable, and that's closing Guantanamo, because Trump knows a thing or two about running waterfront properties into the ground."
Why It's Great: "During an election race when everyone seemed terrified to call out Trump for what he was, Obama did it, and pointedly so," Stolar says. "Obama was always willing to bring up the important issues plaguing his own presidency too; he always seems to remain down to earth."
The Best Pop-Culture Dig
Rekha Shankar, comedy writer for MTVNews and Reductress
Twitter Handle: @rekhalshankar
How It Went Down: In 2014, Obama went on Zach Galifianakis's cult web series Between Two Ferns, becoming the show's most famous guest and, arguably, one of its snarkiest: "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?"
Why It's Great: "This was amazing, because I did not like the Hangover movies," says Shankar. "I'm sorry! They were so dude-heavy and fratty, and they do literally everything they tell you not to do in a well-written scene—they keep talking about things that already happened instead of really doing things, and the whole movie is about substance use and partying. As a female comedian, I find that no one in the country can really put fratty white bros telling bro-y frat jokes in their place... except the g.d. president of the United States. BAM! Barack 'n' roll."
The Best Joke About a Turkey
Austin Rodrigues, contributor to Funny or Die, writer and performer for the Upright Citizens Brigade
Twitter Handle: @austinnewyork
How It Went Down: Every year before Thanksgiving, Obama pardons one turkey, preventing it from becoming dinner. This was his final turkey pardon, on November 23, 2016: "I want to take a moment to recognize the brave turkeys who weren't so lucky, who didn't get to ride the gravy train to freedom, who met their fate with courage and sacrifice, and proved that they weren't chicken."
Why It's Great: "I love puns," Rodrigues says. "We all secretly love puns. Puns get a bad name, but if anyone can make them cool, it's Obama. In his final turkey pardon speech last year, the president really set the good pun standard."
The Best Make-a-Girl-Blush Moment
Matthew Starr, writer and performer at the Upright Citizens Brigade
Twitter Handle: @matthewsstarr
How It Went Down: "In this clip," Starr says, "a man passes by President Obama while he's casting his vote during the 2014 midterm elections, and says, 'Mr. President, don't touch my girlfriend.' With his response, President Obama amazes me with his innate sense of humor and his effortless style.
Why It's Great: "He labels what he finds funny," Starr says. "He disarms and charms the guy like they're friends. He has fun embarrassing the girlfriend further, while still being on her side and making her laugh. He's so self-aware in the best way. And then he takes the joke and owns it by giving the girl a kiss. Everyone walks away with their dignity, and President Obama has the last laugh. Wow."