Who’s Next: Will Stephen

The Saturday Night Live writer brings a fresh perspective to the famed variety show.

Before joining “Saturday Night Live” as a writer three years ago, would put his name in the audience lottery like the rest of us, trying and failing time and again. Little did he know he’d one day be writing content for the show he’d revered since childhood.

“The thing that made me get into comedy is my parents buying me ‘The Best of Dana Carvey’ on VHS because they really liked his George H.W. Bush impression,” Stephen, 29, recalls. The District native, who was only nine or ten at the time, started watching SNL religiously, admiring the talents of its stars, including Tina Fey, Amy Poehler and Fred Armisen.

Educated at St.Albans School and Yale University, the brainy wordsmith studied both theater and literature. At Yale he joined the improv group Just Add Water, performing alongside actors like Allison Williams, who remains a close friend. With dreams to stay in comedy, Stephen moved to New York after college and took classes at the Upright Citizens Brigade while working a day job as an assistant to a theater professor. Some humorous articles for New York Magazine (including one where he dressed up to resemble Jared Leto and observed peoples’ reactions) grabbed the attention of College Humor, which hired him as their politics editor during the 2012 election.

Stephen says his big break came when he was asked to give a TED Talk. Suffering from writer’s block with nothing on paper just days before the show, he decided to spin his anxiety into humor, producing a piece about how he had nothing to say. The satirical bit, “How to sound smart in your TED Talk” got him an audition at Montreal’s Just for Laughs festival followed by SNL where he first auditioned as a performer but was hired as a writer.

“They like to hire people who have a performer’s sensibility, who know what it’s like to perform and what works and what doesn’t,” he explains.

Stephen clearly knows what works. He found a way to bring his two passions, “rap and politics” to some of SNL’s most memorable skits in recent years. Who can forget the Emmy Award nominated “Come Back Barack” in which Chance the Rapper begs the President to return, in the form of a ’90s R&B inspired music video. And “Drake’s Beef ” in which the rapper makes fun of his sensitive persona, lashing out musically with diss tracks at SNL cast members for perceived slights.

And in 2017, “Saturday Night Live” had its most-watched season in 23 years — thanks to the writers and performers who turned Donald Trump’s presidency into comedy gold.

“Everyone assumes that it’s easier to come up with material because Trump is so ridiculous but that actually makes it harder because you can’t just make the obvious joke. You have to be a little thoughtful,” Stephen says. As far as off-limits jokes, he notes that it’s the target of the joke that matters. “You don’t want to punch down. Don’t be a bully.”

Stephen, who shares an office with performer Alex Moffet, says his colleagues are what make the infamous all-night weekly writing sessions not only bearable but fun. “Kate and Kenan and Chris Redd are the funniest people in the world.” The close-knit team writes 40 to 45 sketches on Tuesday night, which get narrowed down to seven or eight for the live show, during a table read with the host and Lorne Michaels on Wednesdays. The table reads, Stephen says, are “the most nerve-wracking part of my job, because you’ve stayed up until 8 a.m. writing and all of a sudden have Tina Fey or Larry David reading it and you’re thinking, ‘Oh my God, I hope it works.’”

“It’s a crazy place,” he adds. “I feel like I’m going to spend the rest of my life unpacking all of the things I’ve experienced there because it just moves a mile a minute.”

This story appears in the September 2018 issue of Washington Life.

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