Late night laughs

A pillow salesman isn't exactly synonymous with "political pundit," but in "A Closer Look," a popular segment on NBC's Late Night With Seth Meyers, it's regular comedy gold.

After a November 2022 video of My Pillow CEO Mike Lindell's frenzied rant blaming the deep state and China for Republican losses in midterm elections, Meyers quipped that Lindell would be the only guy cut off at Starbucks, the way a bartender cuts off a drunk.

"He's like McGruff [the Crime Dog] if someone put meth in his kibble," Meyers jokes, earning big laughs from the studio audience.

Off camera, the segment came together thanks to Sal Gentile, A&S '08, who has been with the show since 2014. Gentile is the architect of "A Closer Look," a fast-paced, joke-packed monologue that takes viewers through the latest headlines and viral political gaffes, with the goal of revealing larger messages about U.S. politics.

Gentile, who double majored in Writing Seminars and Philosophy, says his time at Johns Hopkins prepped him for his current gig. He joined the student-run Witness Theater, where participants were challenged to write one-act plays in just 24 hours. He calls "A Closer Look" a "24-hour theater experiment."

"I start writing a thing and Seth has to do it the next day, and it has a bunch of insane tangents and crazy characters and impressions," Gentile says.

The show, which is filmed at 30 Rockefeller Plaza in New York City, places Gentile in the same building as programs he admired growing up, including Saturday Night Live and Late Night With Conan O'Brien. It may be hard to believe that a guy who has racked up seven Emmy nominations for writing and producing once thought a career in comedy unattainable. After college, the News-Letter alum turned to journalism because the news seemed like "the most responsible way of turning writing into a career."

Gentile first worked as an online writer and production assistant at WNET, a New York City metro-area PBS station. When his now wife, Jackie Jennings, A&S '08 began taking improv classes at the Upright Citizens Brigade Theatre in New York City in 2008, he realized that he still had an itch for theater. He soon followed, taking sketch and improv classes from the program where comedians like Amy Poehler and Aziz Ansari cut their teeth.

"I loved improv in particular because it feels like writing on your feet," Gentile says. "You're thinking of what the next funny move could be in a scene. And you're organically creating something with a bunch of other people, which is like re-creating a writers' room but on a stage."

By 2012, Gentile's day job was as a segment producer for MSNBC, writing scripts for Up With Chris Hayes, a weekend morning show. Then came a chance meeting in the hallways of 30 Rock in 2013. Wearing his UCB sweatshirt, Gentile ran into Mike Shoemaker, a writer and producer for the newly announced Late Night With Seth Meyers. Shoemaker recognized the logo and chatted him up, letting Gentile know that Meyers needed a segment producer with political and comedic experience. Gentile got the job. The show premiered in 2014, and as the 2015 presidential primaries heated up, he was tasked with writing deft pieces about politics and news. Melding his MSNBC and comedy experiences, Gentile began pitching political stories and jokes that underpinned what ultimately became "A Closer Look."

Now, the segment thrives on a collaborative process that begins with finding the most important stories and mining them for comedic potential. "We try to start with a broader thesis that connects a bunch of stories and explains them in a way that ties the narrative thread together," Gentile says.

His scripts start as 25 to 35 pages of jokes, punch lines, and ideas for news clips he may need. Then Meyers and other staff whittle it down. The script evolves through cue card writing to last minute changes just before showtime at 4 p.m.

With controversies in all three branches of government making Americans news-weary, the segments are just as cathartic for audience members as they are for Gentile. "We live in this era of distorted reality and we're just trying to put our feet on the ground and reaffirm what's true and use our sense of comedy as a natural BS detector," Gentile said.

With 24-hour breaking news, Gentile has had to abandon entire scripts and start from scratch. Like the day in 2018 when Rudy Giuliani admitted in a Fox News interview that former President Donald Trump had funneled hush money through a law firm to adult film star Stormy Daniels to evade campaign finance laws.

"I had already written 'A Closer Look' about something completely unrelated," Gentile said. "So that was one of those nights where I took a 30-page [script] and dropped it in the wastebasket."

With the 2024 presidential election around the corner, Gentile says that planning for the political news environment is like "putting a rake right in front of yourself to step on."

What isn't clear is how soon Gentile will be able to continue poking fun at it all. In May, Gentile was among the writers who writers put down their pencils and picked up picket signs when their union, the Writers Guild of America, went on strike. The Alliance of Motion Picture and Television Producers, which represents film and TV studios, rejected the guild's proposals for raising writer pay and limiting the use of artificial intelligence in the creation of film and television, among other contractual revisions.

Gentile misses the writing of "A Closer Look" but admits that the solidarity on the picket line motivates him to go as long as it takes to ensure that writers make a livable wage. But he already knows the first thing he's going to do once the strike is over.

"I'm going to write a Dostoevski-length 'A Closer Look' that we will publish as a hard cover," Gentile jokes.