Jon Stewart Is Solving the Problem (Or at Least, He’s Trying To)

Jon Stewart is mid-earnest-monologue, talking on the phone and walking out of his New Jersey home and into his car, where he’ll head to New York to tape his Apple TV+ show The Problem With Jon Stewart. “At some point, the car phone will pick up and I’ll lose you,” he warns. “Probably at a very profound moment where I’m delivering—I don’t want to say a pearl of wisdom, necessarily, but certainly a jewel.”

Defying all odds, the car phone picks up smoothly enough, and Stewart dives back into his stream of profundity, in which he is candidly addressing the kinks in the Emmy-nominated first season of The Problem, his late-night series about current affairs, which returns for a second season this Friday. “One of the hardest things to do is take an objective look,” he says. “A postmortem. Trust your discomfort when you’re seeing things that aren’t working or feel a little off.”

He continues, appraising the early episodes of the show. “In the first season, my interviewing was a little less directed and not as focused. I think that made it much harder to be clear to the audience,” he continues. “It made it too meandering. It really was about pruning, taking out things that weren’t essential that muddled the point of view. How do we weed this garden and get it a little cleaner? I think season two is more successful in that regard.”

The first two episodes of season two present a sharper, more refined version of the show, shaving off the more casual segments of the freshman effort, like sneak peeks into the writers room. But the overall vision remains intact. The show still opens with Stewart behind a desk (this season, in a suit), firing off jokes about the day’s chosen topic, or “problem,” leading into montages culminating in the essence of the thing. Stewart conducts group interviews with a variety of guests, then segues into a pretaped interview with an expert or political foe. 

The first episode, for example, focuses on gender, and Stewart conducts a razor-sharp sit-down with Arkansas attorney general Leslie Rutledge, who was defending her state’s ban on transgender children receiving gender-affirming medical care. The interview is a thrill to watch. Stewart is in classic form, simultaneously funny and unflinching as he lets the attorney general fall on her own sword. His questioning reveals that she is shockingly light on “facts” to back up the legislation. (The law has been blocked, most recently by a federal appeals court, in August, when Rutledge said she planned to ask the court to review its decision.) She eventually pushes back on Stewart by saying she “wasn’t prepared to have a Supreme Court argument today.”

“I was like, You’re the attorney general,” Stewart tells VF. “Whether you’re defending it to the Supreme Court or a bartender, what’s the difference? Surely you have something to back this up.”

Speaking of political foes, each episode of season two ends with a new bit: A clip of Republican Senator Ted Cruz, titled the “Moment of Cruz.” The idea was inspired by “our special relationship,” Stewart jokes of the highly conservative, highly unpopular senator, whose career has been riddled with gaffes, controversies, and gross political stances. “It’s a play on where I used to live and my experience down in DC, where he was a remarkable foil.”

It’s also, of course, a nod to the “Moment of Zen” segment from Stewart’s run on The Daily Show, where he ended each episode smiling beatifically as a soothing clip played. He’s far removed from his brutally paced days on The Daily Show, which he hosted from 1999 to 2015. After leaving, he passed the mantle to Trevor Noah, who recently announced that he was stepping down after seven years on the job. Stewart is supportive of Noah’s decision, all too aware of how tough the show is to maintain, especially if you have ambitions to work on different kinds of projects. “If you want to do it to its highest excellence, which I think Trevor did, it’s a sole focus,” he says. “He’s an incredibly creative and varied performer. Going on the road, producing, writing, all those things—there’s no way you could achieve both and have them live up to the standards that I’m sure he sets for himself.”