Ten years ago, before Anthony Jeselnik was among the best stand-up comics in the country, he was a monologue writer for Late Night with Jimmy Fallon. In those days, most of the jokes he pitched were deemed too dark for the sunny host.
“They didn’t really want my sensibility,” Jeselnik says on this week’s episode of The Last Laugh podcast. He ended up staying for a year and leaving of his own volition. He was long gone by the time Fallon ruffled Donald Trump’s hair on The Tonight Show and subsequently got blamed for “normalizing” the candidate just a few weeks before the 2016 election.
“I felt a little bad for Jimmy in that situation,” Jeselnik admits. But he doesn’t blame Fallon.
“Trump and Lorne Michaels are friends. And Lorne Michaels produced that show,” Jeselnik says of The Tonight Show. “And I’m sure—and I don’t want to put words in his mouth, and I haven’t talked to Jimmy in years—but I’m sure it’s one of his biggest regrets.”
In an interview last year, Fallon said that he never intended to “normalize” Trump and felt “depressed” amidst all of the backlash. “I made a mistake,” he added. “I'm sorry if I made anyone mad. And, looking back, I would do it differently.”
Fallon likely did not think Trump would go on to win the election when he had him on his show. And Jeselnik felt the same way in the fall of 2016. He was even pitching a show at the time based on the premise that with Hillary Clinton as president he could portray a villainous Trump-esque pundit in opposition to her, similar to the role Stephen Colbert ended up playing on The Colbert Report under President Obama.
“It seemed insane that he could win. I just didn’t believe that Americans would vote for him,” Jeselnik says. “But then you look back and you’re like, it wasn’t that surprising.” When he hears that “only” 40 percent of people approve of Trump, he imagines that another 20 percent say they don’t like the president but then will go out and vote for him anyway.
“But Jimmy’s not a political guy and I think he took a beating that he shouldn’t have taken,” he says. “Trump didn’t win the election because Jimmy ruffled his hair. It may not have been a great look for Jimmy, but it didn’t turn anything.”
He does not feel the same way about the man who produces both Fallon’s show and Saturday Night Live.
“I think Lorne Michaels helped get Trump elected,” Jeselnik declares, unequivocally. “I think putting him on SNL was way worse than the hair-ruffling thing.”
In November of 2015, months after he announced his candidacy by calling Mexican immigrants “rapists,” Donald Trump landed the coveted show business gig of hosting SNL—for the second time. At the time, and even more so in retrospect, it was an embarrassing night for the iconic show and only helped elevate Trump’s celebrity status.
“I was disgusted by it,” Jeselnik says. “It was two rich guys helping each other out. I don’t know how I would have dealt with it if I was on the show. I found it to be, quite frankly, revolting.”
Jeselnik came close to being behind the “Weekend Update” desk that night. Before the show’s 40th season started the previous fall, Michaels held auditions to replace Cecily Strong, who had been co-anchoring “Update” with Colin Jost. As Jeselnik explains it, they tried out about 10 different comics paired with Jost but he actually auditioned by himself.
“It wasn’t going to be me and Jost together,” Jeselnik says, positing that the show “didn’t want two white guys sitting there next to each other.” Plus, he adds, “I work better by myself.” His friend and fellow stand-up comic Michael Che ended up getting the position and still has it to this day.
“That was the one job I’ve ever wanted in my life,” Jeselnik says of the SNL gig that has often gone to accomplished stand-ups. “I’ve certainly moved past it now. And even at the time I thought my chance to do it was over.”
He says his best chance was probably when Seth Meyers left in the spring of 2014, but at that time he was hosting another show for Comedy Central and wasn’t available. When he did get the call that fall, he thought, “I’m not going to get this but it’s fun to have the audition and I’m not going to mess it up. If I don’t get this, it’s not going to be my fault.”
“When you go in, you’re in a suit, you’re on the set, you’re sitting behind the desk,” he says, “and the camera comes down and you hear the announcer say, ‘Welcome to Weekend Update with Anthony Jeselnik’ and I just started laughing.” Instead of a cheering crowd, there are a handful of producers sitting silently in the audience. He explains that it’s “set up for you to not do well” but he “killed it” anyway.
Despite the infamous stories from cast members who say that Lorne Michaels never actually told them directly that they were hired or fired, Jeselnik got a personal call from the producer. “Lorne actually called me himself to say, you did a great job but we’re going in this direction,” he says. “And I couldn’t argue with him. It’s his show. Looking back on it now, I’m glad I didn’t get it.” He says that former SNL writer John Mulaney told him, “You think you wanted that job,” but that he “would have hated” Michaels telling him what jokes he could and couldn’t tell.
Even more offensive to Jeselnik are reports from former cast members like Taran Killam that Michaels instructed writers not to “vilify” Trump in sketches when he was the host, telling them, “you have to find a way in that makes him likable.”
“I don’t know if would have shown up for work that day,” Jeselnik says. “I don’t know what would have happened.”