'Awards Chatter' Podcast — Jimmy Fallon ('The Tonight Show Starring Jimmy Fallon')

Andrew Lipovsky/NBC

"I did not do it to 'normalize' him or to say I believe in his political beliefs or any of that stuff," says Jimmy Fallon at the point, during our recording of an episode of The Hollywood Reporter's 'Awards Chatter' podcast, when our conversation inevitably arrives at the Sept. 15, 2016, episode of The Tonight Show. That evening, with late night's most iconic program sitting atop the 11:30 p.m. ratings, Fallon welcomed as his guest Donald Trump, whom Fallon had previously interviewed seven times on his first NBC late-night show, Late Night, during the Apprentice era, and then taped a sketch with a year before on The Tonight Show, when Trump was a long-shot candidate for the Republican presidential nomination. Now, though, Trump was the nominee — albeit one given no real chance of defeating Hillary Clinton — and Fallon, as jovial an on-screen presence as anyone who has ever held a late-night job, tossed him some softball questions and then asked for — and was granted — permission to "mess up" Trump's hair, which long had been the subject of speculation and derision.

It was, it turned out, the biggest mistake of Fallon's career. He almost immediately began taking incoming fire on social media from people who felt that Trump was an existential threat to America whom Fallon had 'normalized' for people who were still on the fence about him. "It just got bigger and out of control," Fallon recalls, speaking in his office at 30 Rock. Then came the shots from Fallon's colleagues. "I saw other comedians from other shows making fun of me on Twitter and I go, 'Okay, now I'm just gonna get off,'" he says. "They know the show. I'm just doing five hours a week. I get in at 10 in the morning, I work 'til seven at night and I'm just trying to make a funny show. [Addressing them:] 'You know the grind and you know me. Of all the people in the world, I'm one of the good people — I mean, really. You don't even know what you're talking about if you say that I'm evil or whatever.' But people just jump on the train, and some people don't even want to hear anything else. They're like, 'No, you did that!' You go, 'Well, just calm down and just look at the whole thing and actually see my body of work.'"

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Fallon was born in Brooklyn and raised in upstate New York. The younger of two children of an IBM employee and a homemaker, he was, as one might assume, a cutup at home and a class clown at school, and developed a fascination with the mechanics of comedy from an early age. He begged his parents to let him stay up late enough to hear the monologue on Johnny Carson's version of The Tonight Show, and he convinced them to provide him with videotapes of Saturday Night Live episodes (which they censored to make them kid-friendly). For a time, it looked like Fallon, an altar boy who attended Catholic schools, might be headed towards the priesthood — "I was really into it, I loved it," he says of life in the church — but in 1992, shortly after graduating high school, he entered, at the encouragement of his mother, a talent contest seeking the funniest person in the Hudson Valley. He performed a bunch of his celebrity impersonations and prevailed, taking home $700, which convinced him to continue to hone his material even as he headed off to Albany's College of Saint Rose. A semester before he was to graduate, Fallon's friend got a tape of his work into the hands of a Brillstein-Grey Entertainment manager, who offered to represent him and urged him to relocate to Los Angeles. His parents blessed the move — after first making him take and pass the test to become a mailman so he would have a fallback career if his dreams out west didn't pan out.

It wasn't immediately clear that they would. For a while, Fallon was sleeping on friends' couches, subsisting on ramen noodles and barely making ends meet through occasional sets at The Improv, while also taking classes at The Groundlings. He eventually was hired to act in an indie movie and a TV pilot, but insisted on a contractual clause that would set him free were he ever to get an opportunity to realize his greatest dream, namely, working at SNL. Sure enough, his manager was able to secure him an audition in front of Lorne Michaels when Michaels was out in L.A., but Fallon tanked — "It couldn't have been worse," he emphasizes — and Tracy Morgan got the job instead. A year later, though, ahead of the show's 24th season, Fallon was offered another shot, this time at the show's fabled Studio 8H at 30 Rock, and he arrived better prepared — and even managed to crack up the famously stone-faced Michaels. He was invited to join the show's cast and, for six seasons — the latter three of which he spent co-anchoring "Weekend Update" with Tina Fey — was one of its most prolific and popular members. When he eventually left the show to try to pursue a film career, Michaels planted an idea in his head: that Fallon might one day return to 30 Rock six years hence, when Late Night host Conan O'Brien was slated to replace Jay Leno as the host of The Tonight Show, to become the new host of Late Night.

Six years later, Fallon — whose movie star aspirations had been dashed by the critical and commercial failures of 2004's Taxi and 2005's Fever Pitch — was again approached by Michaels about that possibility. After consulting with his wife Nancy Juvonen, a producer whom he met on Fever Pitch and married in 2007, he decided he could not turn down the opportunity to follow in the footsteps of not only O'Brien, but also David Letterman before him. NBC executives initially pushed back against Michaels' idea, but they wanted Michaels to serve as the show's executive producer, and Michaels refused to do so unless Fallon was made the host. "That's a big person going to bat for you," Fallon marvels. "I really never forgot that." During the four years that Fallon anchored Late Night, spanning 2009-2013, he crafted the same sort of show that he continues to put on to this day: a light one centered around goofy and endearing jokes, sketches, mimicry and games. He also helped to usher in the era of the viral video with segments like "The History of Rap," with Justin Timberlake, starting in 2010; "Slow Jam the News," which President Barack Obama joined him for in 2012; and "The Evolution of Mom Dancing," for which he partnered with Michelle Obama in 2013.

When Fallon replaced O'Brien at Late Night, O'Brien replaced Leno at The Tonight Show — but, following a scheduling dispute, O'Brien vacated that job and Leno returned to it. By 2014, though, Leno was ready to leave once and for all, and Fallon was asked to succeed him and become the sixth permanent host of The Tonight Show, after Steve Allen (1954–57), Jack Paar (1957–62), Carson (1962–92), Leno (1992–2009, 2010–14) and O'Brien (2009–10). He accepted, on the conditions that he could remain in New York, where the program had emanated from until 1972, and that he could retain his Late Night sidekick, Steve Higgins, and house band, The Roots. NBC agreed, spending some $5 million to renovate 30 Rock's Studio 6B — the same one in which Fallon had shot Late Night, and Carson used to host The Tonight Show — into The Tonight Show's new home, which now could seat 240. Retitled The Tonight Show Starring Jimmy Fallon, Fallon's program debuted on Feb. 17, 2014, and was a hit off the bat, thanks largely to its youthful host, a true variety performer who could and would sing and dance and clown around with anyone. Thanks to segments like "Lip Sync Battle" (which soon spawned its own spinoff show), "Thank You Notes" and "Battle of the Instant Songwriters," the show shot to the top of the late-night ratings and became a perennial Emmy nominee for best variety series, landing nominations in the summers of 2014, 2015 and 2016.

Then came the Trump interview, the scathing criticism and the piling on. A month after Trump's visit, the New York Post ran a story suggesting that Fallon's "boozing" had gotten "out of control" and was responsible for several freak injuries that he had suffered in 2015. Then, two months after Trump's visit, Trump beat Hillary Clinton (whose hair Fallon had ruffled on his show the night after Trump stopped by), by winning the presidency, which only further fueled anger towards Fallon. And, ever since Trump assumed office in January 2017, as the entire country has become more politicized, Fallon's show has lost more than one-fifth of its audience and been passed in the ratings by Stephen Colbert's new and more political The Late Show for CBS, while a more politically outspoken Jimmy Kimmel has also propelled ABC's Jimmy Kimmel Live! to major gains in viewers. "The ratings never bothered me," Fallon insists. "I don't really care about the ratings. I never will. That's someone else's job at NBC." Then, a year ago, to add insult to injury, the TV Academy nominated Colbert and Kimmel's programs for best variety series, but not Fallon's.

"It was definitely a down time," Fallon somberly says of the period after Trump's last appearance on his show. "And it's tough for morale. There's 300 people that work here, and so when people are talking that bad about you and ganging up on you, in a really gang-mentality..." Choking up, he continues, "You go, 'Alright, we get it. I heard you. You made me feel bad. So now what? Are you happy? I'm depressed. Do you want to push me more? What do you want me to do? You want me to kill myself? What would make you happy? Get over it.'" Fallon adds, "I'm sorry. I don't want to make anyone angry — I never do and I never will. It's all in the fun of the show. I made a mistake. I'm sorry if I made anyone mad. And, looking back, I would do it differently."

Looking back is not a luxury that Fallon often affords himself — he very rarely grants interviews — because of how busy he is with his wife and two young daughters, and how much time it takes to make quality episodes of TV every weekday. "You have another show tomorrow, so I can't really freak out," Fallon says, and so, he acknowledges, he slaps on a smile even when he's feeling down or sick. To his credit, now, as much as ever, he can be counted on to make funny episodes that lead to widespread conversation and coverage (recent examples include one that he co-hosted with Cardi B on April 9 and another that was essentially taken over by Ariana Grande on May 1), and he still makes time to let loose away from the show (making a May 5 cameo on SNL as Jared Kushner and posting to Instagram a goofy music video that he made with Lin-Manuel Miranda on June 1). But now, maybe more than ever before, Fallon also shows his serious side, both on the show (delivering emotional monologues after the deadly events in Charlottesville, Virginia, on Aug. 14, and the passing of his mom, on Nov. 13) and off it: He sponsored buses to — and he and his family attended — the March for Our Lives in Washington, D.C., on March 24, and he gave the commencement address at Marjory Stoneman Douglas High School's graduation ceremony in Parkland, Florida, on June 3.

Twenty-one months after Trump's visit to The Tonight Show, the fallout from it clearly still weighs on Fallon. But nearly 21 years after the host first came to NBC — "Al Roker's probably the only guy that has more time than me," he cracks — he has no doubts that he pursued the right path in life. "I love what I do," Fallon says. "I'm lucky to work with the people I work with. And I hope I get to do this for as long as people are watching."