Jimmy Fallon Talks Ten Years of Tonight, and Why Late Night TV Is Still ‘The Greatest Thing Ever’

When Jimmy Fallon began his run as host of The Tonight Show, his memorable opening bit included an array of stars and celebrities—Robert De Niro, Tina Fey, Mariah Carey, Kim Kardashian, a pre-disgrace Rudy Guiliani, Mike Tyson, Lady Gaga, and more—planting 100 dollar bills on his desk, (Stephen Colbert dumped the whole sum in pennies, saying, “Welcome to 11:30, Bitch”), each allegedly paying off their bets that Jimmy would never be the host of television’s franchise late-night show.

So do they each owe him a thousand now?

As of last month, it’s been ten years since Fallon took over—from Jay Leno—the chair behind the desk at The Tonight Show, bringing it back to its birthplace, New York City. In that decade: a lot of laughs, sketches, impressions, games, music performances, guests. Highs and lows, a pandemic here, a writers’ strike there; millions of views on YouTube and other sites; the usual complement of the thrills and spills and raw eggs of show business splattered on the forehead.

Fallon seems largely unchanged, a guy with an abundance of talent, and an eagerness to tap into all of it, matched by a persona with deep reserves of optimism and bonhomie. In a Zoom call last week, I talked with Jimmy, whom I have known for about two decades, about his Tonight Show tenure so far, and the anniversary special on NBC this May that will mark it.

Along with: the whole world of late-night television as he’s experienced it.

“It’s the greatest thing in the world,” he says, which sounds like vintage, irrepressibly upbeat Fallon; but he means it in terms of respect for what late-night TV manages to accomplish night after night.

“You come in and you find out what’s going on in the news,” Fallon says. “I try to think of a funny topic, or funny angle to it. I’m going to do a song with that person. I’m going to do a sketch with that person. It happens that day. You talk about it at 10 in the morning and at five o’clock you’re doing it. It’s wild. I don’t know how to compare this job to anything else.”

What makes it stand out, Fallon says, is the consistency and the relentlessness of it. “No matter what it is,” Fallon said, “the biggest bit, the most viral thing. Doesn’t matter. We’ve got another show tomorrow.”

The ten-year milestone gave him pause, Fallon says, because, “It’s gone by so fast. It feels like two years, to be honest. We did that? I was in a sketch with Carol Burnett?”

Any anniversary show requires, like vinyl albums of yore, an assemblage of best-of selections. Fallon says, in the process of collecting them, there have been segments he forgot—like taking over Grand Central Station for a BTS performance; or doing a comedy sketch with Bob Dylan.

Bob Dylan? A comedy sketch?

“I was thinking he’d be quiet and wouldn’t talk,” Fallon says. “But he was so charming.”

Bob Dylan, charming?

The bit had to do with Jimmy and Bob watching circus acts (Dylan apparently loves the circus, who knew?) and that was almost enough. They watched a circus act while each having a glass of whiskey. Jimmy then looks away for a moment and Dylan is gone and maybe it was all a fantasy. But the two empty glasses are there.

“Bob did the sketch and it was funny and kind of beautiful,” Fallon says.

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Then there was the night a couple of months ago when Jimmy and Green Day did some busking together (in disguise) in the NYC subway. “That one went really well,” he says. (It was a smash, really, if the enormous throng on the platform was any indication.)

Fallon, of course, was an early adherent of posting videos that went viral on You Tube and other sites. As in “The Evolution of Mom Dancing” with Michelle Obama in 2013 (when Fallon hosted NBC’s Late Night show). That has had about 27 million views.

The viral component is now essential (and existential) to late night, with linear viewing diminished; but reach, across the various byways of the Internet, still impressive. Fallon says he’s always been “into tech” of all kinds, and is aware that “a younger generation has to be reminded about why you would watch these shows.” Meaning his, and those of his fellow network late-night hosts.

But he says conceiving comedy ideas because they might work on on the web is a fool’s errand. “Most of the time if you do that it kind of feels sweaty,” Fallon says. You can’t ask, “Will it be viral?” he said. “It has to be entertaining” just to be used on the television show.

He cites another hit sketch, “Tight Pants,” where he danced—competitively—with Will Ferrell in the mentioned apparel. Originally, Fallon questioned if the idea would work at all. “And now people are going out wearing them as Halloween costumes.” A Tonight Show tight pants sketch with Fallon, Ferrell, and Christina Aguilera has also had 27 million views.

Speaking of Ferrell, Fallon says his one-time cast-mate on “Saturday Night Live” provided a particularly memorable moment of unexpected comedy.

Ferrell was on as a guest, and someone in the audience made a noise like a cat. Ferrell asked if they allowed Bengal Tigers in the audience. That led to Fallon finding the audience member and bringing him on stage, where Ferrell held him on his lap, saying, “Yeah, I brought my tiger to the show.” And when Fallon asked if the tiger could do any tricks, Ferrell said yes, he could talk. The guy happened to be from Germany and the tiger began responding in German.

“It was totally off the rails,” Fallon says.

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Most of these moments will be in the anniversary special, but not likely too many examples of political comedy. Fallon had his moment in the media stocks for mussing Donald Trump’s hair in 2016, but he has long since put that behind him. He now simply acknowledges, “I’m not as political as the other shows.”

Of course in an Election year he expects a steady flow of political jokes, but he says, “I try to hit both sides.” He readily concedes his late-night colleagues will stress political satire much more heavily. “They’re really good at it,” Fallon says. “But that gives me a lane no one else is really in.”

Fallon has a Trump impression, of course, which he can summon at will. (He said he has been refining it after watching the exemplary work of James Austin Johnson on SNL, “the best I’ve ever seen.”) And he recently trotted out his well-crafted Biden (shades, stiff walking gait, lots of “C’mon mans”) in an ersatz video where Biden, lately a Tik Tok adherent, tries out various memes, like Aliyah singing “It Girl,” Cordelia singing “I think I like this little life,” and Queen singing “Bohemian Rhapsody” in a three-sided mirror.

It was funny enough even to amuse Biden, who sent a video response saying, “I’m always happy to be made fun of by America’s most-watched late-night host. But if Colbert wouldn’t do it, you’re fine too, Jimmy.”

Not that there’s any hyper-competitive animosity among late-night hosts, as in the ancient chronicles. Now, as the TV business contracts around them, they seem more like a Band of Brothers, a “happy few,” who might edit the Henry V speech to read: “For he who sheds his audience with me shall be my brother.”

These late-night brothers banded together for a podcast this past summer when the writers and actors were on strike, and no shows were being made. The Strike Force Five podcasts (Fallon, Colbert, Jimmy Kimmel, Seth Meyers, John Oliver) kept the fires burning in the late-night camps.

“I was so happy we did that with the guys,” Fallon says. “We’re friends but we don’t really talk. We talked twice a week” for the podcast.

Now they’re all back to talking to movie stars and celebrities. And those folks need late-night almost as much as the hosts. During the strikes, Fallon argues, “People weren’t allowed to go promote their stuff. Some movies came and went. They didn’t have anyone to talk to about it.”

Or even to bet a hundred bucks that, a decade hence, there will not be a show (or shows) like Fallon’s Tonight Show, where they can dress fancy and pump up their wares.

I sense Jimmy Fallon would still jump to take that bet.

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