Jimmy Fallon First Tonight Show: What Really Happened Behind the Scenes

February 17, 2014. It feels like a lifetime ago, right? NBC was basically banking everything on a guy who used to break character constantly on Saturday Night Live. They moved the whole circus from the sunny palm trees of Burbank back to the gritty, vertical energy of New York City. The stakes were actually sky-high. If Jimmy Fallon crashed, the storied Tonight Show franchise might’ve never recovered from the Conan-Leno-Conan whiplash of the years prior.

But he didn't crash. He giggled, he danced, and he invited about a dozen of the most famous people on the planet to throw cash at him.

The $100 Bet That Changed Everything

You probably remember the visual. Jimmy is sitting at his brand-new, burnished-wood desk in Studio 6B. He looks a little terrified but mostly just happy to be there. He makes a joke about a "buddy" who bet him $100 that he’d never actually host The Tonight Show.

Suddenly, the curtain swings open.

Robert De Niro walks out. No words. He just slams a C-note on the desk and leaves. Then the floodgates opened. It wasn't just a cameo; it was a localized celebrity earthquake. In rapid succession, we saw:

• Tina Fey (obviously)
• Lady Gaga looking regal
• Mike Tyson (because why not?)
• Lindsay Lohan
• Sarah Jessica Parker
• Tracy Morgan
• Mariah Carey (who pulled the money out of her dress, naturally)
• Joan Rivers, marking her first appearance on the show in decades after being banned by Johnny Carson.

The kicker? Stephen Colbert. This was before he took over for Letterman, mind you. He walked out and dumped a literal bucket of pennies—$100 worth—all over Jimmy’s head and desk. "Welcome to 11:30, b*tch!" he shouted. It was messy, loud, and perfect. It signaled that the "cool kids" were officially in charge of the network now.

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Why the Monologue Felt Different

Usually, a late-night host comes out, does five minutes of topical jokes, and gets to the guests. Jimmy didn't do that. Honestly, he spent a good chunk of that first Jimmy Fallon first Tonight Show appearance just introducing himself. He pointed out his parents in the audience. He explained where he was from (Saugerties, NY).

It was a savvy move.

He knew he had to win over the "Middle America" crowd that loved Jay Leno. By being humble and acting like a kid who won a contest, he lowered everyone's guard. He even explained the mechanics of the show. "I’ll come out here, stand on this four-leaf clover, and tell some jokes," he basically said. It was TV for people who might've felt alienated by the snark of the 12:35 a.m. slot.

The Evolution of Hip-Hop Dancing

Then came the first real "Fallon" bit. He and Will Smith—his first official guest—donned denim overalls and performed the "Evolution of Hip-Hop Dancing." They did the Robot. They did the Humpty Dance. When Jimmy tried to twerk, Will Smith walked off in mock disgust.

It was a viral moment before we really used that term for everything. It proved that this wasn't going to be a show of "sit-down" interviews. It was going to be a variety show with a desk in the corner.

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U2 on the Roof of the World

If the studio segments were about being friendly, the musical segment was about being iconic.

NBC didn't just put U2 on a stage. They put them on the "Top of the Rock"—the 70th-floor observation deck of 30 Rockefeller Plaza. As the sun set over the Manhattan skyline, Bono and the boys performed "Invisible." They were backed by the Rutgers University Marching Band.

It was freezing. You could see the breath of the musicians in the air. But the visuals? Incredible. It was a love letter to New York City. Later, they came back downstairs to the studio and did an acoustic version of "Ordinary Love" while sitting on the couch with The Roots.

The Numbers and the Impact

Let’s talk stats for a second, because the industry was obsessed with them at the time.

The premiere pulled in 11.3 million viewers. To give you some context, that was huge. It was the second-biggest audience for the show in five years. Even with the Winter Olympics serving as a massive lead-in, those are numbers that current late-night hosts would probably sell their souls for today.

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People wanted to see if the "kid" could handle the pressure. The critics were generally kind, too. They noted his "unabashed joy" and the fact that he seemed to genuinely care about the legacy of the show, name-dropping past hosts like Steve Allen and Jack Paar.

How to Watch the Premiere Now

If you’re looking to revisit this bit of TV history, you can’t always find the full hour in one place due to music licensing (U2 is expensive, folks). However, you can find the key highlights:

1. YouTube: The official Tonight Show channel has the "Evolution of Hip-Hop Dancing" and the "$100 Bet" segment.
2. Peacock: They occasionally cycle through "Best Of" episodes from the first season.
3. Internet Archive: If you’re a digital sleuth, the full broadcast often pops up here in its original format with the commercials.

What You Should Take Away

The Jimmy Fallon first Tonight Show wasn't just a change of hosts. It was the moment late-night TV stopped trying to be a sophisticated talk club and started trying to be a playground.

If you're a creator or just someone interested in how to make a big entrance, look at how Jimmy handled it:

• Acknowledge the past: He paid respect to Leno and Carson.
• Show your work: He was transparent about his nerves.
• Bring your friends: That celebrity parade was a "flex" that proved he was the new center of the entertainment universe.

It was a masterclass in rebranding a 60-year-old institution for a digital age.

Actionable Insight: If you want to see how much late-night has changed, go watch a clip of Jay Leno’s final monologue and then watch Jimmy’s first five minutes back-to-back. The shift from "jokes for the room" to "bits for the internet" happens right there in that 24-hour gap.