Jimmy Fallon Picks His Favorite ‘Tonight Show’ Moments With Nicole Kidman, Kevin Hart, Emma Stone and More

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All late-night hosts hope to take their programs to new heights, but “The Tonight Show’s” Jimmy Fallon may not have expected to have to do so on his very first night behind the desk.

As evening approached on the night of February 17, 2014, Fallon found himself hustling up elevators to get to a rooftop at NBC’s 30 Rockefeller Plaza headquarters where U2 was set to perform. Lorne Michaels, the “SNL” executive producer who also has a hand in overseeing “Tonight,” felt the band would look best framed against the dusk, not a dark night sky. So Fallon, having just finished a bit in which celebrities like Robert De Niro and Joan Rivers paid him $100 after betting he wouldn’t get the “Tonight” job, was scrambling to get upstairs before his crew lost the light.

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It wasn’t easy. One of the guests, Stephen Colbert, paid Fallon in pennies, dumping a bucket of the coins all over him. “I got up to the roof just having pennies falling out the back of my shirt, and my underwear and they were in my shoes,” Fallon recalls during a conversation earlier this week, “When I introduced U2, I was out of breath and covered in pennies.”

The host has had little time to get his wind back. Under Fallon’s aegis, “Tonight” has expanded the typical wee-hours format, with guests often asked to take part in sketches, games and jokes, rather than simply plugging a movie or book. Some concepts take weeks, even months, to arrange. Neil Young has appeared alongside a Fallon spoof of himself. Matthew McConaughey once participated in the show’s signature “Tight Pants” segment, in which celebrities dance in constricting white trousers. The actor popped a blister on his hand during the first take, Fallon remembers, leading to a bloody handprint on the seat of the outfit. “It takes the comedy right out,” says Fallon, who notes that a second take — with new white pants — went viral.

The host has been analyzing past sketches and segments for a two-hour special NBC plans to air May 14 to celebrate a decade of his leading “Tonight.” But he already has plans for new things to try. He hasn’t yet taken the program overseas — he says he has considered a stint in Ireland — or had the Pope visit, even thought the “Tonight” team once believed they had a commitment from the Vatican and devised a way to get the religious leader into NBC via underground passageways.

Fallon thinks there will be time. “I still love it. I love to do it,” he says of the hosting gig.

Perhaps Fallon, known for being one of the more garrulous among TV’s late-night coterie, has more to say. Below, he picks some of his favorite segments from the past ten years and offers some behind-the- scenes details about what it took to make them happen.

Near-Date With Nicole Kidman (2015)

What: In a rare, unvarnished moment in late night, the Oscar winner revealed in the middle of a “Tonight” interview that she once visited Fallon at his New York apartment in their younger days to see if she might have romantic chemistry with him. The comedian, who at the time played videogames while serving up brie cheese and saltine crackers, did not impress.

Why: This revelation, says Fallon, was not expected. “I did not know that was going to happen. It was not scripted. It did not go through a pre-interview. It was a legitimate moment, a real awkward moment. I was embarrassed and she was embarrassed.” Kidman has continued to visit the show, says Fallon and he has brought up the anecdote to her husband, Keith Urban.

Kevin Hart’s Wild Ride (2014)

What: The comedian, who does not like roller coasters, accompanies Fallon on a harrowing ride on one of Universal Orlando’s finest.

Why: Fallon, who says he is also no fan of “daredevil-ly” amusement park attractions, convinced Hart to go for a ride on one — and both of their reactions are decidedly honest. Things ramp up when a bug smacks into Fallon’s face in the midst of the chaos. “You actually see a bug explode on my face,” Fallon says. The segment is one of the most viral among “Tonight Show” segments.

President Obama Slow Jams the News (2016)

What: The then-Commander-in-Chief riffs on the headlines, all while backed by a sweaty R&B riff from The Roots.

Why: Setting up this segment took “months of talking” with the White House, says Fallon, who acknowledges that getting the President of the United States to participate in a comedy segment represent “a big swing.” Fallon wanted Obama to say “Ohhhh yeahhh” at the end of the segment and after he requested it, the President said, “Uh, nope.”

“It’s always a abig deal with the White House, and the planning,” Fallon says. In the meantime, he adds, “you hope that nothing is happening in the news that’s sour, so he can do this. When it all works out, we all had a sigh of relief. All the stars aligned.”

“Tonight” Goes to Puerto Rico (2019)

What: Fallon and “Tonight” traveled to San Juan in the aftermath of Hurricane Maria, and ended up shutting down a portion of popular Fortaleza Street to shoot a musical snapshot of the area with Bad Bunny.

Why: The crew had 20 minutes to shoot the segment twice, says Fallon — no small feat with a large entourage that included dancers on stilts, musicians and more. “We had enough time for two takes,” he recalls. “At the end, we had to turn back and do the song again just in case we could do better.”

“Larry Sanders” Tribute (2019)

What: To celebrate five years of Fallon at the “Tonight” helm, the show devised a decidedly non-traditional arc, with a tip of the hat to HBO’s late-night satire “The Larry Sanders Show.” Behind the scenes, Fallon bickered with guests Ben Stiller, Tina Fey and one of the members of Florida Georgia Line tried to get into a sketch against the host’s wishes, Meanwhile, a live audience was on hand for interviews and performances.

Why: “That was really tricky to pull off,” says Fallon. Scripts had to be written for the backstage exchanges, creating fictional storylines that had to be dramatized with a live audience expecting a “real” hour from Fallon. “We really spent a lot of time on that.”

Teenie Weenie Beanie (2023)

What: In a pre-taped segment that seems crafted for new audiences on TikTok. Fallon and guest Paul Rudd wax rhapsodic about tiny ski caps.

Why: Rudd has become “a good friend of the show,” says Fallon, even proving willing in the past to do sketches with the show despite being jet lagged from international travel. For this offbeat bit, “it was just silly little things, but you never know what’s going to pop or go viral,” he says.

Daniel Radcliffe Raps (2014)

What: The actor popular for his portrayal of Harry Potter knocked audiences out with his word-for-word recitation of “Alphabet Aerobics” by Blackalicious.

Why: Fallon and “Tonight” producers regularly ask guests if they have a particular talent they might want to showcase. When Radcliffe volunteered to rap the song, Fallon knew how tricky it would be and told him, “I don’t let anyone fall on my show,” and the fact that “Tonight” is taped in the early evening would work to the actor’s advantage. “He went out and destroyed it.”

Metallica’s Light Touch (2016)

What: Metallica joins Fallon and The Roots to play the hard-rock favorite “Enter Sandman” on classroom instruments.

Why: This one-take performance showed off another side of the headbanging band, says Fallon. “They come off as such a tough band with a tough-guy vibe, and really they are just kind of sweethearts, and really, they just wanted to have fun.” Metallica showed up in T-shirts featuring Fallon or The Roots, whie Fallon and his band wore Metallica garb –all purely by chance.

Emma Stone Lights Up Lip Sync Battle (2014)

What: Stone dazzles the audience with a take on DJ Khaled’s “All I Do Is Win,” complete with a special two-camera shot Fallon says she devised herself. A usable clip of the segment was not immediately available.

Why: Fallon says he gets a kick out of having celebrities surprise the audience with hidden abilities. “It destroyed. It was so loud in the studio. I think that might be one of the loudest reactions that ever happened,” he says.

BTS Meets Fortnite (2018)

What: Fallon asked the BTS crew to emulate movements by characters from Fortnite. They did not disappoint.

Why: The segment helped spark a deeper relationship between the band and the “Tonight Show,” Fallon says. “They always come on our shows and support us,” he notes, recalling a subsequent bit taped at Grand Central Terminal at 2 in the morning that involved music and choreography. “People are nice enough to create these big moments on the show.”

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