Jimmy Fallon's 10 Best Tonight Show Moments

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Jimmy Fallon went from being a relatively unknown comedian from Brooklyn, to a cast member on Saturday Night Live from 1998-2004, who later became the host of Late Night with Jimmy Fallon, from 2009-2014. And then last year, he was promoted to an earlier time slot replacing Jay Leno as the host of The Tonight Show. All of this happened in one building, Rockefeller Center in New York City, over the course of 16 years.

The Tonight Show is a talk show where celebrity guests chat about their latest projects or perform their new music. Jimmy Fallon has given the show the comedic facelift it needed after years of Leno and his dry comedy. Not only has the viewership gone up since Fallon took over The Tonight Show, but now you can’t go on Facebook without seeing videos of last night’s show being shared all over your news feed.

His genuine excitement is what makes Fallon so endearing to his fans. He’s relatable because he’s a fan of all his guests, and he’s enthusiastic about having them on the show. He has a lighter, more up-beat personality than his fellow late night talk show hosts, and this shines through in all the games, skits, and musical numbers he performs with his guests.

Johnny Carson hosted The Tonight Show until he was 66, and Leno hosted until he was 63. Fallon is only 40 years old, so we’ll be able to see him goof around with celebrities for a while. Every episode of The Tonight Show has its highlights, but here are 10 of Fallon’s best, and most-viewed on YouTube, moments.

10. Box Of Lies with Jennifer Lawrence

In this hilariously original game, there are nine boxes that neither Fallon nor his guest have seen before. Both the talk show host and his guest pick a box, and open it out of sight of the other person. You tell your opponent what is in your box, and they have to guess whether you are lying or telling the truth. Other stars such as Channing Tatum and Nicole Kidman have played Box Of Lies while on The Tonight Show, but Lawrence and Fallon were a great pair, both being such characters. Lawrence ends up with boxes that include a Rubik’s cube in Jello and an egg roll in a bird’s nest. Fallon gets the win though, after his lie was so ridiculous Lawrence believed him, saying, “If it’s not the truth, you’re a sociopath.”

9. Jimmy Fallon Blew a Chance to Date Nicole Kidman

While on the show, Nicole Kidman admitted to having a crush on Jimmy and that she made their friend bring her over to his apartment so that she could meet him. Unfortunately for Jimmy, he made less than an impression. He offered her cheese and old Chinese food, and put on a video game. She admits to thinking he wasn’t interested because he wore sweatpants and barely spoke to her. They can’t move out of the awkwardness and through embarrassed looks, they talk about how much they love her husband Keith Urban.

8. “Ew!” with Seth Rogen and Zac Efron

When the stars from the comedy Neighbours came by to visit Jimmy, the talk show host brought out his best character. Dressed in a blonde wig and braces, Jimmy plays Sara (with no h because h’s are “ew!”) who invites her friends over to guest star on her basement talk show “Ew!”. This time Allison (Seth Rogen) and Brittany (Zac Efron) come over to take selfies and talk about James Franco. Seeing some of Hollywood’s funniest men in teen clothing and wigs is something that will never get old. Will Ferrell and Will.I.Am have also gotten girly for “Ew!” skits.

7. “Tight Pants” with Jennifer Lopez and Jimmy Fallon

Jimmy, in very tight white pants, a striped turtleneck shirt, and a ridiculous haircut, came out of a gold curtain singing “Everybody’s talking about my tight pants, I got my tight pants, I got my tight pants on.” But when Jennifer Lopez comes on stage also wearing tight pants, they realize there’s no room in their small town for two people with tight pants. With lines like “get lost apple sauce” and “I gotcha hot sriracha,” the two fight over who gets to keep their tight pants popularity. Obviously Jenny from the block comes out on top. Will Ferrell also performed this skit with Fallon in 2012.

6. Bradley Cooper and Jimmy Can’t Stop Laughing

While wearing faux hair sticking out of visors, Jimmy Fallon and Bradley Cooper cannot keep a straight face while talking about Cooper’s play The Elephant Man, a true story about a deformed man. Even after they take off the visors, they can’t stay serious for long enough to actually talk about the play. Fallon falls to the floor while Cooper gets up and walks away.

5. Lip Flip with Tina Fey

With some camera magic, Jimmy’s lips are interposed with his guests’ so that they can pretend to be one another and mock each other. Jennifer Aniston and Billy Crystal have also played the Lip Flip game while on The Tonight Show, but nothing beats Fallon and his old friend Tina Fey. Because of their time on Saturday Night Live and hosting the Weekend Update segment on the show, the pair are comfortable working off of one another on camera. Their mouths too big for each other’s faces, they do accents, beat boxing, and sing a duet of “Endless Love” together.

4. Wheel of Impressions with Kevin Spacey

Hailing from Saturday Night Live fame, it comes as no surprise that Jimmy Fallon has a few good impressions up his sleeve. But when Kevin Spacey came on the show, everyone was blown away by the House of Cards actor, who not only kept up with Fallon but beat the talk show host at his own game. Without any preparation, the wheel of impressions picks a random celebrity and topic. Nothing seemed to throw off these two professionals, who were capable of doing everything from Christopher Walken talking about Trick-Or-Treating to Bill Clinton talking about Ghostbusters with so much ease.

3. Jimmy Fallon went to Bayside High with “Saved By The Bell” Cast

From 1989-1993, Saved By The Bell, a sitcom centered on a group of high school students, was one of the most popular shows on television. Fallon reunites the cast for a skit, where he reminisces about his time spent at Bayside High as a teenager before moving to New York to pursue his dreams and hopefully become a comedian, a talk show host, and date Nicole Kidman. With some clever digs and surprise pregnancies, Zack Morris (Mark-Paul Gosselaar), A.C Slater (Mario Lopez), Jessie Spano (Elizabeth Berkley), Kelly Kapowski (Tiffani Thiessen), and Principal Belding (Dennis Haskins) were all present to make fans’ childhood dreams come true.

2. Lip Sync Battle with Will Ferrell, Kevin Hart, and Jimmy Fallon

Jimmy Fallon has done lip sync battles with many guests, including Emma Stone, Paul Rudd, and John Krasinki. But it was the lip sync battle the night of Superbowl XLIX that stole the show. Drew Barrymore came on to dance with Fallon for a rendition of “I’ve had the time of my life” from the Dirty Dancing soundtrack and Kevin Hart sang John Legend’s “All Of Me” to Will Ferrell passionately. Ferrell performed Beyoncé’s “Drunk In Love” while seductively dancing and “Let It Go” from the Frozen soundtrack and threw glitter that he had hidden in his pocket the whole time.

1. History of Rap with Justin Timberlake

Jimmy Fallon and Justin Timberlake are the best of friends, and that’s apparent when the two of them get together. Not only are they both funny guys, they both have musical talent. Timberlake, being a nine-time Grammy Award winning artist, and Fallon, who has harmonized with Billy Joel, filled in for Bono when he had to cancel his appearance on The Tonight Show, and sang on stage with Neil Young. What’s surprising is that Fallon and Timberlake are huge rap fans. The two of them have gotten together five times to perform a “History of Rap”, medleys of popular rap songs throughout the years.