Jimmy Fallon’s 10 Most Hilarious Moments of All Time (Warning: You Will Laugh-Cry!)

To celebrate his debut as the newest host of The Tonight Show, take a look back at some of Fallon's best skits.

By Leanne Aguilera Feb 17, 2014 8:00 PMTags
Justin Timberlake, Jimmy Fallon, Saturday Night LiveDana Edelson/NBC

Tonight is your night, Jimmy Fallon!

Now that Jay Leno has officially passed the torch and wished his viewers a heartfelt goodbye in his final Tonight Show broadcast, it's time for a new host to take over. Tonight, Fallon will officially kick off new hosting gig legendary NBC series and to get you ready for all of the comedian's late-night antics, let's take a look back at some of his most hilarious TV moments.

From his 6-year stint on Saturday Night Live to his 969 episodes of Late Night, Fallon has certainly brought us a number of laugh-until-you-cry moments. However, after great difficulty, and hours of YouTube trolling later, we narrowed it down to the top ten. Warning: There's a whole lot of Justin Timberlake ahead... Enjoy!

1. The History of Rap:

Besties Jimmy Fallon and Justin Timberlake never seem to let us down when it comes to their wildly popular "Histories of Rap" videos. From classic like "Push It," "Ice Ice Baby," and "It Takes Two," the dup's musical talents are undeniable, and will bring you a smile in each and every video. Here's the very first one, above. Enjoy!

2. Jimmy's Valentine's Day Songs:

In 1999, Jimmy transformed some of the most popular musical hits into equally catchy Valentine's Day carols on SNL. From Third Eye Blind's "Jumper" to New Radicals, "You Get What You Give," each of these holiday renditions are spot-on and gave  us an early peek into Jimmy's amazing musical skills. 

3. Ew! with Channing Tatum:

Jimmy's Teen-Nick inspired skit has had some pretty hilarious gust stars, (Lindsay Lohan was especially ew-tastic!) but no one else could ever compare to Channing Tatum dressed up as a middle school girl. Bonus hilarity points for when Channing flashed us his best (and most disturbing!) smiles!

4. The Evolution of Mom Dancing:

Of course we had to include this embarrassingly accurate skit of Jimmy and special guest First Lady Michelle Obama, in 2013's Evolution of Mom Dancing. (OK, guys, admit it: Who else has a mom that does the "Just the Hands Part of Single Ladies" move?) Luckily the FLOTUS will be joining Fallon on Thursday, so maybe we could expect a booty-shaking sequel!

5. Celebrity Jeopardy:


In this SNL classic with comedy legend Will Ferrell, Jimmy gives us a spot-on impersonation of Adam Sandler as Ben Stiller giggles his way into a perfect impression of Tom Cruise

6. Slow jamming the News with Barack Obama:

It's one thing to be able to get the President of the United States to guest star on your talk show, it's entirely different (and way more incredible!) when the POTUS slow jams the news with you. The Roots accompanied out soulful duo and helped bring us this unique and surprisingly informative five-minute clip. 

7. Joking Bad:

It's eerie how much Jimmy Fallon resembles Breaking Bad's Bryan Cranston in this spot on parody of the AMC classic. In one of his longest Late Night bits, (Nearly 13-minutes!) Fallon looks to be the top joke dealer in all of late night, and he definitely succeeds. 

8. Dueling Wrappers:

Not surprise here, Jimmy teams up, yet again, with Justin Timberlake in 2013's Christmas episode for another memorable musical moment. In an effort to promote Wrappingville, Jimmy and Justin dressed up in their best paper and transformed some of the most popular songs into Christmas-themed gems. 

9. Egg Roulette:

Jimmy always has the most intense one-on-one battles with his guests, but his ultra-messy Egg Roulette showdown with superstar Tom Cruise is definitely one of the best. Spoiler Alert: Cruise was the first ever Late Night guest to lose so quickly with two raw eggs in a row. The more you know…

10. Debbie Downer's Trip to Disneyworld:

If you don't have tears running down your face right now, then we're pretty sure you're made of stone. We all know that Jimmy Fallon isn't the best at keeping a straight face on live TV, but that's why we love him! You try holding it together while Amy PoehlerLindsay Lohan, and the rest of the table has tears running down their faces because of Rachel Dratch's ridiculously melancholy alter-ego. 

The Tonight Show Starring Jimmy Fallon launches following the Olympics at midnight Feb. 17-20, with the Feb. 21 telecast to air in its regular 11:35 p.m. time slot.

(E! and NBC are both part of the NBCUniversal family.)