Top 20 Funniest Jimmy Fallon Show Moments

During her time as First Lady, Michelle Obama led the “Let’s Move!” campaign encouraging parents and children to stay fit. As part of its promotional run, she danced it out with Jimmy on “Late Night.” The performance takes viewers back, as the pair pays tribute to “mom dances” across previous decades. Getting in full character, Jimmy channels his inner soccer mom while Michelle supports his act. Some old hits like the “Hip Bump” and the “Pulp Fiction” delight the audience. But eventually, it’s clear that Michelle’s got the better moves, and Jimmy has to step aside to let the First Lady own the dance floor. This act was so popular that we got another duet five years later, where Michelle channeled her inner Jimmy Fallon.

We’re yet to see a “Wheel of Impressions” that doesn’t have us laughing in hysterics. This challenge involves singing nursery rhymes. Ariana Grande’s imitations of various artists might just be the best. The songstress inhabits each singer’s mannerisms down to a T. It’s as if we’re really watching Christina Aguilera give it her all…for a round of “Wheels On The Bus.” The wackiness of the challenge’s premise increases the longer it goes. We’ll give Jimmy credit for keeping up with Grande. By the end, we’re treated to a flawless duet between Grande-as-Celine-Dion and Jimmy-as-Sting. Honestly, where’s that Grande-Fallon album we’ve been waiting for all these years?

If you’re from the ‘90s and ‘00s generation, then Matthew McConaughey and Hugh Grant will always be your rom-com leading men. The actors delivered hit after hit in the genre, immortalizing certain words for generations. They finally starred together in “The Gentlemen.” But since they share no scenes together, the pair treated fans to their most iconic lines while on “The Tonight Show.” The twist? They had to utter the other’s quotes. McConaughey, in all his trademark charm and spirit, does the best with Grant’s line from “Love Actually.” However, the funniest moment arrives when the latter delivers McConaughey’s most popular quote with as much mock resentment as he can possibly muster.

When you think of John Travolta, you think of singing, dancing, and a whole lot of style. Jimmy got the best of Travolta all in one, as the performer channels his greatest characters in a “Travolt-Off.” With Jimmy playing along, the two imitate various characters like “Grease”’s Danny Zuko and “Pulp Fiction”’s Vincent Vega. We also get a humorous reprise of Travolta doing Nic Cage doing Travolta in “Face/Off,” and the actor doesn’t miss a step. Travolta and Jimmy then trade insults à la Vinnie Barbarino from “Welcome Back, Kotter” in a deliberately hammy take on the character. Plus, it wouldn’t be Travolta if he didn’t bust out his patented moves, which he and Jimmy use to close out this entertaining segment.

Few people possess as much effortless charisma as Robert Downey Jr. The actor shows his ability to tap into a range of emotions in this amusing skit with Jimmy. The two have a back-and-forth with such random scenarios that the laughs flow in abundance. Starting with annoyingly philosophical attitudes, RDJ and Jimmy shift to wildly contrasting framing devices. From fishing for compliments to staring around smelling bacon, we can’t handle this level of goofiness. The pair’s chemistry works wonders each time, captivating us no matter what emotion they’re portraying. Even the silliest premise can be a hit when you’ve got such talented actors at the helm. Forget “Oppenheimer,” this performance should’ve gotten RDJ his long-overdue Oscar.

Who knew Hogwarts offered rap as an elective? Where else would Daniel Radcliffe have learned to bust a set that would put Death Eaters to shame? A few years after the final “Harry Potter” release, Radcliffe performed an incredible rendition of Blackalicious’ “Alphabet Aerobics.” With Jimmy as his silent hype man, the actor goes through each letter of the alphabet. Radcliffe kicks things up a notch the further he goes, belting out lyrics with magical accuracy as his performance heats up. For “Harry Potter” fans, this segment brings out a side of the actor we didn’t know before. If nothing else, it’s funny to learn that while Radcliffe might be British, his rap voice is American.

Freeman has played too many iconic characters to list, but their common denominator is his voice. His soothing yet commanding voice is familiar, yet Jimmy found a way to put a fresh spin on it. With two balloons at their disposal, Jimmy and Freeman have a conversation in their helium voices. While hearing them vocalize this way is certainly comical, their contrasting attitudes make us laugh. Jimmy is clearly giddy at the prospect of sharing this moment with Freeman, who looks completely done with the former’s antics. Freeman’s deadpan delivery only amuses Jimmy further, who can barely contain himself by the end of the segment. To be fair, neither can we.

As much as we love classic ‘90s sitcoms, many of them have a noticeably cheesy quality. To its credit, “Saved by the Bell” was more self-aware than most shows. This was still evident when the cast reunited for a throwback segment on “The Tonight Show.” It’s as if no time has passed, as the actors embody their roles exactly as they did during “Saved by the Bell”’s run. Jimmy also looks like he’s having the most fun, living out one of his dreams to be part of the cast. Complete with everyone’s catchphrases, trademark behavior, and that solid ‘90s charm, it’s a lovably wacky segment that needs no laugh track to be funny.

Michelle isn’t the only Obama to jam it out with Jimmy. Months before the end of his second term as president, Barack Obama appeared on “The Tonight Show.” Simultaneously a farewell and a humble brag, Jimmy and Obama musicalized the latter’s legacy in office with a valuable supporting performance from the Roots’ Tariq. Jimmy and Obama’s lyrics and delivery mine a lot of humor from the set-up. At the time of this segment’s release, the presidential election was on the horizon, providing some well-timed zingers toward the Republican candidate that got big laughs from the audience. When it comes to bucket list items, Jimmy definitely got to tick one off with this unusual duet.

Fun is guaranteed whenever Kevin Hart visits “The Tonight Show” – mainly because Jimmy finds ways to scare Hart each time. Notoriously averse to anything risky, Hart is forced on a roller coaster ride. It goes just about as expected, with the comedian screaming his way through the entire thing. Not exactly having the heart of a lion himself, Jimmy joins in as well. The latter gets a hilarious surprise when a bug smacks him in the face – not that Hart notices or cares. Just when the comedian thinks it’s all over, Jimmy surprises him with another round, much to Hart’s horror. Speaking of horror, Hart and Jimmy delighted fans with another scare-filled adventure two years later with a trip to the “Blood Manor” haunted house.

Jimmy rose to fame as a member of “SNL,” and made close friends with some pretty famous names along the way, so it’s always a riot when an old cast mate makes an appearance on his show. Things get particularly giggly when the queen of awkward comedy herself, Kristen Wiig, sits down for an interview. A recurring “Tonight Show” bit sees Wiig pose and interview as a famous character – the only problem is she knows nothing about them. Here, Kristen dons hair extensions, royalty-inspired dress, and shoulder-dragon to become “Game of Thrones’” Daenerys Targaryen, hilariously stumbling through questions about Ms. Stormborn. Her answers are way off, but at least they have us on the floor laughing.

If one thing holds true, it’s that Jimmy Fallon is up for ANYTHING if it makes for an entertaining show. In a moment from “Late Night” he’ll surely never forget, Jimmy throws his body on the line, handing Harrison Ford a needle to actually pierce Fallon’s ear on television. The brilliance of the sketch lies in its balance of honesty and showmanship. Fallon is quite clearly legitimately scared, shaking and sweating profusely, while Harrison is as cool as Han Solo, torturing Jimmy and playing up to the crowd. Fallon, ever the entertainer, manages to make a few jokes throughout his surgery… well, between the tears.

Even the biggest Fallon fans will concede that “The Tonight Show” host isn’t exactly the best when it comes to interviewing guests, but even in weakness he can still bring the laughs. In what should have been a pretty standard interview, Jimmy sat down with Bradley Cooper to discuss his role in the Broadway show, “The Elephant Man.” There was no game set up, no performance or sketch, but there was one catch: each wore a football fan visor with silly wigs attached. Despite their best attempts to get serious, neither Cooper nor Fallon could get over the ridiculous gear the other sported, breaking down in giggle-fits throughout the interview.

Can someone tell us why Zac Efron is so attractive even when dressed up as a teen girl? Actually, we’ll get to that in a minute… One of Fallon’s most popular recurring sketches is “Ew!” He’s had stars like Taylor Swift test her acting chops, and while Ariana Grande had a particularly fun appearance, none top Rogen and Efron. As usually, Jimmy is fully committed to his character, Sara, but the hilarity comes from Rogen and Efron. Rogen, stuffed into an ill-fitting dress, sees his chest hair and thick beard proudly on display, while Efron, channeling his “High School Musical” days, fits the role perfectly. Ew?! Well, maybe, but they do take a sidesplitting selfie.

Jimmy is a man of many talents – more than a jack-of-all-trades, he masters them too. Among those talents are a great ear for music, an extensive arsenal of impressions, and a penchant for creativity. In this performance, under a strategic lone spotlight, Jimmy dons hat, wig, and jacket, taking the stage as Neil Young to sing a folk-rock inspired version of Willow Smith’s “Whip My Hair.” Jimmy’s impression is spot-on, the song is impressively orchestrated, and the crowd loves it. Fallon ups the ante when, halfway through the performance, Bruce Springsteen – the Boss himself – joins Jimmy on stage to finish up the song. We only wish they would have whipped their hair!

During a “Tonight Show” interview, Jimmy and Nicole Kidman decide to recount the story of how they first met. As Fallon would soon find out, his version of the story and Kidman’s were quite different. To Jimmy, the story begins innocently with a friend telling him he was bringing Kidman to Jimmy’s apartment, but Nicole quickly asserts that she had a crush on Fallon, and that she actually viewed the meeting as a date. This moment is hilarious because Jimmy clearly had no idea she was interested in him, realizing it right there during the interview. Blushing and laughing, Fallon realized he blew a chance with the beautiful Academy Award winning Aussie.

Like Kristen Wiig, Bill Hader is another friend from Jimmy’s “SNL” days. They must have a close relationship, because there’s no way Fallon could have talked Hader into this outrageous sketch otherwise. The premise is simple: with an ‘80s cop show as the setting, Jimmy and Bill take turns cramming their mouths full of food before spraying each other with the chewed up bits as they come up with every excuse to emphasize the projective letter “P.” Childish? Maybe, but it keeps you laughing from start to finish. Each takes pleasure in preparing final blows, while the other just has to stand there in nervous anticipation. It’s a perfectly presented piece of a playful prop performance.

This recurring sketch may be one of Jimmy’s strangest, but with Will Ferrell in tow, and Jimmy’s commitment at 100%, the “Tight Pants” song and dance gets the laughter rolling. Unbelievably goofy, Ferrell comes out, plastered smile on his face, dressed in ridiculous ‘70s attire, boasting about the tightness and popularity of his white pants. Jimmy joins in on the jingle a few moments later, similarly praising his tight white pants. The duo soon spiral down into a battle of words over whose pants are the tightest and the most talked about, and in classic Will Ferrell fashion, things… get... serious. Ferrell’s deadpan humor is top notch, leaving the audience, but somehow not his pants, in splits.

A large contributor to Fallon’s success as a late night host has been his viral fame; he has a knack for creating content that takes the Internet by storm, and no sketch captures that more than his Lip Sync Battles. While it was special to see Jimmy, Lip Sync Battle executive producer Stephen Merchant, and A-Lister Joseph Gordon-Levitt duke it out in a wild three-way fight, it’s his battle with the wonderful Emma Stone, which has over 75 million views, that dominated the Internet. While we’ve come to expect the best out of Jimmy, it was Emma that killed the game with an all-out rendition of DJ Khaled’s “All I Do Is Win.” Just listen to her go.

Between his tenure on “SNL” and his ongoing run as a late night host, Jimmy’s best-friendship with music superstar Justin Timberlake has served up some amazing skits, but none seem to get a crowd roaring with laughter more than the duo teaching the history of rap. Fallon and Timberlake’s chemistry is uncanny and in sync like, well, NSYNC. The two choreograph each song to roll right into the next, and bust out dance moves to fit the mood. With The Roots playing each hit live in the room, and the Fallon/Timberlake all-star team performing, Jimmy keeps an endless stream of laughs coming whether it’s on “Late Night” or “The Tonight Show.”

Which Jimmy Fallon show moment had you ROFL-ing? Let us know in the comments.