Happy 50th birthday to the man who never fails to bring laughter to our faces, Jimmy Fallon. As the charismatic and beloved host of The Tonight Show, Fallon has not only won over audiences with his infectious energy and goofy charm, but he’s also become a household name synonymous with late-night television hilarity. From his quick wit to his playful sketches with A-list celebrities, Fallon’s ability to connect with viewers has made him a standout figure in the entertainment world.
In honor of this milestone birthday, we’re taking a trip down memory lane to celebrate some of his most iconic talk show moments. Over the years, Fallon has delivered countless laughs through unforgettable sketches, outrageous interviews, and musical parodies that have gone viral. Whether it’s dressing up as fictional characters with Kristen Wiig, lip-sync battling with Emma Stone, or just losing it in uncontrollable laughter with Bradley Cooper, Fallon’s unique comedic style continues to shine and makes him a cherished and irreplaceable host in the world of late-night television.
1. Emma Stone’s Epic Lip Sync Battle With Jimmy Fallon
One of the most viral moments in Tonight Show history is Jimmy Fallon’s lip sync battle with actress Emma Stone. Fallon had previously faced off against stars like Joseph Gordon-Levitt and Stephen Merchant, but it was Stone who stole the show. Her performance of DJ Khaled’s All I Do Is Win had the audience roaring with laughter and cheering her on. Stone’s energy and commitment to the bit, combined with Fallon’s equally enthusiastic performances, made this lip sync battle one of the most-watched segments in the show’s history. The lip sync battles have since become a beloved recurring segment, but Stone’s appearance remains a standout moment that showcased her comedic talents and Fallon’s ability to create viral entertainment.
2. Jimmy Interviews Kristen Wiig as Daenerys Targaryen
One of the most memorable moments on The Tonight Show is when Jimmy Fallon interviews comedian Kristen Wiig, who hilariously portrays Daenerys Targaryen from Game of Thrones. Wiig, known for her quirky and awkward sense of humor, makes no attempt to stay in character or even know anything about the fictional world she’s representing. With poorly fitting costumes and a dragon perched on her shoulder, Wiig stumbles through the interview, inventing nonsensical answers to Fallon’s questions. The entire segment leaves the audience in fits of laughter as the absurdity of the situation grows. Fallon plays along perfectly, reacting to Wiig’s bizarre responses, adding to the chaos. This moment showcases the blend of improvisation and sheer comedy that Fallon and his guests bring to late-night television.
3. Bradley Cooper and Jimmy Fallon’s Uncontrollable Laughter
In one of the most entertaining and unscripted moments on The Tonight Show, Bradley Cooper joined Jimmy Fallon for an interview that quickly went off the rails. Both Cooper and Fallon donned silly visors, which set the tone for a lighthearted and hilarious conversation. However, as they attempted to discuss Cooper’s role in the Broadway play The Elephant Man, neither could keep a straight face. They repeatedly burst into uncontrollable fits of laughter, completely losing track of the interview’s purpose. The natural chemistry between the two, combined with their infectious laughter, made this segment one of the show’s standout moments. Viewers couldn’t help but laugh along as the absurdity of the situation unfolded in real-time.
4. Seth Rogen and Zac Efron in the ‘Ew’ Sketch
Jimmy Fallon’s popular recurring sketch Ew sees him playing the character of a teenage girl named Sara, complete with braces and an over-the-top valley girl accent. In one particularly memorable episode, Fallon is joined by Seth Rogen and Zac Efron, both dressed as equally awkward teenage girls. The sight of Rogen, with his beard and chest hair, in an ill-fitting dress contrasts hilariously with Efron’s surprisingly convincing portrayal of a teenage girl. Their comedic timing, combined with the ridiculousness of the scenario, makes for an unforgettable sketch. Efron’s charm and Rogen’s commitment to the absurdity of his character create a comedy goldmine that perfectly captures the fun and lighthearted spirit of The Tonight Show.
5. Harrison Ford Pierces Jimmy’s Ear on Live TV
Jimmy Fallon has never been one to shy away from an unusual or even risky segment, but one of his most iconic moments came when he invited legendary actor Harrison Ford to pierce his ear live on air. The tension and humor were palpable as Fallon nervously allowed Ford to take a needle and perform the procedure right in front of a live audience. Sweating and shaking, Fallon’s obvious fear made the moment even more hilarious, while Ford, ever the stoic and cool figure, played up the scenario perfectly. Fallon’s commitment to entertainment shines here, proving that no challenge is too big or too painful if it means making his audience laugh. The raw authenticity and comedic timing make this segment unforgettable.
6. The Time Jimmy Fallon Missed His Shot With Nicole Kidman
One of the most cringe-worthy yet hilarious moments on The Tonight Show was when Nicole Kidman revealed that she once had a crush on Jimmy Fallon. During the interview, Kidman recounts a story about visiting Fallon’s apartment years earlier, thinking it was a date, only for Fallon to completely miss the signals. Fallon’s shock and embarrassment upon hearing this in real-time are priceless. His disbelief and regret are evident as he realizes he completely blew his chance with the Academy Award-winning actress. The audience is in hysterics as Fallon awkwardly tries to explain his cluelessness. This segment not only showcases Fallon’s ability to laugh at himself but also highlights the unpredictable nature of live interviews, where anything can happen.
7. Bill Hader and Jimmy Fallon in the Food-Spraying Cop Sketch
When Bill Hader appeared on The Tonight Show, he and Jimmy Fallon recreated a hilarious and gross sketch from their SNL days, where the two play cops who can’t stop spraying food everywhere. Set in a fake ’80s cop drama, the premise of the sketch was simple: Hader and Fallon cram food into their mouths and then proceed to spit it out at each other while delivering their lines. The over-the-top gag of emphasizing the letter P in every word, combined with the sight of food flying everywhere, left the audience in stitches. Fallon’s inability to keep a straight face and Hader’s perfect deadpan delivery made this ridiculous segment one for the history books. It’s a perfect example of Fallon’s willingness to go all-in for a laugh.
8. Jimmy Fallon and Bruce Springsteen Sing ‘Whip My Hair’
Jimmy Fallon is known for his musical sketches, but one of the most iconic was when he and Bruce Springsteen teamed up to perform a hilarious rendition of Willow Smith’s Whip My Hair. Fallon, dressed as Neil Young, performed a folk-rock version of the song, complete with a somber, acoustic arrangement. Midway through the performance, Bruce Springsteen joins him, and together, they create a parody that is both musically impressive and incredibly funny. The contrast between the song’s youthful, energetic lyrics and the slow, melancholic performance is what makes this moment so unforgettable. Fallon’s impressive musical talents and ability to mimic Neil Young, combined with Springsteen’s surprise appearance, had the audience cheering and laughing throughout the entire segment.
9. Will Ferrell and Jimmy Fallon’s Tight Pants Showdown
The Tight Pants sketch is a recurring segment that never fails to get laughs, but one of the funniest iterations featured Will Ferrell. Both Fallon and Ferrell strut onto the stage in ridiculously tight white pants, singing a catchy jingle about how everyone in town loves their tight pants. The absurdity ramps up as Ferrell becomes increasingly aggressive, insisting that he is the only one who can wear tight pants. The escalating tension between the two, combined with their ridiculous outfits and overly enthusiastic singing, creates a comedic dynamic that had audiences laughing from start to finish. Ferrell’s ability to take even the silliest premise and turn it into comedic gold is on full display here, making this one of Fallon’s most beloved sketches.
10. Jimmy Fallon and Justin Timberlake’s History of Rap
Jimmy Fallon and Justin Timberlake’s friendship has resulted in numerous hilarious moments, but their History of Rap segments have become a true fan favorite. Each time the two get together, they perform a medley of classic rap songs, seamlessly transitioning from one hit to the next, all while rapping and dancing with perfect comedic timing. Accompanied by The Roots, these performances are not only funny but also impressive in their musicality. Fallon’s ability to keep up with Timberlake, both musically and comedically, is a testament to their chemistry. The audience’s excitement and the duo’s clear enjoyment of performing together make The History of Rap one of the most iconic recurring bits on The Tonight Show. It’s a segment that showcases Fallon’s versatility as a host and entertainer.
