Top 10 Times Jimmy Fallon Broke Character on SNL
#10: “Sandler Family Reunion”
Jimmy Fallon left “Saturday Night Live” in 2004 but over the years has returned numerous times to host or make cameo appearances. This was the case in 2019 when he came back to play Adam Sandler’s grandfather in “Sandler Family Reunion.” The sketch is a funny bit wherein all of Sandler’s family members end up being versions of his past “SNL” and movie characters. For his part, Sandler has a few moments where he breaks, but the biggest happens when Fallon arrives. The instant the two guys turn to look at each other, you can see the huge smiles as they both try to keep it together.
#9: “Family Feud”
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Usually, it’s someone else making Jimmy Fallon crack up during a sketch, but in the case of this one, the person making Jimmy Fallon crack up is, well, Jimmy Fallon. The “Celebrity Family Feud” sketch finds CBS going up against NBC and while Fallon is impersonating Jim Parsons on the CBS team Justin Timberlake is doing his best Jimmy Fallon impression for team NBC. JT does a very funny, exaggerated impression of an awesomely excited-about-everything Fallon and on two occasions it's just too much for the real Fallon to handle. The first time he’s able to turn and look at the big board to hide his laughter. But the second time, the only place he can hide is crouched down behind his podium.
#8: “The Leather Man”
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You know that annoying squeaking sound that leather clothes make when you move in them? Well, imagine a whole sketch based on that premise and you have “The Leather Man.” It’s pretty much a one-joke sketch that works because of how it doesn’t quite work. You see, the leather sounds are produced off-stage and don’t always match in timing with the actor’s movements. The miss-timing almost breaks Fallon, but it isn’t until Horatio Sanz waddles in that Fallon looks like he’s really on the verge of completely cracking up. Which he does after Sanz delivers a line that, based on the look Fallon gives him, might have been improvised on the spot. He also loses it when a rattlesnake bites Horatio on his Sanz.
#7: “Boston Teens: Donnie’s Party”
Rachel Dratch and Jimmy Fallon have appeared as Boston teens Denise and “Sully” in 14 sketched since 1999 and Fallon has managed to get through a number of them without breaking. But not the one from 2000 that featured the teens at a house party hosted by their friend Donnie, played by famous Bostonian, Ben Affleck. Fallon starts to go from almost his first line, but once Affleck goes full Boston “Bro” on him, that’s when both he and Fallon break. This leads to a few more “bro”s than were probably in the original script.
#6: “Gus Chiggins, Old Prospector”
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If this was a list of the times Jimmy Fallon, Darrell Hammond, Seth Meyers, Horatio Sanz, Tracy Morgan, and Chris Kattan all broke character in the same sketch, there might not be many items on it. But the “Old Prospector” sketch would be one of them. In a wonderfully ironic twist that suits this list perfectly, it’s Fallon who gets the character-breaking party started with his first line. And once he breaks, everyone else goes with him. Well, not everyone. We were actually quite impressed with all the extras in the scene who managed to keep it together when the stars around them were breaking up.
#5: “Aquarium Repairmen”
The “Aquarium Repairmen” sketch from 2003 almost didn’t make the list. Not because it isn’t a hysterical time when Jimmy Fallon broke character, because it most definitely is. However, it almost didn’t make the list because Fallon almost made it through the entire sketch without breaking. Fallon and Horatio Sanz play aquarium repairmen who are more interested in making wise-cracks than repairing anything. And for most of the sketch, they make their wise-cracks without cracking up. But just when you think it’s over, there’s an epilogue scene in a physiatrists office and that’s where both Fallon and Sanz lose it completely. They both laugh so hard their fake mustaches come unglued.
#4: “More Cowbell”
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The “More Cowbell” sketch from 2000 is one of the most famous sketches in the show’s history. Rolling Stone magazine ranked it the ninth best “SNL” sketch of all time. And we understand why. This sketch has it all. It has Will Ferrell playing the cowbell, it has Christopher Walken asking for more cowbell, and it has Jimmy Fallon trying, unsuccessfully, not to break. It isn’t all his fault though. According to Fallon, Will Ferrell wore a tighter shirt than he had in rehearsal, which made his gut pop out as he played the cowbell, and “everyone just broke up laughing, and I couldn't stop laughing.”
#3: “Debbie Downer: Disney World”
Debbie Downer was one of the most popular recurring “SNL” characters of the 2000s. And while there were a number of classic “Debbie Downer” sketches, probably the most memorable is that first one from back in 2004. Memorable as much for launching an iconic character as for the laughing fit that took over every actor in the sketch - including Jimmy Fallon of course. There are two key moments that get the giggle train going. The first is the “wah-wah” sound which follows Debbie’s pessimistic comments. As it turns out, the sound surprised the cast, which already had them starting to break. Dratch’s messed up line was the real point of no return though, and by the end of the sketch no one was really holding it together.
#2: “Jeffrey’s”
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The recurring “Jeffrey’s” sketches all feature Jimmy Fallon and whoever is hosting the show that week. Fallon and the host play employees of Jeffrey’s boutique - where the clothes are expensive and the insults are constant. Kind of like Fallon’s laughter throughout. But he isn’t alone. The show’s host, whether it be Sean Hayes, Pierce Brosnan, or Seann William Scott, also break - albeit not as much as Fallon does. The laughter usually really gets going once either Chris Kattan or Horatio Sanz show up. And even if he manages to pull himself together after that, once Will Ferrell rolls in, Fallon is pretty much laughing his way through the rest of the sketch.
#1: “The Love-ahs”
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As we’ve learned, making Jimmy Fallon laugh during a sketch isn’t very hard to do. But when it comes to the “Love-ahs” sketches, that was what they were designed for. As Will Ferrell told Entertainment Weekly, “The basic purpose of every time we did this sketch was to try to make Jimmy Fallon laugh.” And to say it worked, might be an understatement given how much he laughed the first time they did the sketch, when Drew Barrymore joined them in the hot tub. The next appearance featured Winona Ryder in the Jacuzzi with everyone. And while Fallon was able to hold it together longer this time, you can see Ferrell working him and eventually breaking him a couple times.
