Top 10 Saturday Night Live Breaking Character Moments
#10: “Stefon & Shy”
Top 10 Hilarious Stefon SNL Moments
The brainchild of Bill Hader and John Mulaney, Stefon was introduced in 2008, and quickly grew to become a fan favorite. The world said goodbye to the Weekend Update correspondent – whose knowledge of New York City’s most bizarre hotspots was both hilarious and unparalleled – in 2013. But since then Stefon has still found time to make a guest appearance or two. In 2018, Stefon returned, along with his lawyer Shy – played by Mulaney – and wasted no time getting everyone to crack up – including Hader, and Update hosts Colin Jost and Michael Che. Hader laughs throughout the entire sketch, leading us to believe he was reading the script for the first time. How else do explain it?
#9: “Simon's Dreidel” b/w “Menorah in the Window”
Simon Cowell VERSUS Gordon Ramsay
These two iconic characters have made numerous appearances over the years. Played to perfection by Fred Armisen and Kristen Wiig, Garth and Kat are a song writing team that just can’t seem to find time to rehearse their songs. In fact, to get into character, Wiig and Armisen never rehearsed their performances, something Wiig called “freeing and fun." Perhaps that’s why both actors regularly burst into fits of laughter during sketches, as neither knew what to expect from the other! Watching Wiig try and keep up as Armisen just wings a performance is truly amazing. It’s no wonder they couldn’t keep it together!
#8: “Scared Straight: Underage Drinking with Tracy Morgan”
This sketch from 2009 had no shortage of top-notch comedic talent. Tracy Morgan, Keenan Thompson, Jason Sudeikis, Bill Hader, Andy Samberg, and Bobby Moynihan are all featured; and when that many funny people are in a room together, things are bound to get a little silly. The sketch saw Morgan and Thompson playing convicts attempt to scare a trio of kids who were arrested for underage drinking. The only problem? They keep using the plots of popular movies to describe prison. Thompson and Hader are the worst offenders in this one, but everyone cracks at one point or another. You try making it through without letting a smile creep across your face! ‘Cause this here is real!
#7: “Family Feud Celebrity Edition: NBC vs CBS”
Top 10 Times Phil Dunphy was the Best Character on Modern Family
As long-time friends and collaborators, it isn’t exactly surprising to learn that Justin Timberlake does a mean Jimmy Fallon impression. He got to bust it out during a 2013 appearance on “SNL” during a game of Celebrity Family Feud. And guess who was also playing? Jimmy Fallon. Fallon, whose infamous for his inability to keep it together during sketches, was playing “The Big Bang Theory’s” Jim Parsons. The two celebs went toe-to-toe right off the bat; and immediately had to turn away from the camera to hide their laughter. Later, Timberlake’s impression was so accurate, it caused Fallon to duck behind his podium, struck by a serious case of the giggles. It's classic Fallon…
#6: “Donnie’s Party”
Introduced in 1999, The Boston Teens made regular appearances during the run of Jimmy Fallon and Rachel Dratch. Known for their thick Boston accents and love of the Red Sox – as well as for constantly bickering and making up – the characters regularly caused others to bust a gut. One of the most infamous cases involved Boston boy Ben Affleck, who simply could not contain his laughter while at a party with The Boston Teens. Watching him say “bro” over and over again while struggling to keep it together is priceless. Naturally, Fallon couldn’t keep a straight face either.
#5: “Close Encounter”
It was clear from the first minute of this sketch that host Ryan Gosling was not going to make it through without breaking character. After being abducted by aliens, Kate McKinnon, Cecily Strong and Gosling each recount their experience with the extraterrestrials. However, McKinnon’s version differs wildly from the other two. So much so in fact, that Gosling was basically stifling a laugh for the entire sketch. Strong, Bobby Moynihan and Aidy Bryant all eventually broke; and even McKinnon had to repress a laugh at one point. Later in the episode, Gosling fell victim to a hilarious performance by Aidy Bryant, who’s portrayal of a boundaryless teenager caused him to once again break character.
#4: “Love-ahs in the Hot Tub”
Top 10 Exact Moments We Fell Out of Love with a TV Character
Surprise, surprise, a sketch featuring Will Ferrell and Jimmy Fallon ended in multiple people breaking character. This iconic bit saw Ferrell and Rachel Dratch playing overly-affectionate lovers soaking in a hot tub and trying to play matchmaker to Fallon and host Drew Barrymore. Well, as you can probably glean from Ferrell’s ridiculous costume, it didn’t take long before everybody was on the verge of a full-on meltdown. Tack on the fact that Ferrell later admitted that the goal was to “make Jimmy Fallon laugh,” and you have the recipe for a sketch that’s guaranteed to have multiple broken characters. Need more proof that Ferrell is character-breaking machine? Check out his “Short Shorts for the USA” clip. You’re welcome.
#3: “Happiest Place on Earth?”
Debbie Downer is one of the funniest characters in “SNL's” prestigious repertoire. Brilliantly brought to life Rachel Dratch, DD can instantly transform any situation into a total bummer – for the other characters that is. As far as the audience, cast members and viewers at home are concerned, she’s a riot. One of her most famous appearances occurred at Disney World, where she somehow managed to ruin the “happiest place on earth” with her depressing anecdotes. While Fallon breaks first – shocker – Dratch isn’t far behind. This inevitably caused the whole table to crack up. Horatio Sanz cries and Lindsay Lohan bangs the table in a fit of laughter. All the while Dratch can barely keep it together.
#2: “I Live in A Van Down By the River”
Another Top 10 Breaking Character Moments on Saturday Night Live
Few comedians are as revered as the late, great, Chris Farley. He could make anyone break with his unique brand of physical humor; and often did. While he has a slew of iconic “SNL” characters, you’d be hard pressed to put any of them above Matt Foley, motivational speaker. In the character’s first “Saturday Night Live” appearance, Farley managed to break host Christina Applegate and “SNL” regular David Spade in seconds with his over-the-top performance; which included hoisting Spade into the air and warning the “teens” about ending up like him. He broke everyone else the moment he screamed “I live in a van down by the river!”. It's priceless. Before we unveil our number one pick, here are some honorable mentions: “Cork Soakers” “Barnes and Noble Firing” “Kissing Family: Brecken Brings His Boyfriend Home” “The Californians: Stuart Has Cancer” “Rookie Cop”
#1: “More Cowbell”
Top 20 Breaking Character Moments on Saturday Night Live
Featuring vets like Will Ferrell, Jimmy Fallon, Chris Kattan, Chris Parnell and Horatio Sanz, not to mention the indomitable Christopher Walken, “More Cowbell” is the stuff of sketch comedy legend, and was so the second it began to air. The cast play Blue Oyster Cult, while guest Walken portrays record producer Bruce Dickinson; a man who has a fever for more cowbell. Watching Ferrell gesticulate all over the room in a shirt that’s way, way, way too small, is absolutely side splitting. Walken breaks, Kattan breaks, Sanz breaks, Fallon breaks; even Ferrell breaks! In the pantheon of “SNL’s” worst character breaks, this one takes the cake.
