Taylor Swift geeking out with Jimmy Fallon is one of the funniest 'Tonight Show' sketches so far

While Fallon is no stranger to donning over-the-top looks, it was Swift’s unexpected transformation that truly stole the spotlight.
PUBLISHED FEB 14, 2025
Jimmy Fallon and Taylor Swift in a still from the latter's talk show. (Cover Image Source: YouTube | The Tonight Show Starring Jimmy Fallon)
Jimmy Fallon and Taylor Swift in a still from the latter's talk show. (Cover Image Source: YouTube | The Tonight Show Starring Jimmy Fallon)

Jimmy Fallon and Taylor Swift have shared a close bond for years. From playful games to jaw-dropping revelations, their on-screen chemistry is rooted in deep admiration for each other. One of their most iconic moments on 'The Tonight Show' was when they did a geeky makeover for an 'Ew' sketch. While Fallon is no stranger to donning over-the-top looks (we all remember him dressing up as a Yeti for Doja Cat), it was Swift’s unexpected transformation that truly stole the spotlight.

Taylor Swift Visits
Taylor Swift visits 'The Tonight Show Starring Jimmy Fallon' at Rockefeller Center on February 17, 2015, in New York City. (Image Source: Getty Images| Photo by Theo Wargo)

For those unversed, 'Ew!' is a recurring sketch by Fallon where he plays Sara, an overly dramatic teenager hosting her own talk show. It mostly features male celebrities as Sara’s BFFs as they gush over their favorite things and complain about their pet peeves. Each sketch also includes an appearance from Sara’s clueless stepdad, dressed in New Balance sneakers and Dockers.



 

As per Today, in August 2014, Swift ditched her popstar image to play Natalie, a nerdy teen with pigtails and braces, while Fallon embraced his over-the-top character, Sara. The appearance had fans in fits of laughter, especially when Natalie sneezed and Sara exclaimed, "Ew! Gross! You are sneezing snot all over the place!"



 

In the segment, Fallon’s Sara tried discussing 'Pretty Little Liars' with Swift’s Natalie, who responded, "My mom hasn’t let me watch television since Miley Cyrus twerked," as per USA Today. Swift as Natalie also shared danced to Selena Gomez’s 'Come and Get It.' This wasn't the only time Fallon and Swift entertained fans with their quirky dance moves.


 
 
 
 
 
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On another occasion, to mark the first anniversary of 'The Tonight Show,' the duo danced on a fake Jumbotron, as per People magazine. The dance routine was part of a sketch called 'NYC Fan Dance Cam,' where they pretended to be caught on camera at a sporting event, dancing wildly and throwing popcorn. 



 

In another appearance on 'The Tonight Show,' in October 2019, Fallon challenged Swift to a fun and lighthearted game of 'Name That Song', as per Entertainment Weekly. 'The Tonight Show' house band The Roots played renditions of popular tracks for the duo to identify. Swift started strong, quickly recognizing classics like Britney Spears' 'Baby One More Time,' TLC's 'No Scrubs,' Nelly's 'Hot in Herre,' and Sixpence None the Richer’s 'Kiss Me,' even recalling that the latter was the first song she ever learned to play on the guitar.



 

The game took a humorous turn when The Roots played Swift's own 2014 smash hit, 'Shake It Off,' and much to her and everyone's surprise, the diva failed to recognize it. Fallon however guessed the song correctly, scoring a point. Embarrassed, Swift jokingly walked off the stage. Fallon and Swift's camaraderie was also evident when the host returned to 'The Tonight Show' following his mother's passing. Swift made a surprise appearance, performing 'New Year’s Day' from her 'Reputation' album. Her lyrics, particularly a line about squeezing a hand three times, a memory Fallon had of his mother, left everyone teary-eyed.

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