Taylor Swift Once Hilariously Failed to Guess Her Own Song on ‘The Tonight Show With Jimmy Fallon’

The Tonight Show Starring Jimmy Fallon ‘s host Jimmy Fallon has had countless humorous, poignant, embarrassing, and unforgettable moments on his show. When Taylor Swift returned to The Tonight Show to speak with Jimmy Fallon back in 2019, the two played a game called “Name that song.”

The exchange resulted in one of the show’s funniest moments, per The Things ! Fallon outlined the rules before starting to play, saying, “The Roots are gonna start playing a song, one instrument at a time. Taylor and I can buzz in and guess as soon as we know the song. But if you guess wrong, the other person gets a chance to steal.”

“Treacherous, crazy.” the singer commented, joking. Fallon, added as he chuckled, “You can play along at home,” before they got started.

When the game began, The Roots ( The Tonight Show ‘s house band and Grammy-winning hip-hop veterans) began playing the first song Baby One More Time . Fallon lost the first song because he guessed Oops I did it again incorrectly. However, he correctly identified the singer as Britney Spears, and Swift swiftly identified the song, the Spears’ all-time hit, Baby One More Time . “It’s the Max Martin chords!” Swift said, laughing with Fallon.

After Swift won the first round, Fallon predicted Swift would easily defeat him in the game, saying, “I’m so mad! Alright. Ugh. Of course, Taylor’s gonna kill me at this.”

Swift stunned Fallon by immediately remembering some songs and getting ahead of Fallon. When they got to the final song, however, Swift didn’t identify it, which was unexpected given that it was one of her own songs!

“All right, it’s time for the final song,” the host said, joking that “this is worth 10,000 points.” Swift inquired, “Towards what?” Fallon said, “It’s anyone’s game. Whoever wins this, wins the whole game,” getting a lot of laughter from the audience.

Swift listened as The Roots began to perform, but she didn’t seem to recognize the tune they were playing. Fallon bent down over the buzzer, his palm over it, as he listened. As additional instruments joined in, he looked up, as if he recognized the tune, and buzzed in. He guessed correctly, Shake It Off !

The celebrity was nearly stunned at first, breaking out into a smile and beginning to laugh, but she also appeared a bit embarrassed as Fallon danced about the platform, beaming and shouted, “Yeah! Haha! Yeah!”

Looking down, she turned to ironically pretend to walk off the stage. Fallon chuckled as she pointed to her walking, then dashed over to stop her. Fallon caught up to her before she could reach the curtain. “I’m sorry. No, no, no. Come on,” he murmured, still chuckling. “That’s my favorite thing that’s ever happened on the whole show ever!” he said as he reintroduced Swift to the stage.