Taylor Swift's 5 Best Moments on 'Saturday Night Live'

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Taylor Swift performs on Saturday Night Live on Nov. 7, 2009.

It's been eight years since Taylor Swift last appeared on Saturday Night Live, but certain sketches remain absolutely timeless. Swift was still rocking the long curls and sequined dresses, was filming Valentine's Day -- her acting debut -- and had released Fearless only a year prior. 

In honor of Taylor Swift's upcoming Saturday Night Live performance, which SNL just announced Monday (Oct. 30), Billboard has compiled a list of her five best moments on the show. Watch them all, below. 

"Monologue Song (La La La)" 

In what was probably the earliest moment of self-reference in Swift's career, the singer made fun of her tendency to sing about past boyfriends in a musical monologue. Before mentioning specifics, Swift sang, "I like writing songs about douche bags who cheat on me/ But I'm not gonna say that/ In my monologue/ I like writing their names into songs/ So that they're ashamed to go in public/ But I'm not gonna say that/ In my monologue." Swift mentioned a certain Joe (cough, Jonas, cough) that broke up with her via phone call, before cutting from the music to address Joe and tell him she's doing really well. Swift also brought up the iconic Kanye West beef, which was quite recent at the time, and shouted out her then-boyfriend Taylor Lautner. 

"Teens Raise Awareness About Awful Parent Driving PSA"

Swift donned some heavy metal orthodontic gear and a horrible lisp in this clip to point out parents' horrible driving habits, like lecturing while driving and trying to grab a purse from the backseat while behind the wheel. 


Swift joined Nasim Pedrad and Andy Samberg for this hilarious sketch, where Pedrad is much more interested in hanging out with her bestie, played by Swift, than have a romantic evening alone with her boyfriend. Swift drove the sketch home with a groan-worthy handshake, which the two women chanted along to in unison. 

"Penelope: Wedding"

Swift went head to head with Penelope, one of Kristen Wiig's most noteworthy characters who feels the need to one-up everything no matter what the occasion. Swift's character couldn't help but feel like Penelope was ruining the bride and groom's special day, and stormed off to the bar after offering a killer imitation of Penelope herself. 


Swift spoofed the then-inescapable movie franchise Twilight in this digital short. The singer took on Kristen Stewart's character, falling in love with Phillip Frank, one of Frankenstein's monsters, who replaced vampires.