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Miley Cyrus' "50 Ways to Leave Your Lover" Cover Blew the SNL Audience's Mind

When the Grammy-winning "Flowers" singer belted the Paul Simon hit during her wilder pop star era, she gave viewers a lesson in the undeniable power of her vocals. 

By Samantha Vincenty

While she earned her first two Grammy Awards in 2024, Miley Cyrus has enjoyed a successful pop music career for more than 15 years. Since Cyrus first began releasing music in 2007 (under her own name and not her Hannah Montana character's, that is), she's scored twelve top 10 hits on the Billboard Hot 100, released eight hit studio albums, and brought her wealth of industry expertise to The Voice as a Coach in Seasons 11 and 13.

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So for those who may not recall the Miley Cyrus of a decade ago, it might be surprising to learn there was ever a time when some folks had to be schooled in the matter of her vocal talent. But when Cyrus performed a cover of Paul Simon's "50 Ways to Leave Your Lover" at Saturday Night Live's 40th anniversary special back in February 2015, it had been less than two years since the former Disney star had dropped jaws with her all-grown-up BANGERZ album (and a racy MTV VMAs performance). She still was in a creatively-experimental era, in the middle of recording Miley Cyrus and Her Dead Petz. 

RELATED: Miley Cyrus and Her Mom Tish Looked Like Literal Twins at the Grammys

Yet Cyrus set all of the spectacle aside when she sang "50 Ways to Leave Your Lover" on SNL 40. Dressed in a sharp white suit with a Western-style blazer embroidered with red roses—her bamboo earrings the only nod to her aesthetic at the time—Cyrus let her voice take center stage. 

Watch Miley Cyrus sing Paul Simon's "50 Ways to Leave Your Lover" on SNL 40 here.

Miley Cyrus performs on Snl's 40th Anniversary special

Miley Cyrus' Paul Simon cover surprised and delighted viewers

Backed by a band that included former SNL cast member and Fred Armisen, who regularly sits behind the drum kit on Late Night with Seth MeyersCyrus plumbed the depths of her lower register to do Simon's verses justice.

As Dakota Johnson noted during her January 27, 2024 SNL monologue, the SNL 40 studio audience for Cyrus' performance was packed with stars: The photo she shared featured Taylor Swift, George Lucas, Steven Spielberg, Allan Cumming Derek Jeter, 50 Cent, and then-future president Donald Trump, to name just a few, in addition to cast members current and former. 

RELATED: Watch Miley Cyrus and Jimmy Fallon Sing "Jolene" in Disguise in the NYC Subway

After the 2015 broadcast, Cyrus' stage victory made headlines too: "Behind all the drama, the girl can really sing," read a Refinery 29 review. As anyone who watched Cyrus' 2024 Grammy Awards performance of "Flowers" knows, the woman sure can.

Has Miley Cyrus hosted Saturday Night Live?  


Miley Cyrus has hosted SNL three times. She made her hosting debut on March 5, 2011 in Season 36, and returned to pull double duty as Host and musical guest on October 5, 2013, and October 3, 2015. 

She's also been musical guest four times in 2017, 2018 with Mark Ronson, 2020, and most recently in 2021.