You Better Work, Brit: Britney Spears’ 20 Best Singles

Britney Spears Perfume

Coming on the heels of the moderately successful, baffling “Work B**ch,” Britney Spears is firing back on iTunes with her new single “Perfume,” co-written by Sia. Britney’s new disc Britney Jean drops next month, but let’s reflect on an underestimated fact while we process “Perfume”: Britney has a very diverse catalog of singles. Even if I’m skeptical about the reasons her superfans care so much to defend her every move, the “Don’t Let Me Be the Last to Know” balladeer has delivered so many hits, and a lot of those hits are fantastic. Here, we rank the 20 best ones.

(Forgive the fact that “Kill the Lights,” one of my favorites, was never formally released as a single. I’m just trying to be fair here; that’s my prerogatiiiiive.)


20. “Oops!… I Did It Again”

In 2000, only Britney could’ve fronted a music video bold/bizarre enough to include a red-leather (boot-cut) bodysuit and a revisionist ending to Titanic. The song was yet another pounding Max Martin jock jam in the vein of “Baby One More Time,” but it had the gall to predict its own Billboard success with its cheeky, over-punctuated title.


19. “3”


The thing about “3,” Britney’s third Billboard #1, is it wouldn’t work with anyone else at the mic. The squeaky, monotone chorus calls for Britney’s baby coquette patois. It may seem tame compared to the wicked, bass-heavy Blackout material she’d released prior, but “3” makes up for thump with insane catchiness.


18. “Sometimes”

This summertime ballad from Britney’s first album is allegedly one of the singer’s least favorite songs in her catalog, but we’ll have to disagree. Britney’s vocals sound natural, unforced, nostalgic, and sweet, and even if “Sometimes” contains a chorus that sounds like dialogue from The Room (“Sometimes I run. Sometimes I hide. Sometimes I’m scared of you, [Lisa]!”), it’s a TRL-era favorite in the vein of innocent turn-of-the-century jams like Mandy Moore‘s “Candy” and Christina Aguilera‘s “What a Girl Wants.”


17. “Womanizer”

“I got your crazy!” Britney caws in “Womanizer,” sassing the titular lothario. Her first #1 hit since “Baby One More Time” (!), “Womanizer” kicked off the Circus era with playful angst and made you root for Britney’s romantic recovery.


16. “Outrageous”


In the Zone was the last hurrah of “the old Britney,” but she seemed to foreshadow her own tabloid hysteria with this scandalous single.  She literally moans about shopping sprees and her sex drive, and she readily calls the dancefloor a “freakshow.” Might you even call it a… circus, Britney? Hmmm! She’s had this whole thing planned for yeeeeears, y’all.

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