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.

15. “Hold It Against Me”


Britney unleashed one of her most longing cyber-whines with “Hold It Against Me,” particularly when she bleats, “Because you feel like paradise” and conveys actual angst in that vocoderized haze. But the real reason “HIAM” makes this list is its aggressive, pumping verse with Britney’s flippant voice cruising on the song’s sweet grind.


14. “Overprotected”

“Overprotected” is about one of pop culture’s favorite things: Britney Spears coping with being Britney Spears. Maybe it wasn’t as directly confessional as that other Britney maturity ode (a bildungsroman, really) “I’m Not a Girl, Not Yet a Woman,” but “Overprotected” still grappled with Britney’s Kentwood upbringing and made a functional adulthood seem possible. It’s snappy as hell and one of the most underrated anthem-type dance jams in her catalog. Cheers to sheltered kids trying to deal!


13. “Born to Make You Happy”

It didn’t go anywhere on the Billboard Hot 100, but I’d say — and this is a rough but fair estimate — 100% of Britney’s veteran fans consider this the underrated gem of her early catalog. It’s sweet, effervescent, and energized in that Celine-Dion-“That’s-the-Way-It-Is” way.


12. “Everytime”

Everytime [Single]

When “Everytime” came out, I remember thinking the lyrics and vocals needed a serious rethink, but since ’04, it’s stood the test of time and remained one of Britney’s weirdest, most thoughtful, and arguably sincerest tracks. Cowriter Annet Artani claims the song is a response to ex Justin Timberlake’s “Cry Me A River” (a song whose video featured Timberlake exacting petty revenge on a Britney lookalike), and Britney’s rejoinder isn’t exactly cocky. Her purred admission  of “I guess I need you, baby” could be considered the bleak flipside to “I was born to make you happy.” Bathtub melodrama at its harshest.


11. “Scream & Shout”

I considered not including this song since Britney is merely the featured guest artist, but… come on. Yes, is the overlord of this robotic, Kraftwerk-stiff dancehall blast, but Britney’s mysterious British accent and straightforward instructions make “Scream & Shout” the instant classic I insist it is. Though we’re asked to scream and shout, Britney never lets her spoken-word grit rise above deadpan uber-confidence. She’s the queen, and that means she doesn’t have to be amused.

10. “Circus”

Finally, the banger where Britney pronounces herself a modern-day PT Barnum, then tells she’s willing to be her own insane sideshow. She’s the ringleader, the three-ring superstar, over-caffeinated clown, and ferocious lion tamer in “Circus,” and her brush with the Big Top is enough to make you buy popcorn, sit back with mouth agape, and watch the show.


9. “Gimme More”

In 2008, even your great aunt had to wonder: How would Britney sound after years of traumatizing media attention and inactivity? Turns out the answer is “possessed and processed, but… in a good way.” “It’s Britney, b*tch” is still the chilliest opening of any Britney single, and the squawky, near-belchy chorus of “Gimme More” churns with libido and cynicism. Though the VMA performance may be her most dubious live event, “Gimme More” is still a sonic treat and rightful attention coup.


8. “I Wanna Go”


A line such as “I-I-I wanna go-oh-oh all the way-ay-ay” may look like a jammed Speak ’N Spell, but for Britney, it’s a rock ’n roll motto in the same throbbing vein as “Let’s Spend the Night Together.” You can’t not bop to that bad-ass verse, particularly when she jams, “Lately people got me all tied up / There’s a countdown waiting for me to erupt / Time to blow out.” It’s a fiery, plastic-melting explosion.


7. “…Baby One More Time”

More than 15 years after Britney first appeared on MTV in Catholic schoolgirl regalia, “…Baby One More Time” remains her signature look, song, and moment. Who was this fresh, flirty Mouseketeer? Why is her loneliness killing her? We’re supposed to hit her with what? Britney Jean became a household name the minute she broke out as a solo star, and it’s mainly because this earworm is still menacingly simple (and sinister) pep rally pop.


6. “Till the World Ends”

You’ll remember that I declared “’Till The World Ends” Britney’s best song of the past five years, and that’s because it’s aimed squarely at clubland. Britney knows how to dominate a glowstick-covered floor, and the echo-heavy “Oh, oh, oh, ohhh-oh!” is just gigantic enough for a three-story disco in WeHo. She may be heralding the Armageddon, but we can agree the best way to end the planet is with a thrilling energy overload.


5. “Break the Ice”


The major crime of Britney’s career: “Break the Ice” did not crack the U.S. top 40. Lodged at #43, it didn’t even chart as highly as “Me Against the Music,” which — if you recall — was a battle that Britney and Madonna both soundly lost. The gasping, quick-hitting fervor of “Break the Ice” is one of many highlights on Blackout, and not just because it sounds like the horniest breath mint commercial ever. (Or was that “Breathe on Me” from In the Zone? Tough call there.) It’s a frosty, sugary pick-me-up. Fire.

4. “Stronger”


The clear victor among Britney’s early empowerment tracks, “Stronger” contains the Backstreet-style strut “(You Drive Me) Crazy” (the unofficial #21 on this list), a climactic pseudo-rap, and the proper retraction of the most troubling lyrics on “…Baby One More Time.” “My loneliness ain’t killing me no more!” she announces. And you can tell she’s not lying, because in the video she works the hell out of that empty chair. Fosse cred!
3. “Piece of Me”

Britney earned the VMA for Video of the Year with “Piece of Me,” but it’s the song that really rules — those sardonic, damning lyrics and threatening thump make this the undisputed best thing on Blackout. She’s taking on her haters and critics, and part of her strategy is to annihilate them with a sonic boom of electronics. When she drones the word “paparazzi,” it’s eerier than anything Gaga does on The Fame. I just shivered!


2. “I’m a Slave 4 U”


“…Baby One More Time” is Britney’s most iconic moment, but “I’m a Slave 4 U” was her most important. As the kickoff single from Britney, it proved Britney’s kittenish sexuality had deeper, weirder angles to exploit. With all its Nintendo bleeps and cooed come-ons, you don’t know whether to be grossed out or intrigued, but the song’s insistent throb is too hot and snaky to resist.


1. “Toxic”

Who would ever object to “Toxic” being declared Britney’s best song? Originally offered to Kylie Minogue (as it was co-written by “Can’t Get You Out of My Head” scribe and dancefloor diva Cathy Dennis), “Toxic” is the moment when Britney jumped from “adorable starlet” to “beatification-ready saint.” Those hyper strings! That slurred sexiness! That chirped, one-of-a-kind chorus! It’s the perfect match of song and artist, as “Toxic” combines the playful teasing of Britney’s early tracks and the slithery dancehall commandeering of her later work. And her hottest moment on tape? That closing, slurred pronouncement: “Intoxicate me now / With your lovin’ now/ I think I’m ready now.”