Britney Spears’ 20 best songs ranked

Britney Spears sculpted pop music in immeasurable ways. Her perfectly-princess image packaged the Louisana native as the modern era’s answer to Madonna. Given her legacy, what are her best songs?

The indisputable queen of pop, Britney Spears got her start when she was 17 years old, unleashing the quintessential ’90s banger “…Baby One More Time.” It set in motion one of the most impressive and vital pop careers of all time. Her influence is still being felt, particularly with such newcomers as Tate McRae.

Spanning more than two decades, the singer’s career has guided much of what we’ve heard on pop radio in the last 20+ years. From her 1999 debut LP …Baby One More Time to other essentials like 2001’s Britney and In the Zone (2003), Spears moved the needle with not only delicious pop hooks but flashy live performances. She was and is electric onstage; she has that IT factor few others possess.

Spears knew how to deliver those cotton candy choruses with abandon, worming their way into our collective consciences. Here are the star’s Top 20 best songs.

20. “Clumsy”

Guitars rumble right out of the gate. Static pounds from the bass line, leaving Spears to tangle herself in the playful melody. From Glory, the singer has never had so much fun on record.

She’s a veteran artist with nothing else to prove, and it shows. She allows the song it carry itself. Even down to the way she lilts into her head voice is unfussy. It comes so naturally to her, you don’t need much else.

19. “Till the World Ends”

“Sicker than the remix,” this Femme Fatale cut pumps its “ooo”s and “ahhh”s with a high-voltage intensity.

As the world seemingly crumbles down around her, Spears decides dancing will be the best and only way to ring in the apocalypse. “Get me on the floor / DJ what you waiting for?” she asks, the beat sticky and hot. It’s a perfectly rave-worthy banger.

18. “Man on the Moon”

Britney Spears orbits around star-strewn production, twinkling with percussion and other instruments. Spears’ voice is appropriately light and airy, as she spirals through her emotions in her quest for love.

“I can’t compete with the stars in the sky / I am invisible,” she laments. As the song fades, she leaves an imprint on the heart.

17. “Sometimes”

Britney Spears steps out in faith, hoping a relationship will work out. She begs a new beau to move slowly, enough so they both can get their bearings.

“Baby, all I need is time,” she sings. The production glistens, so it seems appropriate then that Spears’ vocals are equally dazzling.

While there’s a rich smoothness to the song, her voice dishes up every single second of emotional currency.

16. “Overprotected”

With her fame growing in intensity in the early 2000s, the then-pop princess attempts to make sense of herself, what’s right, and where she fits into the ever-elusive state of pop music.

As a cherished commodity, Spears had grown used to being examined under a microscope, her every move overanalyzed. This was her statement to the public, a plea to let her live her life on her terms.

15. “Womanizer”

Glittering production takes root, leaving Spears to play around inside a metallic, otherworldly soundscape. “I know what you are,” she coos. Her voice contains a gritty quality, as she sweeps from her lower register into her head voice.

Along the way, she claws her way through the message about empowerment that sets toxic masculinity ablaze. That’s just her way: setting the world on fire.

14. “Don’t Let Me Be the Last to Know”

“I been waiting so long it hurts,” cries Spears. In her most pained vocal performance (and that’s a good thing), the singer reaches into her upper register to squeeze out every ounce of emotion from her chest.

“I need to hear you say you love me all the way!” she pleads. Her relationship resides firmly in the grey area, leaving the singer heartsick and worrisome.

13. “I’m a Slave 4 U”

“Dancing’s what I love,” whispers Spears. “I’m a Slave 4 U” represented an artist sculpting their identity.

While ear candy remained very much in her back pocket, she experimented in a way that demonstrated she had far more to offer than meets the eye.

Even more importantly, she blossomed into a strong and capable woman on the verge of sexual liberation.

12. “Gimme More”

The tabloids wanted more Britney, and she gave it to ’em. With “Gimme More,” her comeback single, Spears owned up to her past, while also acknowledging the media’s role in her downfall.

“It’s Britney, b*tch!” she intros. Despite a troubling performance at the 2007 VMAs, she didn’t let the music suffer. In fact, she hit her stride with Blackout, which remains her catalog-best release. “Gimme More” remains one of many crown jewels in her gilded crown.

11. “Born to Make You Happy”

Spears plucks on the heartstrings with his tattered and torn ballad. Her lyrics drip from an emotional faucet, allowing her to pull in a career-best vocal performance.

“I don’t know how to live without your love,” background vocals echo the forlorn sentiment in a call-and-response structure. From its windswept opening “all my love” whisper to the spine-tingling key change, it’s got all the makings of a classic.

10. “Criminal”

Featuring prominent flute, “Criminal” (from 2011’s Femme Fatale) finds Spears admitting to being in love with a self-described criminal.

“He’s a bad boy with a tainted heart / And even I know this ain’t smart,” she confesses. Her irrational love feeds a part of herself she just can’t deny. It’s a so-bad, it’s so-good sort of love.

9. “Slumber Party”

2016’s Glory was Spears’ return to form. High-fructose doses of pop hooks dressed up with fringe-laced production and some of the singer’s best vocals characterize much of the record.

That’s most evident with “Slumber Party,” a trippy, alluring, and heat-seeking number about intimacy and hooking up. Spears’ voice seduces with its wax-melting quality, as she entices a lover over to her bedsheets. “We use our bodies to make our own videos,” she sings.

8. “Lucky”

Much like “Piece of Me” (also on this list), “Lucky” peeled back the curtain on fame and its toll on its central superstar.

Despite Spears playing narrator and regaling a tale about a girl named Lucky, you can’t help but consider the weight of the lyrics that are ripped from the singer’s own life.

“Lost in an image, in a dream / But there’s no one there to wake her up,” she sings. The price of fame cost her everything (both the character and Spears herself), and that reality lies throbbing at the center of this essential.

7. “…Baby One More Time”

You can’t have a Best Of list without Spears’ monumental debut single. With its music video set in high school, it showcased the problems of adolescence.

As Spears daydreams of the school day being over, she muses on love and wonders if she’s good enough, all set to a giddy backbeat that supercharges the senses.

6. “(You Drive Me) Crazy” (The Stop! Remix)

If you grew up in the ’90s, you know Britney Spears appeared on Sabrina the Teenage Witch alongside Melissa Joan Hart. “(You Drive Me) Crazy” was featured prominently in an episode, courtesy of the Stop! Remix.

In the accompanying video, Hart also made an appearance, making it an official crossover endeavor. It’s guaranteed to get the body groovin’.

5. “I’m Not a Girl, Not Yet a Woman”

As Spears explored grungier music, as she did with “I’m a Slave 4 U,” she kept the cards close to the vest with the sweeping ballad “I’m Not a Girl, Not Yet a Woman” from Britney.

It perfectly captured her transition from childhood to adulthood, especially as someone who grew up in the spotlight. Fame put added pressure on her shoulders, and despite all the flashing lights and extravagant costumes, she was just a person trying to navigate the world underneath the cracking veneer.

4. “Oops!… I Did It Again”

With her second album, Oops!… I Did it Again, Spears demonstrated she was no flash-in-the-pan. She did it again (pun intended) in delivering a body of work that cohesively summed up a particular moment in time.

At the turn of the millennium, songs like the titular cut embodied what made pop music so great. Featuring a slinky melody and sensory-buzzing production, “Oops!… I Did It Again” took listeners across the universe in more ways than one.

3. “Toxic”

Spears exhibited an intoxicating, slithering power with “Toxic.” From In the Zone, this grimy and altogether infectious number planted its flag firmly in our eardrums.

“A guy like you should wear a warning,” she sings, barely above a whisper. Her vocals seduce and entice, luring you into a dangerous dungeon of deliciousness.

2. “Piece of Me”

2007’s Blackout remains Britney Spears’ magnum opus. With its crunchy production and the singer’s filtered, hypnotic voice, “Piece of Me” saw Spears reclaiming the narrative from paparazzi and the tabloids.

“You want a piece of me!” rings the refrain. She wasn’t afraid to call out the media’s portrayal of her life. Coming after the infamous head-shaving incident, “Piece of Me” made quite the statement.

1. “Everytime”

Spears could deliver a wallop of a ballad when she wanted to. With this In the Zone tearjerker, Spears let all her vulnerability and pain pour forth from her soul as though from a fountain.

“Everytime I see you in my dreams, I see your face/ It’s haunting me,” she sings. Haunting strings accentuate Spears’ equally delicate vocal performance. It’s so powerful, a lesser ranking would be unacceptable.