Every Britney Spears Song Ranked

A lovey-dovey duet with her sister, Jamie Lynn, from the dark days of the conservatorship. The Spears gals bond over all their happy family memories, clink wine glasses, and sing, “When I’m witchoo, I’m chillin’, I’m chillin’!” Riiiiight. Considering Britney’s testimony about all that went down with her sister and her parents in her long years of captivity, “Chillin’ With U” deserves its own wing in the That Aged Poorly Hall of Fame.

Imagine how bad a Will.I.Am production for Britney called “Big Fat Bass” might be. Now multiply that by 10. You have just imagined “Big Fat Bass.”

Look, Britney wasn’t wrong. Everyone is doing e-mails! But 23 years later, does she get any credit as a prophet? No! “E-Mail My Heart” has been mocked as Britney’s worst song since the day it came out; even songwriter Eric Foster White admits he’s humiliated by it. (When asked if there’s anything he’d change about the song, he replied, “Not write it?”) Fine, go ahead and laugh, but “E-Mail My Heart” sounds impressively undated now, a prescient warning about social media addiction. “All I do is check the screen, to see if you’re OK” — is that so different from how you’re spending today? Admit it, Britney accurately predicted your damn life. So is it actually a good song? I was hoping you wouldn’t ask that. No. Kinda sucks. But still not as bad as “Chillin’ With U.”

If anyone could turn a soda commercial into a great piece of pop trash, it’s our girl. But not this time. Docked a few notches for the title.

Yeah, so K-Fed’s hip-hop career didn’t go far. Who saw that coming? “Crazy” is from his album Playing With Fire, soon after he and Brit immortalized their whirlwind romance in the MTV reality show Chaotic. Yet his rap fame, like their love, was a butterfly too beautiful for this cruel world. He boasts about his “Tupac juice” thug life: “As I march through the valley of the shadow of death/Dark hair on my chest/Wife on my left!” Brit sang the chorus, but even she sounded embarrassed, and this is the woman who sang “E-Mail My Heart.” Federline soon moved on to star in Celebrity Fit Club, alongside Sebastian Bach and Bobby Brown.

Ms. B has the ever-amazing ability to redeem flimsy songwriting with her larger-than-life personality — that’s her superpower. But she can’t rescue “Pretty Girls,” a half-assed attempt to reinvent the “Hollaback Girl” wheel, already a reject from the U.K. girl group Little Mix. Neither Brit nor Iggy seemed to want credit for this flop. (Brit axed it from her next album.) Let’s just say the charms of Iggy seem a bit elusive here.

Remember when Johnny Knoxville went on Jimmy Kimmel Live to present an allegedly deleted Britney scene from Jackass 3D? Where she gets locked in a Port-o-Potty, then launched on a bungee cord, for a sewage cocktail of total disgustingness? Then she punches Knoxville in the nads? Good times. (And totally fake, obviously — Brit was on the show that night to do “Till the World Ends.”) Anyway, “Scream and Shout” sounds how that stunt looked, except she’s locked in a Will.I.Am solo album.

Justin Timberlake shows off his beatbox skills in this song — just a few months before he slimed her in “Cry Me a River.” Sorry, but a Justin-Britney collabo from 2001 is like Germany duetting with France in 1940. 

Britney sounds totally bored, but that just proves our girl has taste. T.I. is in even sorrier shape, boasting, “She love the way I eat her, beat her, beat her/Treat her like an animal, somebody call PETA.”

Britney delivers a tearful apology to her most long-suffering companion: her heart. “Heart, I know I’ve been hard on you,” she sniffles. “I’m sorry for the things I’ve put you through.” Listeners who sit all the way through this ballad might have their own apologies coming.

Not to be confused with “I Will Still Love You.”

Not to be confused with “I’ll Never Stop Loving You.”

Britney was the singer who proved how fiercely expressive a voice could be with digital robo-glitch distortion — she uses AutoTune the way Elvis used the echo chamber, the way Bob Dylan used the harmonica, the way Hendrix used feedback. Some of her most soulful performances come through a haze of synth fuzz. It’s just one of the many ways she changed how pop music sounds. But Will.I.Am can’t even hear it, so he just punches in her vocals syllable by syllable, till it sounds like a “blink twice if you’re in danger” hostage crisis. An atrocity, especially the way he makes her sing the line, “You bring me Zen.”

One of those filler tracks so anonymous that you wonder if Britney’s even heard it. If she missed “Body Ache,” lucky girl. 

Some of us will always adore Brit Brit in her tearjerker-ballad mode — even in her early TRL days, she could transform slush into magic. Some of us even go to bat for “Dear Diary.” (Just keep reading.) But even I have to admit this one is just depressing. A bonus track from Britney, where she tries to teach herself to be all “OK, fine” about all the ways men will let her down and destroy her self-esteem. Yeeesh.

Her dancehall infatuation has taken her on some ups and downs. As you can guess from the title, this is a down-down-down.

Mama B’s ode to her kids is too sweet-hearted to dislike (“I smell your breath, it makes me cry”), but not a track meant for anyone else to hear twice.

The Britney songbook recycles so many similar titles, which might come from her preference for Swedish songwriters who learn English on the job. “When I Found You” is not the same song as “Now That I Found You,” but who’d bother to tell them apart? Probably not even Britney.

A soliloquy where Britney tries to get to know the “Girl in the Mirror” better. She’s crying! She has stories in her eyes! Lullabyes and goodbyes! “Girl in the Mirror” got cut from the U.S. version of Oops! I Did It Again — that’s right, we’re talking about a ballad too sappy for an album with room for “Dear Diary.” Respect! It surfaced on NSync & Britney Spears: Your #1 Requests … And More!, a CD sold exclusively at McDonald’s, which makes all the sense in the world. 

How many times have you sat around the apartment on a stoned Saturday afternoon asking yourself, “What exactly is the most Steely Dan-influenced Britney song?” All the time, right? The answer: “Thinkin’ About You.” So won’t you smile for the camera?

A sincere attempt at capturing the pathos of Madonna’s “Little Star,” though it could have used a few more minutes of effort in the songwriting department.

A reject from her debut, exhumed for the second album. Points deducted for the line “close the doors of doubt.”

In the Zone was such a shocking departure for Britney at the time, going full-tilt into club smut and burning her Mouseketeer bridges. A true visionary, doing true visionary shit. “Shadow” is the only hedged bet on the album — a wretched Matrix ballad the label could take to radio in case her dance experiments failed. But fortunately, her experiments didn’t fail — quite the opposite, as you’ll see way up on this list — so “Shadow” just got left behind by history.

Best moment: the feline “Oooow” that kicks it off.

Britney, awaiting the birth of her first child, prays for insight into “God’s plan.” But truth be told, the Lord would probably rather listen to “Toxic” like the rest of us.

Even though Britney Jean was stronger than people gave it credit for, they sure made her sing a shitload of goopy ballads, which isn’t really her jam.

You know the scene in The Godfather when Marlon Brando weeps over Sonny’s body and says, “Look how they massacred my boy”? Part of being a Britney fan is feeling that way at least once per album. “Trip to Your Heart” on Femme Fatale — why? How did this happen? Who would do such a thing to her? We never wanted this for you, Britney.

If only she covered the INXS song — or even better, “Devil Inside” or “Don’t Change.” Or “Never Tear Us Apart”? “New Sensation”?

A celebrity charity video for “Artists United Against AIDS Worldwide,” produced by Jermaine Dupri and Bono, with a brief Britney cameo. 

“You never know what you got till it’s gone”? Guess this is the closest we’ll get to a Joni/Britni duet.

Another chintzy ballad from the botched second half of Britney Jean. Her “Don’t Cry” doesn’t even compare to Axl Rose’s.

One of the weirdest production disasters in her entire catalog. For the first 90 seconds or so, “Now That I Found You” is a sparse love ballad, with subtle U2-style guitar, not far from what Taylor Swift did on “Tis the Damn Season.” So promising! Then somebody opens the wrong door and it turns into the fugliest goddamn faux-Abba disco-polka jingle you’ve ever heard in your life. Britney deserves a do-over, not to mention an apology from the producers. 

There’s a bloody brilliant sonic flourish in this commitment-issues lament — at the 3:20 point, Britney trills, “I run awaaaaay,” and her voice warps into an eight-second electro-splutter until it trails off into dying sparks. Hats off to production-writing duo Brian Kierulf and Joshua M. Schwartz, the unsung heroes behind so many peak Brit moments.

Britney calling a song “Trouble” is like Springsteen calling a song “Car” or Olivia writing one called “Sad.” Trouble is the oxygen she breathes, and that’s why we love her.

This breakup song perks up at the end, when Britney stages a little phone-chat intervention with herself — it’s like a TRL version of William Butler Yeats’ “A Dialogue of Self and Soul.” “OK, so listen, so then he goes, ‘No matter what I do for you, it never seems to be enough.’ Eeeew! I can’t believe he said that!” But Brit tells herself the hard truth. “One minute everything’s fine, and the next minute, you’re freaking out — it’s like you’re never satisfied!” It segues right into her version of “(I Can’t Get No) Satisfaction.”

She takes a stand against her latest worthless guy, warning him she won’t be crawling back. Nice candle metaphor: “You try to breathe me/But you can’t blow me out.”

Your basic “Oops!… I Did It Again” teen romance.

The cool thing about “Shattered Glass” is how Brit pronounces it “glaaay-yeee-aaas.”

Not to be confused with “Just Like Me.”

Going from “Just Luv Me” to “Just Like Me” on the same album is high concept — a real-time graph of diminished expectations. And Julia Michaels co-wrote them both.

If you wade deep into the soundtrack of Jimmy Neutron: Boy Genius and get past the opening tracks from Aaron Carter and NSync, you will arrive at “Intimidated.” There’s still time to turn back before you reach Aaron’s “A.C.’s Alien Nation.” You’ve been warned.

Cute but cloying, in a way that doesn’t fit the bleary late-night murk of Blackout.

When Brit decides to aim for a Rihanna clone job, she doesn’t go halfway. She’s got some excellent lovergirl patter here, as she says to the trade, “Sweet talk, let’s go, tell me something credible.”

You have to admire Britney’s commitment to making making her reggae cred happen, but this can’t hang with “Soda Pop.”