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.”