Home Music Music Lists

Every Britney Spears Song Ranked

The world keeps counting her out, and Britney keeps coming back stronger than ever. So let’s celebrate one of the most influential artists of the last 25 years by counting down every song she’s ever done — from world-changing hits to under-appreciated classics to “E-Mail My Heart.”

Toni Anne Barson/WireImage; Dave Hogan/Getty Images; Alberto E. Rodriguez/Getty Images

All hail the pop queen: It’s Britney, bitch. The legend. The innovator. The one and only Mrs. Oh My God That Britney’s Shameless. The woman who’s built up one of the all-time great pop songbooks, even as the world keeps trying to dismiss her as a fluke. It’s crazy how we’re nearly 25 years into the Britney Era, yet people still underrate her artistic impact, because they fixate on her image or her fashion. But of all the gifts Britney Spears has given this planet, it’s her music that comes first.

So let’s celebrate that music. And let’s break it down: all 170 Britney songs, counted from the bottom to the top. The hits. The obscurities. The flops. The deep cuts, B-sides, bonus tracks, covers, duets, loosies, soda commercials. Her club classics. Her radio jams. Her buried treasures. “E-Mail My Heart.” All of it. 

As Rolling Stone’s resident Britney expert since the TRL days, I’ve been writing raves about her brilliant music since “…Baby One More Time” was her only song. I got used to people telling me how wrong I was to praise her records to the skies — hell, Britney was one of those people. (How she laughed at me when I told her “Satisfaction” should be a single! Well, you called that one right, B.)

But she’s one of the most influential, innovative pop savants ever, with a massive impact on how music sounds now. It’s been a long-running kick to see her keep evolving, from MTV teen princess to Vegas diva to avant-disco pioneer. No matter how many times she gets written off as a joke, she always surges back, stronger than yesterday.

These days, people love to argue about Britney — her scandals, her controversies, her brave fight for independence. Yet it’s still so taboo to give her credit for her actual music, because people want to pretend she’s some kind of innocent bystander on her own hits. Sorry, but that’s just not credible, given the freakishly consistent sicker-than-the-remix excellence of her artistry. She’s always made the fizziest, splashiest, bestest pop tunes of the moment. I get why you might have issues with calling it “brilliance,” but I do not happen to share those issues — she’s on her own Mount Olympus of brilliance, and always has been. She deserves to be celebrated as one of history’s boldest pop visionaries, not just a case study in celebrity.

The songs on this list aren’t ranked by commercial success, just the level of Britney splendor. Every fan would compile a different list — that’s the beauty of it. You’re guaranteed to disagree, especially when you get to “Dear Diary.” Some of these songs are classics; some are total disasters; one is “E-Mail My Heart.” But let’s face it — they’re never boring. Britney does not do boring.

We’ve seen so many pretenders to her throne come and go. We’ll see more of them. People keep waiting for Britney to be over. They can keep waiting. When people stop claiming Britney’s over, I guess that’ll mean she’s finally over. But they won’t. And she won’t be. So thank you for these songs, Britney Spears. And gimme more.

From Rolling Stone US

Play video

Kevin Winter/Getty Images

68

‘Perfect Lover’ (2007)

Keri Hilson summed up Blackout aptly in The Fader: “We were given the specific direction that she did not want the music to mimic her personal life. So we figured, OK, so let’s create a fantasy world that she would be happy in.” That’s exactly what happens on “Perfect Lover.” Britney inhabits an artificial world all her own, falling in love with a beat that satisfies her more than any flesh-and-blood lover can.

Play video

Peter Kramer/AP

67

‘Out From Under’ (2008)

A poignant guitar ballad about a woman trapped in a suffocating relationship who finally escapes — a story Britney has lived on so many levels. Musically and lyrically, “Out From Under” feels like a prequel to “Passenger” a few years later.

Play video

Kevin Kane/WireImage

66

‘Like a Virgin/Hollywood,’ Madonna feat. Christina Aguilera, Britney Spears, and Missy Elliott (2003)

The 2003 MTV Video Music Awards began with a bang: Britney dressed up in Madonna’s vintage white-lace bridal gown, emerging from a giant wedding cake to sing “Like a Virgin” onstage at Radio City Music Hall. Then Britney shares a forbidden kiss with Madonna herself. It segues into “Hollywood,” with Christina Aguilera and Missy Elliott. (I was a writer on the show, so we all snuck down to see these rehearsals — which meant an entire afternoon of Madonna and Britney making out.) Madonna put the MTV VMA performance on her Remixed & Revisited album.

Play video

John Shearer/WireImage

65

‘Seal It With a Kiss’ (2011)

Britney sets up a secret rendezvous — in public, these two pretend to be just friends, but it’s different “in the shadows where it’s hot.” There’s pathos in the way she keeps sighing “I want you like that.”

Play video

Thomas Kienzle/AP

64

‘Quicksand’ (2008)

Back in 2008, right in the final minutes before Stefani Germanotta blew up into the Mother of all Monsters, she wrote this bad-romance piano ballad for Britney. You can still hear Lady Gaga’s vocals in the background. “Britney is a nice girl,” Gaga said at the time. “I used to scream for her in Times Square, and now I work for her. When I was 13, she was the most provocative performer of my time!” (You have to admit, that’s shade worthy of a Bette Davis movie.)

Play video

Leonid Naidiouk/AP

63

‘Up N’ Down’ (2011)

“I got all tricked out and came out to this thing/Looking so fire hot, a 20 out of 10” — love it when Freakney is feeling herself. “Up ’N’ Down” goes hard in her predator mode — “the beat just dropped and the room got sexy” — as she prowls the club, pouncing on the lap of her new conquest. Max Martin and Shellback help her go for vintage technotronic kicks. A flawless Femme Fatale banger that didn’t fit on the original album but defines it anyway.

Play video

Kevin Winter/AMA/Getty Images

62

‘And Then We Kiss’ (Junkie XL Remix, 2005)

An unusual item in her songbook: “And Then We Kiss,” as remixed by Junkie XL, the kind of smoothed-out, sophisto Europop she’d never much fancied before. It would made a clever left-field pick for the closing credits of a movie romance with a bittersweet ending.

Play video

Youtube

61

‘Slumber Party,’ feat. Tinashe (2016)

Her steamy sleepover with Tinashe has a warm, woozy vibe that evokes Janet Jackson’s The Velvet Rope. If “Slumber Party” had been the leadoff single from Glory instead of “Make Me…,” that album might be remembered very differently now.

Play video

Michael Loccisano/FilmMagic

60

‘Mannequin’ (2008)

The scariest of “Mannequin” songs — B flosses on the catwalk, but behind the glitz, she can feel herself turning into a life-size plastic doll. “I’m frozen, I’m posing” — what an image for the celebrity damage she was going through at the time. What can it mean that the title role in Mannequin was played by Kim Cattrall, who breaks Brit’s heart so rudely in Crossroads? 

Play video

Matt Sayles/AP

59

‘Rock Me In’ (2008)

An underrated New Wave nugget from the Circus sessions, with jagged rhythm-guitar blurts from Greg Kurstin and Nicole Morier. If “Rock Me In” had come from some unknown band with studded belts, leather bracelets, and emo fringes, it could have brought down the house at the When We Were Young Festival.

Play video

Chris Carlson/AP

58

‘Early Mornin’’ (2003)

Finally, a song where we get to hear Britney yawn. “All right, I was out a little late last night,” she explains. “Got a little messy.” “Early Mornin’” is a superbly sultry R&B jam from In the Zone: She walks us through a night in her life, shaking her ass from club to club to hotel and back to club. She gets home by dawn, passes out on the couch, wakes up to do it all over again.

Play video

Tony Avelar/AP

57

‘Selfish’ (2011)

Let’s face it, Femme Fatale should have been a double album. Any other star in the biz could have built a career on “Selfish,” but for Britney, it’s just another amazing unknown bonus track. She flexes some of her favorite vocal poses in the mirror, to a Stargate synth-disco boom. She also tries some playful topping (“Sit down, shut up, who’s the boss now?/I’m about to show you now that I’m a girl and you’re a boy”), with fantasies quoting OutKast, Joni Mitchell, and James Brown. 

Play video

Michael Caulfield/WireImage

56

‘Chaotic’ (2005)

From her MTV reality show with ex-husband K-Fed — Chaotic, they called it, wonder why. Give Brit credit for capturing the sound of a dizzy romance spinning out of control. “Do you like the way I rock it? Boy, I think it’s so chaotic!” That’s fair warning.

Play video

Jeff Kravitz/BBMA2016/FilmMagic

55

‘Man on the Moon’ (2016)

“Man in the Moon” is another one of her Bowie space trips — she’s so great at these that she should just do an all-out sci-fi Britney Stardust album. She pines over a Major Tom astro-boy who’s stolen her heart and then left the planet (“Send my message into outer space/Wonder if it’s gonna float your way”) and sobs, “Houston, I know there’s a problem!” The melody comes from Leonard Cohen’s “Hallelujah,” which makes zero sense, but that just makes it more strangely touching.

Play video

Youtube

54

‘I Love Rock ‘N’ Roll’ (2001)

Her cover versions are such a crucial part of her game, and this Joan Jett cosplay is a prime example. It’s an iconic scene in Crossroads: Britney enters a karaoke contest at a sleazy New Orleans dive, so she and her BFFs can get their car fixed on their road trip. Britney wins the cash prize by belting “I Love Rock & Roll” in a “Freedom” crop top, because America. Bonus: The karaoke host is played by old-school hip-hop legend Kool Moe Dee. Brit explained she did “I Love Rock & Roll” because “I love Pat Benatar!” (Close enough, right?) “It’s like she’s a rock & roll chick and she’s just having a good time, and it’s a very empowering song.” Twenty years later, Brit still doesn’t give a damn about her bad reputation.

Play video

Youtube

53

‘Born to Make You Happy’ (1999)

A 16-year-old weeping “I don’t know how to live without your love”? If that isn’t authentic teen-girl melodrama, what is? Best moment in the video: Britney and her guy slip off to the bedroom for a sensual pillow fight. Obviously, she wins.

Play video

Gabe Palacio/Getty Images

52

‘(I Got That) Boom Boom,’ feat. Ying Yang Twins (2001)

A milestone of cowgirl crunk, with Atlanta hip-hop duo the Ying Yang Twins and a banjo groove. Like our yeehaw queen says, “This is for all the Southern boys out there!”

Play video

Chris Polk/FilmMagic

51

‘Brave New Girl’ (2003)

“There’s a brave new girl, and she’s coming out tonight” is such a quintessential Brit hook. She perfected the concept of shy girls copping a badass attitude and forcing themselves out onto the floor. “Brave New Girl” is serious Madonna worship — it rips both “Material Girl” and “Ray of Light”? — that could have made a perfect theme song for a high-school sitcom on the WB. Bonus points for the title, quoting Shakespeare’s The Tempest in the scene where island-girl Miranda sees other humans for the first time, the Britney-est moment in all the Bard’s work. (But we could go on all day about the countless Shakespeare-Spears connections.)

Play video

Dave Hogan/BCU18/Getty Images

50

‘Mood Ring (By Demand) — Pride Remix’ (2020)

“There’s only one bitch. The real one. Britney.” Well then. The DJ Mustard-produced “Mood Ring” was originally a bonus track on the Japanese deluxe edition of Glory. But in 2020, with the Free Britney movement on the rise, online fans led a #JusticeForGlory campaign to get her 2016 album charting again. Brit dropped “Mood Ring (By Demand)” as a thank-you to the faithful in late May — then watched it top the U.S. iTunes sales chart, just in time for Pride. The song’s rebirth seemed to symbolize hers. 

Play video

Youtube

49

‘My Prerogative’ (2004)

Britney raises a Cheeto martini to the Eighties hit from Bobby Brown, the Teddy Riley collab that helped invent New Jack Swing. But Britney really sinks her fangs into the chorus — “Everybody talking all this stuff about me/Why don’t they just let me live?” She sings “My Prerogative” like it’s her life story, which it is.

Play video

Kevin Winter/Getty Images

48

‘Do You Wanna Come Over?'(2016)

A Britflix-and-chill booty call, cooing over a frisky acoustic-guitar loop. “Do You Wanna Come Over?” makes a late-night “u up?” text sound like a political statement, as she boldly declares, over and over, “Nobody should be alone if they don’t have to be!” Who could argue with that? As Britney told Matt Lauer in her classic 2006 Dateline interview, “I think everybody should be pro-love, you know?”

Play video

Frank Micelotta/Getty Images

47

‘Don’t Hang Up’ (2003)

An overlooked gem from In The Zone, an airy synth-disco focused on her breathy ardor. Don’t worry, B — if he hangs up, you can always e-mail his heart. She wrote it with one of her fave songwriting duos, Brian Kierulf and Joshua M. Schwarz, who penned TRL-era classics like Aaron Carter’s “Aaron’s Party (Come Get It),” Nick Carter’s “Girls in the USA (Featuring Mr. Vegas),” and Willa Ford’s “I Wanna Be Bad.”

Play video

Bernd Weissbrod/picture-alliance/dpa/AP

46

‘Rock Boy’ (2008)

One of everyone’s favorite Britneys: the leather-chick headbanger who sounds like she spent the Eighties prowling the Sunset Strip metal clubs with a switchblade in one hand and a spare can of Aqua Net in the other. “Rock Boy” is where she turns into MotNey Crue, snarling “Meet me in your dressing room” like she knows she’s the real star of the show.

Play video

Rob Verhorst/Redferns/Getty Images

45

‘Showdown’ (2003)

“I don’t really wanna be a tease/Would you undo my zipper please?” Britney, always there to cut to the chase. “Showdown” is one of the first of her many killer collabs with Bloodshy and Avant, with Britney whispering her salacious come-ons.

Play video

James Devaney/WireImage

44

‘Over to You Now’ (2005)

A summit of electro-pop legends: Robyn and Imogen Heap pitch in to write a Britney disco banger. And even by her standards, it’s a filthy one. In “Over to You Now,” Brit invites her lover to go somewhere secret, somewhere new. “Do you like this? This place that I’m bringing you to? Because I do!” My, oh, my — wherever could this location be? “This special place, it’s in the basement,” she explains. “It’s kinda hard to find the entrance/You need some juice.” In case you’re not getting it, she keeps moaning, “Oh, my God!” Happy travels, you two.

Play video

Michelangelo Di Battista/Sony/RCA/Getty Images

43

‘Passenger’ (2013)

The most shameless “Halo” rip ever — but there’s no sin in that, since every artist should rip “Halo” at least once. Britney hits the road with her lover at the wheel, finally trusting somebody enough to be a passenger. (“My hands in the air while you’re driving/This is living!”) Katy Perry, Sia, and the rest of the writing team came up with a seriously touching lyric, too. Britney earned her halo — I just wish “Passenger” came out in time for the Crossroads soundtrack.

Play video

Youtube

42

‘Don’t Let Me Be the Last to Know’ (2000)

Britney tries to get a little emotion out of her boyfriend (hmmm — anyone we know?), but like the dude in an Olivia Rodrigo song, he’s not the compliment type. Herb Ritts directed the steamy beach video, in the mode of his classic clips for Chris Isaak’s “Wicked Game” and Madonna’s “Cherish,” with Britney wearing an impractical macrame bikini. “Don’t Let Me Be the Last To Know” was written by Mutt Lange and Shania Twain; as Shania-Britney moments go, it’s up there with the great Crossroads scene where Britney sings “Man! I Feel Like a Woman!” 

Play video

Tony Avelar/AP

41

‘Telephone (Demo)’ (2010)

Her demo of the Lady Gaga classic, before the songwriter turned it into her own hit. The bare-bones “Telephone” demo leaked in 2010; Rodney Jerkins strips it down to the sound of a plucked harp and a jaded party girl strung out on AutoTune paranoia. The song will always belong to Gaga and Bey, but the intensity of this demo is pure Britney.

Play video

Dorothea Mueller/Keystone/AP

40

‘Touch of My Hand’ (2003)

It makes sense that one of her most openhearted love songs is a tribute to, well, the touch of her hand. She makes her solo date night so romantic, murmuring, “I can draw the blinds and teach myself to fly.” Britney has always called it one of her most personal songs, and one of her favorites. “I really love the vibe of ‘Touch of My Hand,’ ” she said. “I love the subject that, you know, I’m touching on because no one’s really talked about some of those things in a lot of songs written lately because people are scared to go there and to express themselves in that way. And, you know, I think it’s an empowering thing for girls.” 

Play video

Max Morse/Getty Images

39

‘Don’t Keep Me Waiting’ (2011)

Our girl is so underrated as a rock & roll queen, with air-guitar anthems like this one. “Don’t Keep Me Waiting” is Britney in “listens to the Strokes once” mode, a Darkchild-produced bonus from Femme Fatale, stuck on Meet Me in the Bathroom-era NYC garage punk. She slides from a Karen O squeal to one of her funniest fake English accents. If you’re matching Britney’s songs with her fragrances, this one is definitely Rocker Femme Fantasy, which combines top notes of blackberry, coconut, and whipped cream for a scent that is feminine, fresh, and light. 

Play video

Youtube

38

‘Break the Ice’ (2007)

“My heart’s beating like an 808,” she pants — as if they’ve invented an 808 that can keep up with her. “Break the Ice” sums up the Blackout vibe: the red-eyed club-goggles electro-wooosh frazzle of a Saturday night that’s dragged on till Tuesday. 

Play video

Youtube

37

‘Do Somethin’’ (2004)

Brit-Brit was on such a relentless creative roll at this point that people were worn out with the way she kept jumping from one great hit to another. “Do Somethin’” was her way of daring the world to keep up with her, as she jeers that it’s time to get your back off the wall and rise to the challenges of the Britney lifestyle. Excellent question: “What you gonna do when the crowd goes ayoooo?” 

Play video

Youtube

36

‘Hold It Against Me’ (2011)

The first taste of Femme Fatale turned out to be a totally accurate teaser of a ridiculously great album. “Hold It Against Me” is her hyper-aggressive electro lechery, with a weird breakdown in the middle where she moans, blows kisses, and snaps her gum. The lyrics are in Austin Powers-Benny Hill territory: “If I said I want your body now/Would you hold it against me?”

Play video

Youtube

35

‘Radar’ (2007)

For legal reasons, “Radar” was featured on both Blackout and Circus, but with a song like this, expertly devised by Bloodshy and Avant, and the Clutch, nobody would complain if she slapped it on all her albums. She recorded her vocals the day after she filed for divorce, which might explain the extra heat she puts into ready-to-mingle sentiments like “Confidence is a must/Cockiness is a plus/Edginess is a rush.”

Play video

Youtube

34

‘From the Bottom of My Broken Heart’ (1999)

Could we just take a moment to honor this video? Grunge Britney, with her fuzzy bucket hat, oversize cardigan, and denim bell-bottoms. Sitting pensively in her tree swing, beads and braids in her hair. Purple eye-shadow. Packing up her suitcase to hop on the bus and leave her small-town home, because that’s what you do when your heart is broken. Some fans do not feel this song or this video. You just can’t reason with these people. 

Play video

Youtube

33

‘Circus’ (2008)

“There’s two types of people in the world/The ones that entertain and the ones that observe.” Guess which kind Britney is? “Circus” is her defiant statement about living her life in the public eye, explaining, “I’m a ‘put on a show’ kind of girl.” “Circus” twists the invasion-of-privacy realities of celebrity life: Any time Britney walks into a room, she turns it into a spectacle where she’s the ringmaster, cracking the whip and turning the rest of us into her extras.  

Play video

Kevin Mazur/WireImage

32

‘Get Naked (I Got a Plan)’ (2007)

One reason Blackout came out so great: Everybody involved assumed it was a commercial bomb, so they could beta test any crazy idea, figuring there was no risk because nobody would ever hear it. “We were able to create without any distractions, or anyone giving us any real direction,” producer Danja said. “We were free.” You can hear that in “Get Naked (I Got a Plan)” — there’s no real song, just an electro-sludge loop and a brilliant title, yet that’s all they needed for five minutes of divine funk madness.

Play video

Youtube

31

‘I’m Not a Girl, Not Yet a Woman’ (2001)

From the cinematic masterpiece that is Crossroads. Britney writes this song as a poem in her diary, while on her road trip to reunite her birth mother, played by Kim Cattrall. (Which means her parents were Dan Aykroyd circa The Blues Brothers and Kim Cattrall circa Porky’s? Makes you think.) She sings “I’m Not a Girl” at the end, and we all realize things have got way learned. For some insane reason, the Oscar for Best Actress went to Nicole Kidman for playing Virginia Woolf, but Woolf herself would have been the first to say Britney earned it.

Play video

Youtube

30

‘Me Against the Music,’ feat. Madonna (2003)

Two goddesses. One cage. Yet both emerge victorious. Madonna and Britney go face to face on the dance floor, like Obi-Wan matching lightsabers with Darth Vader. They call this a “friendly competition,” but Brit’s a lifelong Madonna fan, so no way is she falling for that shit — she knows that with Ms. Ciccone, there’s no such thing as friendly competition. “Me Against the Music” brings out the beast in both of them. Every time Madonna coos, “Hey Britney!,” an angel gets her wings.

Play video

Youtube

29

‘(You Drive Me) Crazy’ (1999)

If you were a fan of the Backstreet Boys’ “Larger Than Life,” you probably also loved Brit’s “(You Drive Me) Crazy,” since they have the exact same backing track. Max Martin, have you no shame? “Crazy” became the summer-’99 theme for the Melissa Joan Hart/Adrian Grenier rom-com, with Britney playing a waitress in the MTV video. Melissa and Britney also bonded on a very special episode of Sabrina the Teenage Witch. Melissa: “You’re always surrounded by people!” Britney: “Sometimes that’s the loneliest place to be.” No kidding.

Play video

Youtube

28

‘Kill the Lights’ (2008)

B goes hard in revenge mode, a fantasy of punching out papparazzi and going all Don Barzini on their cameras, screeching, “I kiiiiiill the lights!” It begins with a quote from the infamous 1938 War of the Worlds radio broadcast that panicked America into thinking it was a real Martian invasion: “Ladies and gentleman, we interrupt our program of dance music to bring you a special bulletin!” In other words, “Kill the Lights” is the first Britney song that has Orson Welles as a co-writer, though you could argue she lived out Citizen Kane. 

Play video

Scott Gries/Getty Images

27

‘(I Can’t Get No) Satisfaction’ (2000)

Let it bleed, Britney. Our girl is an absolute genius at sacrilegious cover versions, and “Satisfaction” is her boldest, vandalizing the Rolling Stones and making her own claim on the rock & roll hell-raising tradition. You would not believe how mad boomer dudes got over this, but her arrogance is worthy of Mick Jagger himself. She twists the line “how white my shirts could be” into “how tight my skirt should be,” snarling in libidinal frustration. It’s only rock & roll, but she likes it. 

Play video

David Becker/Invision/AP

26

‘Work Bitch’ (2013)

Her love song to the hustle, chanting “You better work, bitch!” over a bitch-perfect tinsel-disco beat. She barks dominatrix commands in her finest Kensington-via-Kentwood accent, like the warden in a low-budget women’s-prison flick. Like so many of her hits, “Work Bitch” adds up the high costs of stardom, but it all just makes her greedier for more. 

Play video

Kevin Mazur/WireImage

25

‘Mona Lisa’ (2005)

“Mona Lisa” is a deep cut that only the most hardcore fanatics know — from the bonus CD that came with the Britney & Kevin: Chaotic DVD. But it’s one of her toughest, darkest comments on stardom. She co-wrote it with her live band, sounding pissed-off, in a “Lucky” sequel that begins, “This is a story about Mona Lisa.” But this Mona Lisa is a clone who hides behind her smile and plots her rebellion. She dishes the dirt about celebrity: “I’ve got a little story to tell / About Mona Lisa and how she suddenly fell… / Now I am taking over to release her from her spell!” No wonder the label didn’t want to release it. Britney previewed the song on Ryan Seacrest’s L.A. radio show in 2004, dedicating it to “the legends and icons out there.” It might be the most autobiographical thing she’s ever done, with lines like, “Everyone’s watching as she starts to fall.” Britney at her rawest and realest—a taste of her mythical lost album Original Doll.

Play video

Chris Weeks/WireImage

24

‘Hot as Ice’ (2007)

Britney was born the year Rick James ruled the radio with “Super Freak,” so it’s fitting she nails this tribute, starring as the kind of girl you read about in New Wave magazines. “Hot as Ice” is the most expert Rick James clone job since Cameo did “Word Up,” with Danja doing his nasty I’m-Rick-James-bitch background vocals. But it sounds totally Britney. “This ain’t no foolishness or fuckery,” she declares — spoken like a girl who wants to party all the time. 

Play video

Youtube

23

‘Sometimes’ (1999)

The great forgotten Britney hit. “Sometimes” was her her all-important second single, after “…Baby One More Time” put her on the map. Keep in mind, this was the summer of 1999, the all-time peak of one-hit wonders — back then, going from one hit to two was even tougher than the jump from zero to one. “Sometimes” was the hit that gave her a career. And much more than the debut single, “Sometimes” invented her image as the all-American teen queen of TRL Nation. (“I don’t wanna be so shy / Everytime that I’m alone I wonder why”—way too relatable.) She also introduced her trademark video move of rolling her eyes up at the camera. Ariana Grande clearly studied this video like a chess master studying Bobby Fischer. Blink-182 built a career on making fun of it. The video also has an all-time peak for MTV cheese: While Brit feels her feelings, her elfin dancers surround her on the pier in the shape of a heart. 

Play video

Youtube

22

‘Criminal’ (2011)

She’s got something to confess, Mama — she’s in love with an evil outlaw who’s got no conscience (“None! None! None! None!”) and no heart. But anyone can hear that Brit is the “Criminal” she’s singing about. This Femme Fatale highlight is a bizarre Ray Davies pastiche, with a Village Green Preservation Society-style flute/guitar playing the melody from the Kinks classic “I’m Not Like Everybody Else.” How does she get away with crazy shit like this? Because she’s not like everybody else.

Play video

Al Powers/Powers Imagery/Invision/AP

21

‘Alien’ (2013)

The Bowie-Britney connection runs deep. It’s crazy how much these two extraterrestrial pop voyagers have in common — the Blondes Who Fell to Earth. “Alien” is a lonely space-girl ballad where Major Britney floats across the galaxy, looking for a planet where she might finally feel at home, over William Orbit synth bleeps. “I always felt like a stranger in a crowd,” she sings, her sad-robot voice filtered through layers of cosmic dust.