If you think about it, Britney Spears is one of the last pop stars created during the “old” era of the music industry (meaning, before the advent of mp3’s). Her career as a bubblegum teen idol was launched in the late nineties, right at the same time as a little show on MTV called TRL was beginning to take off. The fortunes of these two properties became inextricably tied together, and thanks to some crazy catchy tunes and some truly iconic music videos that got tons of on-air exposure during the last gasp of MTV’s infatuation with the music video format, Britney Spears quickly became not only the biggest star in the music industry, but one of the most famous celebrities in all the world.
As everyone knows, her tabloid notoriety would soon go on to eclipse her musical output, and there was a period of time there when a lot of people thought that Britney Spears might not make it to her 30th birthday. However, to her credit, Britney was able to pull her life back together and re-dedicate herself to her music career, and her focus is now unquestionably sharp. As we look back upon her body of work on the occasion of Brit Brit’s milestone 30th birthday—an incredible six Number One albums, nineteen Top 40 singles (!)—it’s a testament to her longevity and outstanding career output that we had an incredibly difficult time putting together this list of the 30 Greatest Britney Spears Songs (which you can also listen to on Spotify).
Feel free to debate our choices in the comments below!
30. “Radar” (Blackout, 2007)
29. “If You Seek Amy” (Circus, 2008)
28. “Hot As Ice” (Blackout, 2007)
27. “Showdown” (In The Zone, 2003)
26. “Break The Ice” (Blackout, 2007)
25. “Soda Pop” (Baby One More Time, 1999)
24. “Hold It Against Me” (Femme Fatale, 2011)
23. “Overprotected” (Britney, 2001)
22. “(I Got That) Boom Boom” (In The Zone, 2003)
21. “How I Roll” (Femme Fatale, 2011)
Keep reading for the Top 20!
20. “Don’t Let Me Be The Last To Know” (Oops!… I Did It Again, 2000)
19. “Piece Of Me” (Blackout, 2007)
18. “I’m Not A Girl, Not Yet A Woman” (Britney, 2001)
17. “Lucky” (Oops!… I Did It Again, 2000)
16. “Circus” (Circus, 2008)
15. “Born To Make You Happy” (Baby One More Time, 1999)
14. “I Wanna Go” (Femme Fatale, 2011)
13. “Sometimes” (Baby One More Time, 1999)
12. “Me Against The Music (feat. Madonna)” (In The Zone, 2003)
11. “(You Drive Me) Crazy (The Stop Remix)” (Oops!… I Did It Again, 2000)
10. “Gimme More” (Blackout, 2007)
It’s Britney, bitch! This was Britney’s comeback song after her infamous meltdown, the one that she famously sleptwalk through during a particularly disastrous performance at the 2007 VMAs. However, now that we’re a few years removed from the tabloid drama of these days, the song holds up as a dancefloor classic.
9. “Womanizer” (Circus, 2008)
Britney’s 2007 album Blackout was positioned as her “comeback” album, but she made her real comeback with 2008’s Circus. “Womanizer,” the first single off that album, is a hypnotic and swirling banger produced by The Outsyders and features, arguably, the catchiest chorus in her outstanding body of work.
8. “Everytime” (In The Zone, 2003)
The video for “Everytime,” which featured Britney Spears facing off against Stephen Dorff and attempting suicide, became tragically poignant during her mid-Aughts meltdown phase. However, as a song, it’s far and away her the most moving ballad, largely because she puts her voice out in front of the mix for one of the few times in her career. Anyone who accuses Britney of not being able to sing has clearly never heard this song.
7. “Till The World Ends” (Femme Fatale, 2011)
Ever since the outset of her career, Britney’s music has always followed the course of the times, from the bubblegum pop of the late nineties to the Neptunes-sound that dominated the early 2000s to today’s Euro-driven house beats. “Till The World Ends” features some incredibly of-the-moment production by Dr. Luke, and pairs her once again with Max Martin, the man whose songs shot Britney to stardom back in the fall of 1998.
6. “Boys” (Britney, 2001)
Britney teamed up with Chad Hugo and Pharrell Williams of the Neptunes for this Prince-inspired sextastic superjam. The groove is undeniably slinky, and Britney’s voice is full purr-kitty mode. Only an ill-conceived bridge keeps this song from sitting even higher on this list.
5. “Stronger” (Oops!… I Did It Again, 2000)
Confession: whenever things are going pear shaped in our lives, we dim the lights, pull out a chair, and alone in our bedrooms we’ll blast “Stronger” while attempting to emulate Britney’s chair dance-battle. TMI? We don’t care — “Stronger” was Britney’s stand against the generally sappy sentiment in … Baby One More Time and became somewhat of a girl power anthem at the time of its release on her second album Oops!… I Did It Again. Also, did we mention the awesome chair dance-battle in the video?
4. “Oops!… I Did It Again” (Oops!… I Did It Again, 2000)
Everything about “Oops!… I Did It Again” is completely unforgettable pop magic. Everything from the cheesy space-scape video to Britney’s red pleather jumpsuit, long, high pony tail and punchy chorus is definitive to millennial pop. In 2000, “Oop!” tread the line between the future with a tongue-in-cheek dialogue referencing Titanic and the past carrying over what was left of earnestness from the 90s. Looking back now, there’s an irony in the line “I’m not that inoccent,” given how innocently the visual and lyrical sentiment seems by comparison to Britney’s later work.
3. “I’m A Slave 4 U” (Britney, 2001)
While Britney claimed “I’m A Slave 4 U” was about being a slave to the music, the video and heavy innuendo in the lyrics would suggest something a little bit more naked. The sexy track was part of Britney’s post-teen rebellion, her “finding herself” phase, and if you ask us, it’s the kind of song that would still fit neatly into the music landscape now, albeit with a bit of tweaking to the uber-hipster jean costuming in the video. Our challenge to you is to just try not to dance while listening to “Slave,” because we bet you can’t (toe tapping and shoulder jiggling counts).
2. “Toxic” (In The Zone, 2003)
From her fourth album, In The Zone, “Toxic” is one of Britney’s best, most catchy songs — a pop classic if you will. “Toxic” proved that, even four albums in, Britney still reigned supreme as pop princess, and wasn’t about to be toppled from her throne. Also let’s just mention the part in the video where she’s rolling around in a mirror room wearing nothing but a handful of sparkly diamond-like jewels across her body. Part of Britney’s prolonged sexual awakening and the prologue to her “Not A Girl, Not Yet A Woman” phase, “Toxic” was the icing on Britney “growing up.” And what tasty icing!
1. “…Baby One More Time” (Baby One More Time, 1999)
Ordering this list wasn’t easy, because Britney’s hits are generally of equal greatness. So it stands to reason that the first hit should be the best. “…Baby One More Time” introduced to the world to the 16-year-old all American girl with an overexposed midriff, a dangerously tiny skirt and pom-poms in her hair. The track wasn’t just seminal to Britney’s career, it’s become one of the most iconic pop songs (and videos) of the past 20 years. And oh yeah, we definitely learned the whole hallway-scene dance from the video when it was released, but no, we don’t remember it (except that we totally do and we’re doing it right now).
Happy birthday, Britney!
Remember, you can listen to this entire playlist on Spotify: VH1 Presents: The 30 Greatest Britney Spears Songs