Britney Spears has been a pop icon since she was a teenager. Such notoriety from such an early age can be difficult to weather, and she has often had to fight her private battles in the public eye. But she has put together a pretty remarkable body of work in spite of those challenges. Below we count down her 30 greatest hits. What do you think of our choice for her number-one of all time?
30. “Work Bitch” (2013)
29. “Make Me” featuring G-Eazy (2016)
28. “Pretty Girls” with Iggy Azalea (2015)
27. “Perfume”(2013)
26. “Piece of Me” (2007)
25. “I Wanna Go” (2011)
24. “Don’t Let Me Be the Last to Know” (2001)
23. “Gimme More” (2007)
22. “From the Bottom of My Broken Heart” (1999)
21. “Hold It Against Me” (2011)
20. “Everytime” (2004)
19. “Me Against the Music” featuring Madonna (2003)
18. “Break the Ice” (2008)
17. “Lucky” (2000)
16. “Overprotected” (2002)
15. “Circus” (2008)
14. “Sometimes” (1999)
13. “If You Seek Amy” (2009)
12. “Scream and Shout” with will.i.am (2012)
11. “Womanizer” (2008)
10. “Boys” featuring Pharrell Williams (2002)
9. “I’m Not a Girl, Not Yet a Woman” (2002)
8. “3” (2009)
7. “I’m a Slave 4 U” (2001)
6. “Oops! I Did It Again” (2000)
5. “Till the World Ends” (2011)
4. “(You Drive Me) Crazy” (1999)
3. “… Baby One More Time” (1998)
2. “Stronger” (2000)
1. “Toxic” (2004)
Spears was signed to a record deal when she was just 15-years-old, and her debut single, “… Baby One More Time,” hit number one on the Billboard Hot 100 when she was barely 17. What’s more, she rose to fame in the late 1990s when there was a revolution of teen superstars achieving astronomical record sales. Her first two albums, “… Baby One More Time” (1999) and “Oops! … I Did It Again” (2000), were both certified diamond with US sales exceeding 10 million copies, with the earlier going 14-times platinum.
Her first seven albums all went platinum, though not without growing pains along the way. She became a target of tabloid gossip in the 2000s, due in no small part to her relationship with fellow teen pop star Justin Timberlake. She endured a mental health crisis that made her the butt of media jokes, and she was subsequently placed under a conservatorship overseen by her father that greatly restricted her ability to make choices in her life and career.
The 2021 documentary “Framing Britney Spears” brought to light her struggles and led to a reevaluation of her life and career, including the media’s role in persecuting her and other young female stars who find themselves torn down by tabloids. That strengthened the #FreeBritney movement that sought to bring attention to her conservatorship in the hopes of winning her back her autonomy.
Despite her struggles, though, she has managed to produce some of the most indelible dance-pop hits of the last 25 years, including the song we rank as her very best, “Toxic,” which won her a Grammy for Best Dance Recording. So let’s celebrate her artistry as well as her fight for her freedom.
