Britney Spears' 20 Biggest Billboard Hits
Randee St. Nicholas

Britney Spears was just 16 years old when she made her debut on the Billboard Hot 100 singles chart on Nov. 21, 1998 with the now classic "... Baby One More Time." The song shot to No. 1 less than two months later and the rest was history. Since then, she's had a single on the chart every year (save for 2006) and has recently found the some of the biggest hits of her career. Her "Femme Fatale" album, which debuted at No. 1 on the Billboard 200 chart, has launched three top 10 Hot 100 singles, including the No. 1 "Hold It Against Me," and 2013 saw her track with Will.i.am climb the charts

To celebrate Spears, we've compiled her 20 Biggest Billboard Hot 100 hits ever.

This chart of Spears' 20 Biggest Billboard Hot 100 Hits is based on actual performance on the weekly Billboard Hot 100, through the chart dated Sept. 21, 2013. Songs are ranked using an inverse point system, with weeks at No. 1 earning the greatest value and weeks at No. 100 earning the least.

Photos: Britney Spears's 35 Most Outrageous Outfits

20. "Break The Ice"
Hot 100 Peak Position: 43 (2008)
The icy synth track, produced by Danja, found Ms. Spears singing, "I know it's been a while, but I'm glad you came." She was only half right. It had only been a few months since she rocketed to No. 3 on the Hot 100 with "Gimme More," but we're sure she was glad fans flocked to the tune despite the distraction of all the tabloid drama that surrounded her in the year before the song hit the charts in 2008. It's little wonder the real Britney doesn't appear in the animated video.

19. "Lucky"
Hot 100 Peak Position: 23 (2000)
Britney's midtempo nod to doo-wop, "Lucky," turned out to be less than pure fiction when the singer later went through personal problems in the very public eye. But before all that, in 2000, the song -- a take on the "lonely at the top" concept -- peaked at No. 23 on the Hot 100.

 

18. "From The Bottom Of My Broken Heart"
Hot 100 Peak Position: 14 (2000)
Still a teenager when this Eric Foster White-produced single was released in 2000, Spears' convincing take on love lost helped "Broken Heart" reached the top 20 of the Hot 100.

 

17. "Stronger"
Hot 100 Peak Position: 11 (2001)
Brit Brit kicked the potential sophomore slump to the curb with one of her best songs of female empowerment. The dance-y "Stronger," off "Oops!... I Did It Again" not only hit the Hot 100 hard, it also landed in the top 20 of the Pop Songs radio airplay chart.

16. "Sometimes"
Hot 100 Peak Position: 21 (1999)
"Sometimes," Spears' second single, epitomizes the innocence of the pop star's first album, especially in its sunny music video. Wearing all white, Spears and her dancers overtake Kenny's Cove and perform some unoffending dance moves while the singer yearns for her hunky man.

15. "Piece Of Me"
Hot 100 Peak Position: 18 (2008)
"Miss American Dream since [she] was 17" addresses her harshest critics in this woozy synth hit. Clearly, we did want a piece. In addition to its top 20 peak on the Hot 100, it went to No. 8 on the Digital Songs chart and won her the MTV Video Music Award for Video of the Year in 2008.

14. "If U Seek Amy"
Hot 100 Peak Position: 19 (2009)
The third single from her comeback album, "Circus," captures Britney playing bad girl. (Say the title fast). The 2009 track finds Spears singing of society's perception of her life over electro-pop synthesized beats.

13.  "Everytime"
Hot 100 Peak Position: 15 (2004)
This breathy ballad came after her break-up with Justin Timberlake and rumors quickly swirled that her song was a response to his "Cry Me a River." Although Brit has never denied or confirmed, the lyrics are certainly curious. "I may have made it vague," she sings. "Please forgive me. My weakness caused you pain. And this song is my sorry."

12.  "(You Drive Me) Crazy"
Hot 100 Peak Position: 10 (1999)
"Crazy" snuck into the top 10 of the Hot 100 as the third single off "... Baby One More Time" and the lead cut from the soundtrack of the 1999 romantic comedy "Drive Me Crazy," starring Melissa Joan Hart and a pre-"Entourage" Adrian Grenier in his first major role.

11. "Gimme More"
Hot 100 Peak Position: 3 (2007)
When a song begins with "It's Britney, bitch," you just know you're in for a treat. The fact that "Gimme More," Spears' lead single off 2007's "Blackout," wasn't very appetizing to critics didn't matter to fans, who helped send the breathy, stripper-ready dance track to No. 3 on the Hot 100 in October of that year. However, it was Brit's embarrassing performance of the song on the MTV VMAs a couple weeks before its release that has endured and in its wake spawned an early YouTube star in Chris "Leave Britney Alone!" Crocker.

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Text by Jeff Benjamin, Keith Caulfield, Michael Depland, Jason Lipshutz, Jillian Mapes, Erika Ramirez and Marc Schneider

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