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In Billboard Staff’s cumulative ranking of Britney Spears’ 20 biggest Billboard hits, “…Baby One More Time” is No. 1. The list weighs a song’s performance across its Hot 100 chart run, rather than ranking songs only by their highest position. It covers chart weeks through the Billboard Hot 100 dated December 5, 2020, so it is a historical ranking—not a verified 2026 recalculation.
How Billboard ranked the hits
Billboard Staff’s December 2, 2020 feature ranks the songs by cumulative performance on the weekly Billboard Hot 100. Its inverse-point system awards more points for a week at No. 1 than for a week at No. 100. The order therefore reflects chart performance over time, not simply each song’s peak. Billboard Staff’s ranking, republished by Radio 88.8, ends with the chart dated December 5, 2020.
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Britney Spears’ 20 biggest Hot 100 hits
The order below reproduces that 2020 cumulative ranking. The peak is the song’s highest reported Hot 100 position; it is not its ranking score.
| Rank | Song | Hot 100 peak |
|---|---|---|
| 1 | “…Baby One More Time” | No. 1 for two weeks (1999) |
| 2 | “Womanizer” | No. 1 for one week (2008) |
| 3 | “Scream & Shout” (will.i.am featuring Britney Spears) | No. 3 (2013) |
| 4 | “3” | No. 1 for one week (2009) |
| 5 | “Til The World Ends” | No. 3 (2011) |
| 6 | “Circus” | No. 3 (2008) |
| 7 | “I Wanna Go” | No. 7 (2011) |
| 8 | “Hold It Against Me” | No. 1 for one week (2011) |
| 9 | “Toxic” | No. 9 (2004) |
| 10 | “Oops!…I Did It Again” | No. 9 (2000) |
| 11 | “Gimme More” | No. 3 (2007) |
| 12 | “(You Drive Me) Crazy” | No. 10 (1999) |
| 13 | “Everytime” | No. 15 (2004) |
| 14 | “If U Seek Amy” | No. 19 (2009) |
| 15 | “Piece Of Me” | No. 18 (2008) |
| 16 | “Sometimes” | No. 21 (1999) |
| 17 | “Stronger” | No. 11 (2001) |
| 18 | “From The Bottom Of My Broken Heart” | No. 14 (2000) |
| 19 | “Work B***h” | No. 12 (2013) |
| 20 | “Lucky” | No. 23 (2000) |
Why peak position and “biggest hit” are not the same
A peak records a single best week; the cumulative ranking considers performance across a chart run. That distinction explains why “Oops!…I Did It Again” and “Toxic” can each peak at No. 9 while landing at different places in the overall list. The same list places “I Wanna Go,” with a No. 7 peak, above “Hold It Against Me,” which reached No. 1 for one week.
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Which songs reached No. 1?
Four entries in this ranking reached the top of the Hot 100: “…Baby One More Time” spent two weeks at No. 1, while “Womanizer,” “3,” and “Hold It Against Me” each spent one week there. Billboard Staff’s list ranks “Womanizer” second overall, although “…Baby One More Time” had the longer No. 1 run. GRAMMY.com also describes “Womanizer” as Spears’ return to No. 1 in 2008: GRAMMY.com’s chart-history account.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.What the ranking does—and does not—establish
This is a US Billboard Hot 100 ranking using the chart data available through December 5, 2020. It should not be presented as a current 2026 order: no authoritative newer cumulative recalculation is established here. Hot 100 peak positions also should not be confused with album or chart performance in other countries.
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For a separate snapshot of “Oops!…I Did It Again,” GRAMMY.com reported its Hot 100 peak as No. 9 in 2024: GRAMMY.com on the song and album. That corroborates the peak, but does not update the cumulative ranking.
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