This article has been updated.
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.
19. "Work B***h"
Hot 100 Peak Position: 12 (2013)
"Work B***h," the lead single off Britney's eighth studio effort Britney Jean, peaked at 12 on the hot 100 and told fundamental truths -- if you want to look like Britney, drive like Britney and be as successful as Britney, you better work, b---h.
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.
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 her album 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.
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.
Hot 100 Peak Position: 15 (2004)
This breathy ballad came after her breakup with Justin Timberlake and rumors quickly swirled that this Britney Spears 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, b---h," 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.
10. "Oops!...I Did It Again"
Hot 100 Peak Position: 9 (2000)
After her debut album made her a bubblegum pop star, Spears declared, "I'm not that innocent" on the title cut to her sophomore album. "Oops" will forever be remembered as the song Spears performed at the MTV VMA's in a risque, skin-colored outfit.
Hot 100 Peak Position: 9 (2004)
For the second single off 2004's In the Zone, Britney went with something a little different, sonically-speaking. "Toxic" went to places previously unexplored by Spears: aggressive electronic sound effects, shrieking strings and a killer surf-guitar riff. The unlikely combo, ushered in by steamy vocals, worked, as "Toxic" burned into the Hot 100's top 10.
8. "Hold It Against Me"
Hot 100 Peak Position: 1 for one week (2011)
This pulsating dance track with its thickly-layered production (via Max Martin, Dr. Luke and Billboard), a pickup-line chorus ("If I said I want your body now ...") and a dubstep-ish breakdown debuted in January 2011 atop the Hot 100 and made Britney only the second artist to launch a song at No. 1 multiple times. The lavish and futuristic video, which contains a Fight Club-esque scene where Brit battles Brit, helped to make "Hold It Against Me" -- and her platinum-selling album Femme Fatale -- the huge hits they are.
7. "I Wanna Go"
Hot 100 Peak Position: 7 (2011)
Who says Brit shouldn't do what she wants? On this cut from Femme Fatale, it's clear that when she just lets go of her inhibitions and cuts loose, she's capable of making hot dance jams and top 10 hits. This happens to be both.
Hot 100 Peak Position: 3 (2008)
"There's only two types of people in the world. The ones that entertain and the ones that observe," is the lead line of Britney's "Circus." We've known which one she is -- the lady in the limelight -- since her debut single. This title track of her sixth album reinforces that, marking a return to the straight-forward pop sound for which she became known in her early days.
5. "Til The World Ends"
Hot 100 Peak Position: 3 (2011)
"Hold It Against Me" may have been the lead single to Femme Fatale, but its follow-up, "Til The World Ends," captures the essence of Spears' electro-pop opus. The track was a Hot 100 hit even before fellow pop divas Nicki Minaj and Kesha joined Brit for a remix.
Hot 100 Peak Position: 1 for one week (2009)
A single from her 2009 Singles Collection package, "3" is the combination of several Britney signature styles. Mainstream pop is certainly in the forefront, lustful moans on the chorus and a touch of electronic is also in the mix. The title, meanwhile, may be seemingly innocent, but it actually refers to something quite less so. Fun fact: this Britney Spears song is 3:33 long.
3. "Scream & Shout" - Will.i.am & Britney Spears
Hot 100 Peak Position: 3 (2013)
Featuring a dark, slithering beat and a slew of club commands, "Scream & Shout," from Will.i.am's album Willpower, features a very different look for Spears, whose voice is roboticized to a nearly unrecognizable degree. "I wanna scream, and shout, and let it all out," Spears and will.i.am sing in unison on the chorus, before the pop star drops a signature "Britney, b---h" and the percussion is dutifully ratcheted up.
Hot 100 Peak Position: 1 for one week (2008)
With a tumultuous 2007 behind her, Britney knew she needed a big year in music to come back from all the tawdry drama. With "Womanizer," from Circus, she was able to do just that, and score her first No. 1 on the Hot 100 since "...Baby One More Time."
1. "...Baby One More Time"
Hot 100 Peak Position: 1 for two weeks (1999)
Britney's debut single, "...Baby One More Time," remains her biggest hit, undoubtedly fueled by its sexy schoolgirl music video. The Max Martin-penned single sustained a steady build, ruling the Hot 100 chart at No. 1 for two weeks in early 1999 after debuting on the chart in late November '98, a month after it was serviced to radio and just a few weeks shy of her 17th birthday.
Text by Jeff Benjamin, Keith Caulfield, Michael Depland, Jason Lipshutz, Jillian Mapes, Erika Ramirez and Marc Schneider.
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 Dec. 5, 2020. 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.