#10 “Hold It Against Me” – Femme Fatale (2011)
As a single person, all I want in my life is for someone to sing to me: “You feel like paradise… and I need a vacation tonight.” It’s a spectacularly low-bar, but no one has cleared it yet.
#9 “Piece of Me” – Blackout (2007)
Britney’s most explicitly personal song to date dramatically benefits from the massive vocal tuning, showing the distance between the listener, her fans, the general public, and the “real” Britney. This song works on a lot of levels.
#8 “Don’t Let Me Be the Last to Know” – Oops!… I Did It Again (2000)
My favorite Britney ballad. Baby Britney blesses us with a great vocal filled with longing and yearning – the two -ings every great ballad requires. Written by Shania Twain!
#7 “(You Drive Me) Crazy” – …Baby One More Time (1999)
Obviously, the 7th greatest Britney Spears song is from the 1999 Melissa Joan Hart-Adrian Grenier film, Drive Me Crazy. The version where Britney says “STOP!” so authoritatively, she shifted my entire body chemistry and the tectonic plates of the Earth’s very core in the process?
#6 “Make Me…” – Glory (2016)
A controversial pick to place so highly. The lead single from Britney’s most recent release is gorgeous, a significant return to form, vocally, sonically from Britney Jean. I think we can all agree this should have immediately shot directly to number one on every chart and remain there currently.
#5 “Shattered Glass” – Circus (2008)
Much like Taylor Swift’s All Too Well, this is a non-single track considered by many to be Britney’s finest hour. So beloved, in fact, that, despite never being formally released, it still made it all the way to number 70 on the Billboard Hot 100.
#4 “Stronger” – Oops!… I Did It Again (2000)
Early era Britney is filled with empowerment songs, and this is the brightest of the bunch by a mile. The best key change of her career. Solid chair-choreo in the video, a perennial favorite.
#3 “Toxic” – In the Zone (2003)
Britney, as a video artist, is yet another aspect of her career in which she is undervalued. “Toxic” is her most significant, most cinematic music video, with imagery so influential it made everyone want a diamond-encrusted sheer bodysuit and Martin Henderson of their very own.
#2 “Till the World Ends” – Femme Fatale (2011)
If “…Baby One More Time” was Britney’s undeniable cultural impact moment, I’d argue “Till the World Ends” is her best absolute banger. Immediately, I want to be in “the club,” feet sticking to the ground, the faint smell of spilled vodka soda on my arm from dancing too hard.
#1 “…Baby One More Time” – …Baby One More Time (1999)
I think we can all agree the term ‘iconic’ or ‘cultural reset’ is being thrown around pretty haphazardly these days. That said: “…Baby One More Time” was an iconic cultural reset. Hard stop. For older millennials (anyone who was 7 to 17 before the turn of the millennium), the drop of this song, album, video was the defining musical event of our generation. Bold words, but think about it: What else compares to the bing bong bing that kicks things off, the schoolgirl uniform, the absolute madness surrounding all of it. Yes, there were boy bands, but no singular event from Backstreet Boys or NSYNC compared to the seismic shift in The Culture when Britney burst onto the scene with this, her first single.
On a personal note, if I could’ve figured out what the dueling desire for Britney and to learn the choreo from this video meant in 1999, I really could’ve saved myself a lot of time and therapy.