#30 “Criminal” – Femme Fatale (2011)
This song re-entered the Billboard Hot 100 in 2020, thanks to the Mugshot Challenge on Tik Tok. I only know what the first half of that sentence means, but I love this song.
#29 “3” – The Singles Collection (2009)
The lyrics to this #1 hit on the Billboard Hot 100: One, two, three / Not only you and me / Got one eighty degrees / And I’m caught in between. I’m just a simple boy who believes that is cause for celebration..
#28 “Shadow” – In The Zone (2003)
A song about a lover who is emotionally gone. Or a song about Peter Pan’s complicated relationship with his projection of himself. Either way one of her best, most expansive vocals.
#27 “Let Me Be” – Britney (2001)
To the paparazzi who, in Framing Britney Spears said Britney never really told him to leave her alone: She was writing songs called Let Me Be with the continued refrain “I won’t turn around” since 2001, you asshole.
#26 “Do Somethin’” – Greatest Hits: My Prerogative (2004)
Successfully makes me want to look across the dance floor at the other drunk gay at the wedding and have the dance-off everyone has been dreading. The moves are terrible, but the song is a banger.
#25 “Heaven on Earth” – Blackout (2007)
Ranking this disco opus, one of Britney’s most sonically interesting, in the Top 25, is my formal request for a Jessie Ware collaboration. Please and thank you.
#24 “My Only Wish (This Year)” – Platinum Christmas (2000)
One of the best Christmas songs this century, hard stop. We should be discussing this one the big ones: “All I Want for Christmas is You,” “Underneath the Tree,” whatever that Michael Bublé song is. This shouldn’t even be a controversial statement.
#23 “Everytime” – In the Zone (2003)
Safe to say that this is Britney’s prettiest song, right? Loses a few spots for being just this side of boring, but it is one of the best showcases for her lilting voice. Written by Ms. Spears, her damn self, for all the music snobs who think the Glen Hansard version is superior.
#22 “Womanizer” – Circus (2008)
The full-on chart dominance that Blackout was supposed to usher in happened with “Womanizer,” Britney’s first #1 song on the Hot 100 since …Baby One More Time.
#21 “Lucky” – Oops!… I Did It Again (2000)
I love this song because it’s the first time (but not the last time) Britney explicitly plays a part, telling a story via song. She’d do this again throughout her career, but never more successfully than with Academy Award-winning actress (!) Lucky!