Britney Spears has already left her mark on the music industry (the whole world, really) with her string of memorable chart-topping hits. From the infectious pop anthems that dominated the airwaves to the iconic music videos that became cultural touchstones, Spears has consistently delivered an unparalleled level of success.
However, amidst her chart-conquering triumphs, there exists a collection of songs that, despite their brilliance, failed to make a significant impact on Billboard’s Hot 100. These hidden gems represent some of Spears’ most compelling and daring musical moments, and they shine a light on her artistic evolution and demonstrate that commercial success does not always dictate artistic quality.
Let’s dive into Spears’ most underrated singles that somehow missed the Hot 100 entirely. Hopefully we provide at least a little bit of justice for these bangers.
“Don’t Let Me Be the Last to Know”
“Don’t Let Me Be the Last to Know” is one of Spears’ earliest pop ballads, released as the fourth single from her sophomore album, Oops!… I Did It Again in 2001. The song showcases her vulnerable and heartfelt side, which the world doesn’t see or hear very often.
By the time it was released as a single, Spears was already a global sensation, well on her way to being a certified pop icon. While “Don’t Let Me Be the Last to Know” may not have received the recognition it deserved at the time, it serves as a testament to the singer’s ability to deliver emotionally resonant performances amidst her larger-than-life pop persona.
“I’m Not a Girl, Not Yet a Woman”
The oddly-titled “I’m Not a Girl, Not Yet a Woman” is yet another ballad by the star. This poignant and introspective tune was chosen as the second single from her third studio album, the self-titled Britney.
She dropped the cut in 2002, and it reflects her transition from her teenage years to adulthood. Despite being critically acclaimed for its emotional depth and Spears’ heartfelt vocals, the track didn’t achieve substantial chart success, and it missed out on the Hot 100. That was odd, as most tracks she shared around that time became hits, and it came not long after the still-insanely catchy “I’m a Slave 4 U.”
“Boys” (ft. Pharrell Williams)
Spears released more than one version of “Boys,” as they were used for different purposes. The original, featured on her album Britney, sees the singer owning the track all on her own. Another take features the tune’s songwriter and producer Pharrell Williams, who was then working as one-half of The Neptunes. That edition was known as The Co-Ed Remix, and it was found on the Austin Powers in Goldmember soundtrack. It’s inclusion on that CD made sense, as Spears herself had a fun cameo in the picture, so of course there was some music from the star in there as well.
Despite the many major stars attached to the cut and the fact that it was heard in a summer blockbuster, “Boys” wasn’t a huge commercial success as many predicted it would be.
Originally recorded by Bobby Brown in 1988, Spears’ rendition of “My Prerogative” adds a contemporary pop flavor to the iconic track. Released in 2004 as the lead single from her first greatest hits compilation of the same name, the song showcases Britney’s fierce and unapologetic attitude. The reworking was not appreciated in its time, and the compilation’s follow-up promotional cut “Do Somethin’” didn’t fare much better, as it only reached No. 100 on the Hot 100.
Around the time of its release, Spears was facing intensified media scrutiny and personal challenges, making “My Prerogative” the powerful anthem of self-assertion that she needed at the time.
“Tom’s Diner” (Giorgio Moroder featuring Britney Spears)
Another cover that the world didn’t give its flowers! A collaboration with Grammy and Oscar-winning producer Giorgio Moroder, “Tom’s Diner” was taken from his also criminally-overlooked album Déjà Vu. The two knew they wanted to work together on something, and according to Moroder, the idea to remake the classic hit originally performed by Suzanne Vega was Spears’ and hers alone.
The updated take on the ‘90s classic showcased Spears’ versatility as an artist, venturing into the realms of electronic music while maintaining her pop sensibilities. It took what people knew about “Tom’s Diner” and made it sound brand new, like nothing anyone had heard from either artist before. It is still relatively unknown, but it deserves the world.
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