The Best Britney Spears Songs? This YouTube Playlist Weighs In

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Jive / Background: Eclectic Pop

Britney Spears has had so many hit songs that it is hard to declare which is her best. Few artists can boast two great songs, let alone one. For Britney Spears, hits have come repeatedly. During the 2000s, Spears led the top of a competitive pack of pop singing sensations thanks to her one-of-a-kind anthems. And like many fans, I have 27 favorites that I consider the best, and they are in this YouTube playlist:

Last year, it had been on my heart to curate a playlist of Britney Spears’s best songs. The idea came after putting together a playlist of Taylor Swift’s best love songs, followed by her best songs ever. A year later, a look back at Britney Spears’s best songs has taken on new relevance as talk surrounding her personal life has hit another high. Lest we forget the incredible songs that made her a household name in the first place.

Remember, Britney Spears Is An Icon

Before Britney Spears became news fodder as a person, she was mainly known to the world as one of the preeminent pop stars in the universe. Spears’ rendition of bubblegum pop was unlike anyone else’s, even though they tried hard. Her skills as a concert performer put her over the top. Spears’ performances at awards shows were legendary. However, while curating this playlist of Spears’ best songs, I realized something.

Britney Spears’ music is not just iconic because of its hit status. Nor is it that it is just as catchy as the day listeners first heard it. Britney Spears’ sound was and is uniquely hers. The music represents an enigmatic figure capable of many musical roles that all seem to magically fit her. From “Baby One More Time” to “Criminal,” Spears has never backed down, her tongue neatly pressed against her cheek.

It is fair to say that she has been the iron fist in a velvet glove. No one has been able to pin down who Britney Spears is except as a music artist. Spears is known for her catchy hooks, multi-meaning lyricism, and power-pop melodies that make for tasty ear candy. None of her songs have grown tiresome with time. Instead, they have proven timeless.

As you will see in the playlist, the third time was the charm for Britney Spears. Now, some fun factoids. First, Spears’ third studio album, the semi-self-titled ‘Britney,’ has the most entries on this playlist. Second, as some fans may know, Britney Spears proved she was not just the face of the music but a key player behind it. Spears co-wrote five songs on the album, including “Lonely” and “Cinderella.” 

Yes, it turns out that Britney Spears may have more in common with Taylor Swift than their zodiac sign (Sagittarius), a global celebrity, speaking during songs (“Dear Diary”/ “We Are Never Ever Getting Back Together”) and the media’s similar coverage of them. If Spears had not overcome what she did, who knows if Swift would have been able to reinvent herself so many times.

Circa 2021, the Britney Spears song that resonates the most is “Lucky.” The single off of Spears’ sophomore album ‘Oops I Did It Again’ tells the story of the eponymous, Lucky, a celebrity with everything and nothing at the same time. In 2000, it felt telling, insightful, and possibly autobiographical. Cut to 2021, and the lines between the music get blurry.

Britney Spears Paved The Way

Unlike Taylor Swift, none of Britney Spears’ songs got truly billed as representative of the actual “Britney.” Instead, they were studio songs made to fit. Unfortunately, for “Lucky,” the fitting seemed a bit too snug for “Lucky,” especially in light of recent events. In looking back at the past, signs certainly point to the future.

Do you remember where you were when you first heard Britney Spears’ debut single “Baby One More Time”? You might have heard it on the radio. Or you watched the music video for the ground-breaking single on TRL before MTV became a haven for reality shows. It is where I watched the music video for “Toxic” around a million times.

A lot has changed since then, and Britney Spears is one of the few artists to survive the ever-evolving millennium. For one, you probably do not listen to the radio often. So, enjoy the ability to stream Britney Spears’ music. It is far more convenient than a cassette tape. I would know. “Baby One More Time” was the first album I ever got, and it required a Walkman.

Without further ado, it is time to dive deeply into the best of Britney Spears. You can listen to the playlist on Spotify or on Amazon Prime Music. After that, it is up to you. Thankfully, all the songs listed in the following playlist are available to listen to via a Prime account and not on Amazon Unlimited. To the icon behind the music -- thank you, Britney Spears.