Britney Spears’ 5 Greatest Hits of All Time

It’s hard to believe that we were introduced to Britney Spears 20 years ago. Her debut single, “…Baby One More Time” was released on October 23rd, 1998 and helped propel her into the global superstar that she is today.

Britney was my generation’s Madonna. She was my generation’s Barbra. She was my generation’s Cher. She was everything to me as a gay kid growing up in Long Island and I still have a ton of love for her all this time later.

She had that something that millions of people gravitated towards. When the pop boom was happening in the late 90’s, she was the first female to emerge from it. There were plenty of other women who came after her (Christina Aguilera, Jessica Simpson, Mandy Moore), but Britney stood out from the rest not because she was a stellar vocalist but because she was the total package of being a phenomenal entertainer.

It’s like what RuPaul says on RuPaul’s Drag Race: charisma, uniqueness, nerve and talent. She had all of that and then some and continues to delight audiences to this day with her irresistible hits, fashions, dance moves and the fact that she’s lasted longer than many predicted she would (see: 2007).

Given that the 20th anniversary of “…Baby” is coming up, I thought it would be good to take a trip down memory lane and make a list of what I believe to be her five best singles of all time. I am only including songs of hers that ended up on the Billboard charts, so masterpieces like “Showdown” and “Don’t Go Knocking on My Door” sadly won’t make this list.

Take a look at what I believe are her five greatest singles. Do you agree? Let us know in the comments section.

5. “You Drive Me Crazy (Stop Remix)”

The third single off her diamond selling debut album, “Crazy” was given a fantastic remix that became part of the Melissa Joan Hart movie and soundtrack of the same name. Not only is the beat fantastic, but the video is stellar with some great choreography and Britney looking simply superb throughout it all. It became her second song to hit the top 10 and helped solidify her into a pop princess at the time.

4. “…Baby One More Time”

The one that started it all. It’s widely considered to be one of the best pop songs ever and in many top ten lists of the best tracks from the 90’s. Everything worked with it. The “Oh baby, baby” part, the Catholic schoolgirl theme that everyone was rocking on Halloween in 1999 and so much more.

3. “I’m a Slave 4 U”

Let’s keep it real here: we all wanted Britney’s abs circa 2001 after this dance-filled, sweaty video came out. “Slave” was a big shift from her first two efforts and saw the then 20-year-old become a lot more mature in her sound and appearance. It paid off and then some, as we all still remember the sick choreography and that snake she danced with at the VMA’s later that year.

2. “Toxic”

How in the freaking hell did this song not hit number one here? “Toxic” is Britney’s second signature track, outside of “Baby”, IMHO. It’s her only song to win a Grammy (Best Dance Recording) and is one that this writer will never get tired of listening to. Plus, she gets to ride on a motorcycle with Tyson Beckford in the video. Woof.

1. “Gimme More”

It’s hard to believe that Britney’s best effort was when she was at her lowest point. Blackout is an amazing album, and “Gimme More” was a fantastic lead single that remains her best to this day. It was unapologetically and overtly sexy, something that Britney teased beforehand but never really sank her teeth into. This to me was her version of what Madonna did with “Justify My Love”, and this single and album would’ve been so much bigger had the media not destroyed her all that time ago.

This post was created by one of our Contributing Writers and does not reflect the opinion of Instinct Magazine or the other Contributing Writers when it comes to this subject.

2 thoughts on “Britney Spears’ 5 Greatest Hits of All Time”

  1. Urgh. Gimme more and Slave

    Urgh. Gimme more and Slave should be out of this list. Oops, Overprotected, Sometimes, Till the world ends, are much greater hits.


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