Each Music Monday will be formatted as followed: an overview/ my opinion on their said career, followed by the ranking of their top 5 songs. No artist is without flaws, their worst three songs will also be judged and ripped to shreds.

As a reminder, this is not going to be a series where I list no-name songs off an artist’s shitty second album that’ll you’ll hear occasionally in an urban coffee shop. We only grade hits here. I’m not looking for songs that have the best underlying message. I’m not looking for songs that represent the artist’s struggle and triumph over something shitty that happened to them. I don’t care about any of that. We are only ranking the cream of the crop, the pinnacle of an artist’s success. Before you ask, I will not be ranking The Beatles’ songs, as I do not want to tarnish my blog with overrated garbage. If you have a problem with that, or my rankings, and want to make your criticisms known, you can email all of your concerns to VinnieWontCheckThis@gmail.com. Prior versions of this series can be found here.

Anyone who knows me knows that I love Britney Spears with all my heart. She is without a doubt, my favorite artist. To me, she is the real Queen B and it is not even remotely close. There are certain artists I hold off on doing a Music Monday post on because I am saving them for special occasions. Due to unforeseeable circumstances preventing me from doing Music Monday’s for two of the past three weeks I figured I owe it myself to do an artist I enjoy talking about. I won’t get into much detail on that, however, you can call it a Stroke of bad luck. Regardless, we are back; so with that, let’s get started.

Britney Jean Spears was born on December 2, 1981 in McComb, Mississippi. At age three, she started attending dance lessons in her hometown of Kentwood, Louisiana, and was selected to perform as a solo artist at the annual recital. Spears made her local stage debut at age five, singing “What Child Is This?” at her kindergarten graduation. During her childhood, she also had gymnastics and voice lessons, and won many state-level competitions and children’s talent shows. At age eight, Spears and her mother Lynne traveled to Atlanta, Georgia to audition for the 1990s revival of The Mickey Mouse Club. They rejected her for the show because she was too young, but they introduced her to a talent agent in New York. The agency was impressed with Spears’ singing and suggested enrolling her at the Professional Performing Arts School; shortly after, the family moved to a sublet apartment in New York, eventually getting cast in The Mickey Mouse Club three years later, in 1991. (You probably know this already, but if you live under a rock, the other people cast in Mickey Mouse Club were Christina Aguilera, Justin Timberlake, Ryan Gosling, and Keri Russell. Just an unbelievable amount of talent on one show). In 1997, at the age of 16, a record label approached her to join and head a Girl Group, but her representatives knew she was too much of a talent to be pigeonholed into a group, and was instead flown to Sweden to begin recording her debut album. Her debut studio album, …Baby One More Time, was released on January 12, 1999, and on this day, Britney Spears became Miss American Dream, at the age of 17. It debuted at number one on the U.S. Billboard 200 and was certified two times Diamond. It remains the best-selling album by a teenager, as well as the best debut album time, selling over 25 million copies. The title track was released as her first single, hitting number one on the charts and becoming one of the best selling songs of all time. The other three singles off the album went top 10 (You Drive Me Crazy) and had two top 20 hits as well (Sometimes, From the Bottom of My Broken Heart). Due to the success of this album, Britney was credited with leading the revival of teen pop. How does a teenager follow up the most successful debut album of all time? The expectations were high, especially for an 18 year old, but boy did she deliver. Oops!… I Did It Again, her second studio album, was released in May 2000. The album was a commercial success, selling 20 million copies. The singles all charted in the top 20, with one song in the top 10 (Oops! I Did it Again) (which is absolutely crazy how this song only hit number 9 on the charts. It’s actually absurd). The other two singles went number 11, (Stronger) and 20 (Lucky), respectfully. (Which again, feels very low. These songs were everywhere). Her third album Britney came a month before her 20th birthday and surprisingly only had one song chart in the top 20 (I’m A Slave 4 U). Many viewed Britney as a transition album for her and her career- as she Wasn’t a Girl and Not Yet a Woman. However, album number four, In the Zone, is where she has finally completed that journey and turned into Britney, the Adult Woman. In the Zone was released in 2003 and marks a musical departure for Britney. Instead of traditional pop, the album is darker and more dance-oriented. It spawned a top 10 hit, and arguably her biggest one (Toxic, which has me noticing a pattern here, this song ALSO peaked number 9 on the chart, it makes no sense to me) and also had a top 20 hit/apology to Justin Timberlake for ruining their relationship (Everytime). This is the point in Britney Spears’ career where she began to lose her way a bit. She married Kevin Federline after dating for 3 months, meanwhile she announced that she was releasing a greatest hits album so she can take a hiatus from her career to start a family. (How many artists can you say are capable of having a Greatest Hits Album at the age of 22, just an unbelievable flex and one of the many reasons why Britney is the GOAT). The greatest hits album had one ‘new’ song, a cover of Bobby Brown’s 1988 jam My Prerogative, which didn’t chart because at the time cover songs weren’t allowed on the Billboard Hot 100. In my opinion, this was where her struggles began to creep out little by little. I will not be talking about these struggles however, because, just like I didn’t talk about Chris Brown’s issues when I did his Music Monday– we only grade hits here. (However, if you want a refresher on the three year ordeal that Britney had, you can read about it here). She made her return to music in 2007 with Blackout. Her big return spawned a top five (Gimme More) and a top 10 hit (Piece of Me). Blackout received widespread acclaim, with some citing its influence on pop music years later and it also ranked on many end-of-decade lists. In 2012, the album was added to the library and archives of the Rock and Roll Hall of Fame. This album received way more acclaim than I thought it would- don’t get me wrong, it’s a really really good album, I just didn’t expect it get inducted into any sort of Hall of Fame. But regardless, Britney was back! Her comeback was followed by her sixth album, Circus, which was released on her 27th birthday. The album was lighter than Blackout and no that’s not a pun, the songs on this album were less edgy than it’s predecessor. It had songs go number one (Womanizer)– which was her second number one hit; which is still absurd to think about- three (Circus) and nineteen (If U Seek Amy). 11 months after she released Circus, she released another Greatest Hits Album, which had another number one hit (3). (Imagine having two greatest hits albums before turning 28, just absolutely crazy to fathom, Britney is the queen for a reason). In March 2011, Spears released her seventh studio album Femme Fatale. With this album debuting number one on the chart, Britney tied Mariah Carey and Janet Jackson for the most number one albums by a woman. After being screwed by the Billboard charts early in her career, Britney was finally getting her respect, with all three singles reaching the top-10. The singles chatted at number one (Hold It Against Me), number three (Till The World Ends), and number seven (I Wanna Go). A couple months later she appeared on the remix of Rihanna’s hit S&M, which pushed that song to the top spot of the chart- her fifth number one and her fourth in three years. She took another little break from music to get paid $15 million to be a judge on The X Factor, becoming the highest paid judge in any singing competition ever. I don’t blame her, chase that bag in anyway you can sis. In late 2012, she was featured on will.i.am’s top three hit Scream & Shout, giving Miss American Dream the best selling song of 2012. Even in a year she didn’t release any music she made $58 million. Incredible. Britney Jean, her eighth album was released in 2013, on her 32nd birthday. I say this as the most bias-unbiased Britney Spears fan- this was her first bad album, it took half of her life, or 16 years of making music for it to happen, but it happened. Should have just called it Britney James because, much like LeBron, her consistency for all these years despite all the controversy and hate over the past 16 years is something we will never see again. Despite the album being below average it had a top fifteen song (Work Bitch). Her ninth album, Glory, was released in 2016, and can be called her “Michael Jordan on the Wizards” album. All is not lost though, it still managed another top 20 hit despite being a stinker (Make Me). Since then, she has been entangled in a legal battle over the conservatorship that has been in place since her meltdown in 2007, which has threatened her career going forward. I promise not to go into detail about what it means, but for the curious, you can learn all about that here. If this marks the end for Britney all we can do is be grateful for everything she’s given us the past 21 years. So with that let’s move to the rankings.

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This is kind of a cop out for me but it makes sense in my head. Since I missed last week’s Music Monday and since only ranking five of Britney’s best songs is impossible for me to do, we are opening this ranking up to her TEN best songs. Also I did some digging on why her songs didn’t chart as high as you would think until later on in her career, as it turns out, back in the early 2000’s when radio plays were the only thing that impacted where your song went on the chart, due to their promiscuous nature, and her unwillingness to sign a touring deal with iHeartRadio, there was a radio ban for all Britney Spears’ songs during her peak. While this does impact a couple of songs that you could put in her top ten, due to her mass collection of hits, I easily managed to get ten. I could have done 20 tbh but that eliminates the point of a list.

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10. Work Bitch– You can make the argument that out of all her songs, this one had the biggest impact on our country. How many artists can say they single handily improved the U.S Economy– the answer is one. GOAT.

9. Womanizer– This song is responsible for the feminist movement that we’ve seen in this past decade. Fun Fact: Susan Anthony added the B to her name for Britney after being inspired by Womanizer to fight for women’s rights. I love U.S History.

8. Circus– This is the least controversial Circus out there. I hate who I become when this song comes on. It’s like I transform into one of those Animorphs. They just don’t make pop classics like this anymore.

7. I’m a Slave 4 U– People who were not alive during 2001 – 2003 will never truly be able to grasp how UNTOUCHABLE Britney Spears was during these years. The quality of the performances…. Artists today could only dream.

6. Stronger- Before Lizzo’s ‘Truth Hurts’ there was this song. I’ll admit that I’ll blast this banger and before the song ends I’ll tell myself , “that wasn’t enough” and start it over from the beginning.

5. Lucky– This is one of the sadder songs when you dive deep into the lyrics and see how much it actually emulates her real life. Sort of depressing but the song slaps. Just a straight power-ballad. This is the musical equivalent of Bojack Horseman the more I think about it.

4. Gimme More– “It’s Britney Bitch” is the most iconic opening line for a song ever and I refuse to believe otherwise. I’m dead serious when I say they are the three most iconic words in the English Language.

3. Toxic- This song means so much to me and I say that with the upmost sincerity. I was nine years old when this song came out, and the music video for this song served as my sexual awakening. So to all the ladies reading this, if you’ve gotten a DM from me that you’ll never answer, thank Britney for that.

2. …Baby One More Time- The song that started it all. The fact that she did this when she was 16 continues to blow my mind. Just think about what YOU were doing at 16. I was ugly and depressed and worried about Pre-calculus and acne and high school bullies. Heck, you can even go deeper with it and just think about every album release, every milestone, every low point, every scandal, everything that Britney went through at her young age, and think about what you were doing and what problems you were going through? The meltdown makes so much sense.

1. Oops… I Did It Again– Britney went from super stardom to legend status when she dropped this classic. ‪I wish I constantly as happy as I am when I hear that beat followed by Britney’s “nnnyeah.” There are few greater moments in pop music than the triumphant reiterated “OOPS I” during the bridge of this thing. It’s probably the greatest pop song of all time, and that’s not an opinion, it’s a fact.

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Britney Spears’ Worst Songs

Lol imagine thinking I’d talk negatively about the Queen of Pop after I wrote over 2,200 words about her career. Not now, not ever. Let someone else rank her worst songs, it won’t be me.

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Your Turn

If you had a blog and were to rank every Britney Spears song that hit top 20 on the charts, what are your top 5?

Title	Year	Peak chart positions	Album
…Baby One More Time	1998	1	…Baby One More Time
(You Drive Me) Crazy	1999	10	…Baby One More Time
Sometimes	1999	20	…Baby One More Time
From the Bottom of My Broken Heart	1999	14	…Baby One More Time
Oops!… I Did It Again	2000	9 (what a joke)	Oops!… I Did It Again
Lucky	2000	20	Oops!… I Did It Again
Stronger	2000	11	Oops!… I Did It Again
I’m a Slave 4 U	2001	20	Britney
Toxic	2004	9 (LMAOOO)	In the Zone
Everytime	2004	15	In the Zone
Gimme More	2007	3	Blackout
Piece of Me	2007	10	Blackout
Womanizer	2008	1	Circus
Circus	2008	3	Circus
If U Seek Amy	2009	19	Circus
3	2009	1	The Singles Collection
Hold It Against Me	2011	1	Femme Fatale
Till the World Ends	2011	3	Femme Fatale
I Wanna Go	2011	7	Femme Fatale
Scream & Shout (with will.i.am)	2012	1	#willpower
Work Bitch	2013	12	Britney Jean
Make Me… (with G-Eazy)	2016	17	Glory