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MUSIC HISTORY 101: The Top 50 Tracks of Britney Spears

A lot of things have been said about Ms. Britney Jean Spears throughout the duration of her nearly 25 years as a recording artist and the world continues to have a lot to say about her, especially in the last two years or so. Rarely, though, is the focus on the music itself and she has given us a lot of it, to say the least. It’s a shame, really because for a lot of us, it’s always been the music first, beyond everything else about her. In this update of Music History 101, I want to highlight what I think are 50 of her best tracks throughout her career.

Before I begin, I want to say that I am by no means a Britney scholar. I am a fan, not quite a stan. I am not 100% fluent in her discography, so if I’ve missed some hidden gem, just let me know, seriously! I want to clarify is that these are not the only songs I like by Britney. It took a lot to not include a bunch of songs and get it down to just 50 songs. If a song seems like it is missing, it doesn’t mean I don’t like it and just because a song is ranked lower doesn’t mean I don’t like it. If it made the list, I obviously really like the song.

I will clarify that all of this is meant in good fun and as a way to start a conversation. These are only my opinions and they will probably change a million times in my life. So, with that said..

#50– Ooh Ooh Baby

So, I’m going to start out with a track that shows where Britney was going to go with her sound for years to come really well. I love the guitar part in this song and the melody that she seems to slur through. It’s a subdued bop from Britney but honestly, I don’t listen to this song that often.

#49– Til The World Ends

Second on my list is the club banger anthem of the ages. I think this is a good song but mostly it just sounds too much like Kesha for me. Which isn’t awful, I liked Kesha at the time. I just can’t unhear her in this track. And if I’m supposed to be honest, I wasn’t a huge fan of this whole era because it seemed a little too contrived in comparison to the last two “post-conservatorship” albums. Maybe I’m reading it wrong but to me, this whole thing was too polished and too clean. Not as bad as some tracks on Britney Jean but heading in that direction. I like edgy Britney; this is too safe for me. I didn’t like 'Hold It Against Me' at all.. So if you’re holding your breath for that one, you can breathe now. it’s not gonna be on here.

#48– Get Naked (I Got A Plan)

To me, this is an absolutely brilliant track and one of the standout dance tracks on an absolutely standout dance record. It’s super fun to listen to, it just resonates with any kind of pop loving instincts that I have. It is quintessential Britney but it’s at this placement just because life isn’t fair. Unfortunately.

#47– Shadow

I will say (and I’ll probably get into in a more detailed manner later) that I’m not familiar completely with this album but I know if I had listened to this when it came out, I would have absolutely loved this one at age 12 or so. It’s ballad-y but still has a pop rock edge to it that honestly performs better than any of what her contemporaries were capable of at that time.. Besides maybe Avril Lavigne, whom this track reminds me a lot of. They should’ve collabed, ugh.

#46– (You Drive Me) Crazy

Here’s a possible hot take.. I like this song because it’s fun to sing and it makes me very nostalgic. This is one song of hers my mom would play.. all be it the Stop Remix, which I don’t like one bit… But yeah, this song is very outdated and too much for my 2021, adult ears. When I mindlessly listen to this song, it’s fine. I’m not bothered at all. But when I have to stop and think about it.. I’m cringing a little.

#45– I Wanna Go

Going back to Femme Fatale singles, this is the one I really liked the most. It’s a complete ear worm. It can get stuck in my head even if I haven’t listened to it in weeks, months.. it’s probably stuck in my head right now. I remember this song being one of the first songs I listened to on Spotify on the early days of the service. But I rarely revisit this one, probably because I don’t have to for reasons aforementioned, and that’s why it sits here.

#44– I Run Away

I didn’t grow up with this song in my life due to it being a bonus track on certain issues of this album, but I have really begun to appreciate it in my adult years. The lyrics are some of the best on that album and the songs itself is very beautiful. But.. does this song show up in my playlist rotation? No. Thus, this placement.

#43– And Then We Kiss

This lush, pretty techno remix falls at #43, majorly owing to the fact that it’s a newer find for me as I’ve dug through her deep discography. Even though, to Real Heads, this isn’t that deep but I’m a baby Real Head... so... It’s dreamy, the chorus is very persuasive in its ability to please the desired aesthetic goal. It’s impressive, I believe, for a track like this. And I don’t usually like remixes at all, so the fact that I like this says enough!

#42– Radar

My first Blackout single on this list is Radar at #42. This is one that I played a lot back in the day. It’s hella catchy, but even back when it was released, it seemed like a song made to sell her Kohl’s or Candies or whatever line... but the song itself is still an amazing bop, it was constantly on the MTV video rotation back when I used to be able to wake up early enough to watch music videos on there, if anyone else remembers that long ago...

#41– Lonely

This song is a complete underrated banger! This is another one that’s in my head a lot. When I actually listen to this track, I feel iffy about it at first every time. Then it sucks me in every time. It can be cheesy with the wannabe rock parts of the song that kind of just sound like a caricature of rock music but that pre-chorus is still so good anyway... the little refrain slow down bit... oof. That’s why this song isn’t listed higher, sadly.

#40– Why Should I Be Sad

Bouncy banger Why Should I Be Sad comes in at #39. I love the message of this song, it’s easy to wallow and Britney had every reason to do so on this album. The Neptunes iconic production shows the growth of both Pharrell and Britney at this time. I spent a lot of time with this track in high school and yeah, to me this is definitely one of her most definitive tracks. It’s not listed higher solely due to the fact that it sounds a little like a 'Sweet Escape' Gwen Stefani left over but the fact that Britney co-wrote it.. I hate myself for not having it higher so you don’t have to!

#39– I Will Be There

I do love the sentiment of this song, being very loyal to someone and dependable to loved ones are qualities I find very important in my life. (Britney’s impact?) but what I love most is the way song is sung. It’s fun to sing, it sounds beautiful. It shows off the best qualities of her vocals at this age and really hones in her talent.. If you ever watch her early showcase shows from 1997, you’ll see why people love this song so much. It’s an essential track and I mean that.

#38– Work Bitch

Here’s a classic satire on the capitalism system .. a true song for the working class.. a song of rebellion... In all truthfulness, this song has been my mental amp up song when I have those days I don’t wanna go to work even though I don’t want any of the stuff she lists in the song.. it’s more like, do you want to eat? You better work bitch.. but it works, regardless. I would recommend this method. Also, important side note: I’m in love with Britney’s fake British accent.

#37– One Kiss From You

Our first entry from Oops! lands at #37. I will disclaim here that I am not romantic, I do not participate in that particular lifestyle, but this song very easily makes me understand why everyone was so crazy about it in their teenage years. Seeing a future in someone when it’s hard to see a future.. it’s explained very thoroughly here. Also, it’s a catchy and well written song.

#36– Soda Pop

Moving down the list, we have have Soda Pop from the debut album at #36, which makes little Stevie (me) very sad because this happens to be the first Britney song I ever heard. It was featured on some Sabrina the Teenaged Witch (remember that show? lol) soundtrack CD that my mom bought me, because like most six year olds, I was a huge fan of the show. I just remember playing that song on repeat until my mom literally begged me to stop. Then she wouldn’t buy her album for me.. So I got my unsuspecting grandmother to get it for me. And that was it! My addiction had begun. It all started with this song but now, as the years have passed, it’s just one of those songs that doesn’t say anything. I have no idea what most of the words are to this day but I’m thinking of just fixing that problem and learning them. I can’t live like this anymore.. but the song does sound really good, so it makes the list.

#35– Where Are You Now

The next track is a sappy ballad and may be written off as cheesy by some but I just have a personal relationship with this song due to it being on repeat for an entire week or more or my life when I was like 12. I suppose it just spoke to the melodrama in my soul at that time of my life. This is another fun belter to sing in the shower. If you haven’t tried it, please do.

#34– If U Seek Amy

This next song made a big splash when it came out and I remember it clearly.. like it was yesterday. And I adore this track, it’s so funny and tongue-in-cheek. I feel like it’s extremely catchy and effective, and yeah, controversial in a sleek and clever way. My high school was a little shook by this song. And “3”, which sadly doesn’t make it onto this list. But that’s okay because we have Amy. Also, “ha ha he he ha ha ho” is absolutely genius and a major part of my every day vernacular.

#33– Me Against The Music ft. Madonna

And now we’re really getting to the part of this countdown where things get a little “crazy” (haha) but here is another one I’m reluctant to share my opinion on. I wanna state now, I listen to this song.. I quote this song.. I like this song but I find it kind of ridiculous at the same time. Mostly, I find this song amusing and funny. I absolutely hated this song back when it came out. I was already an emo teen by this point and yeah, this was anti-Everything I Liked. I even liked Brit and Madonna growing up but this turned me off from this whole era in both of their careers. It’s only this high now because I can have fun with it in my adult years and I’m not a stuck up emo brat anymore. Plus, that song by JUSTICE is amazing.

#32– I’m Not A Girl, Not Yet A Woman

My inner child is so mad at me right now for ranking this song so low. I mean, this is a great song with a great message. Its completely on point regarding the feeling of being 18-20 years old, shit maybe even 23. I love singing this song and I love the lyrics.. I do love this song but we’re getting to that point in the list where hard decisions have to be made so.. I said what I said! Moving on.

#31– Touch Of My Hand

This next song is a doozy. I heard about this next track through word of mouth on the internet chat rooms I used to live in during middle school. My internet buddies went crazy over this song when 'In The Zone' dropped and they were pretty misogynistic about it so I just didn’t want to touch this song with a ten foot pole because I, with my adolescent mind, internalized the sexism that was being directed towards her around this time. Also, I wasn’t sure I was comfortable with the subject matter due to.. I was just too young for it! But when I finally got brave enough to listen to this song, which was last year and well into my twenties, I loved it. Honestly, I just wasn’t ready for this song at 12 but it definitely is one of the most impressive songs on this album and maybe one of her most impressive songs in general. It’s just not higher on my list because I’m not that in touch (pun) with it. Yet.

#30– Circus

Oof, this song is so iconic. I recall when it dropped and being like, oh shit. Britney is HERE. And realizing Blackout wasn’t a fluke.. they played the music video for this constantly, which is fine because she is so hot in it.. also, the perfume.. I’ve been trying to get my hands on it for over ten years and it is so hard for me to find. It’s the best smelling thing I’ve ever spritz on my body in my life. So If you know a place where I can get my hands on it for a reasonable price, let me know, thaaaanks.

#29– E-Mail My Heart

We’ve made it through the first 30, and things get a little more difficult from here on out. So, here’s a track that is quite polarizing in her discography. I fully understand the criticism this song gets because it borders on absurdly silly, if not going full blown .. if it were more intentionally silly, maybe it would be better received but honestly, haven’t we all waited for a response to some heartfelt text ..? I liked this track a lot but I loved it after hearing it on vinyl. It just hits different. It just does. This song is awesome, take your arguments elsewhere.

#28– That’s Where You Take Me

That’s Where You Take Me is, to me, just an extremely cute and fluffy song that makes me happy as hell. It’s a perfectly confected sugary, bubble gum pop love song. Honestly, inject this song right into my veins. As to why it isn’t ranked higher.. that’s because her discography is that good, next.

#27– Mood Ring (By Demand)

I have probably her newest solo release (unless I’m stupid and I missed something) at #27, Mood Ring, released in summer 2020.. definitely a highlight of that shitty year. What’s the point of the By Demand part of the title? I can assure you , no one calls this song By Demand when they forget the title. Is it because it was released by demand? I don’t know.. But, yeah, I rotated this song last year very heavily. Why didn’t this make it onto the album? That’s just silly to me.. If you haven’t checked this song out, do yourself a favor and listen to it.

#26– When Your Eyes Say It

I used to not like this song at all and that opinion solely came down to the vocal effects in the verses. I love the “orchestral” arrangement on this song. This is another romantic ballad from Ms. Spears, which as I said, I’m not romantic but I enjoy the idea that your eyes can convey emotions better than your words. In my humblest opinion, this is true in all relationships but really this song is at this placement because it sounds pretty and I love it.

#25– Boys

We’ve made it to the second half of this list. If you’re still here, thank you. It only gets better from here. Boys, the original album mix, makes it to the #25 spot. I loved, loved, loved this song so much when I was little. I didn’t relate to it a damn bit and I still don’t. But it goes off. The lyrics are like.. lowkey so, so good. A Pharrell classic, for sure. The bridge has that classic, lush sound that Britney did so well during this era. Her vocals are chefs kiss.

#24– Don’t Go Knockin’ On My Door

I don’t even know exactly why I love this next track but I do. I listen to it literally all the time. It just satisfies me in an unexplainable way. It definitely shows her maturity from Baby to Oops, but it’s still youthful enough to be fun. It gives that album an essential flavor that is just necessary to who she is an artist. I don’t know what popular opinion is on this track, but I will defend this song til I die. Let me know if you feel the same.

#23– Blur

Listening to Blur in our post-#MeToo culture is a little jarring to say the least. I’m not sure if it’s content warning worthy but I promise to be as vague as possible if you’re not comfortable with sensitive topics. It just definitely goes to show how far we’ve come in a little over 10 years regarding these kind of subjects. Now, with what I know as an adult, it makes this track a lot darker and more sad, honestly. But, this always been a favorite of mine from Circus because it shows variety in what she is willing to touch on as an artist. And it’s not victim blaming, it’s neutral. It may be accurate to the real experience. It’s interesting, to say the least.

#22– Out From Under

Out From Under is another one from this era that’s very interesting in its subject matter, whilst not being controversial. It’s quietly triumphant, that moment when you’re still in the depth of devastation but knowing you will make it through by knowing your self-worth. It’s definitely empowering, it runs in the same vein as tracks like I Run Away but it is written a lot better. It shows her and the talent that supports her were definitely blossoming.

#21– Sometimes

This is almost as bubble gum as it gets and it’s fantastic. It ranks here because of how embedded into my DNA it is after all of these years. I probably learned how to enjoy singing while singing this song, not that I’m any good at it but I enjoyed it a lot when I was a kid and this was a definite go-to for me. Besides that, it’s very well written and the message is positive. She’s setting boundaries and that’s good for girls to hear. It’s funny how she was “bad for youth” yet had songs like these.. That’s a topic for another article.

#20– Bombastic Love

Our top 20 finishes out with a deep cut from Britney. Yeah, I don’t know why I love this song so much because I know it’s a little over-the-top and all that, but it’s just one of those Britney songs I carried with me regardless of what musical landscape I was exploring throughout my life. I think I just like the idea of bombastic love, for other people not myself, and I think it’s an interesting adjective to use in a pop song. It’s that simple. I like the song.

#19– Unusual You

What a great song, the vocal effects really work here. Her vocal works really well on this song in general. Again, this is a dreamy Britney track, which I don’t even think I would mind in a remixed form.. it just works as a song, and it could’ve been produced in a number of ways and I still would probably like this song.. I wonder if that exists.. anyway, I love this song!

#18– Break The Ice

But not as much as I love this next song.. The opening line is iconic, they played this song on MTV constantly and yeah, what a vibe that was. It’s just the perfect song for that period of time and I can’t skip this track when it comes on even if I try. I do think I may have overplayed it back in the day but I’ll forgive myself. I couldn’t help it. It’s edgy Britney in her finest form.

#17– Man On The Moon

Unfortunately, this is the only song from the original release of Glory that will be on this list, which just shows how good her discography is because I barely scratched the surface.. but, I love, love Man On The Moon with my whole ass heart. It reminds me of like Melies films, which may seem like a stretch but .. it’s called Man On The Moon and she speaks French.. And bless her, her French is so bad.. but it just makes me like the track even more. The vocal effects are used very effectively here, the track is just a great ear candy piece of deliciousness. It’s a fantastical bop and I will defend it with my life.

#16– Breathe On Me

Here’s another song I can’t relate to. The production on this track is literally impeccable and I fully believe that she is capable of achieving a level of arousal that only requires respiration from her partner due to her vocal delivery here. I’m a bit of a square so I find this song embarrassing to listen to, especially with other people or just one person, but it still is such a good song and it’s very, comment-dit-on.. Vibey.

#15– Thinkin’ About You

Not to be confused with Ariana Grande’s classic Thinking ‘Bout You, Thinkin’ About You falls at #15. I can’t believe we’ve made it this far.. but, I love this song. Her vocals are so unique here and so Early Britney, and the song is so cute. It’s bubbly and groovy, it sounds like summertime. It’s a great riding or driving in the car when it’s hot outside song. Definitely a definitive bop and perhaps, super underrated. I don’t really know the discourse on this album. Someone fill me in..

#14– Gimme More

This next song is a classic game changer. I remember being so confused when this dropped, which in hindsight, means it was revolutionary. I initially felt like I didn’t want to like it but I couldn’t stop listening to it.. It’s an absolute classic at this point. I don’t think anyone knew when this dropped what an impact it would have but everything shifted after this one. It’s truly iconic, I’m just sorry her discography is so good that this one only makes it to this ranking on my list. I don’t think we still know how good this song is over a decade later.

#13– Toxic

I could say everything I just said about Gimme More about this song as well. This was an earth-rattling hit that was completely unavoidable in my 6th grade year of school. I heard this at least 3 times a day at some long point in my life. I don’t really truly trust people who don’t like this song. If any other artist had released this song, they wouldn’t have been able to handle the weight of it in their discography. But it’s so well supported in Britney’s that it’s almost like.. a blip in the grand scheme and hard to fathom how huge it was. It’s so different from what else was coming out at this time.. it blew my little baby mind and over saturated our airwaves.. it’s truly iconic.

#12– Lucky

I remember being little and having a sing-a-long in my class with the other girls to this one.. how wholesome is that? And wearing my Britney shirt to school everyday.. Ow, my fefes. Anyway, I love this song obviously. I’m getting into all-time favorites category but the story is intriguing, the announcing in the bridge.. so 90s but it’s like one of my babies. I will forever love this song. I will forever sing this song at the top of my lungs whenever I want to, word for word, note for note.. This song should be as regarded as fucking.. Satisfaction or something.

#11– Overprotected

And I will forever love this next song.. Overprotected from Britney rounds out our top 40 and lands at #11. I know no one knows me but this used to be my Twitter username for ages. I miss that.. anywho, again, I’m talking about the original album mix because I don’t like remixes. Why did this song have so many versions and videos? We’re they that desperate to make it a hit? Kinda funny.. but, regardless, it’s a definitive hit in my heart and that’s all that matters. The subject matter is pretty relatable for young people. Everyone just wants to their from their mistakes on their own and you have to let them do it. It’s almost sad to listen to know, considering how her life has turned out. A lot of her discography makes the conservatorship really depressing to think about, honestly..

#10– Stronger

I’ve made it to the top 10.. and that’s where Stronger takes it’s place. This is one of those songs that embarrass me in front of people because I can’t control myself. I just.. the clap gets me every time. It’s just irresistible. The message, the vocal, the instrumentation, the production.. absolute banger. It’s bitchy enough, it’s petty enough, it’s verbose enough.. the breakdown where it likes fades out and comes back.. it feeds my soul. I need this song to muddle through existence.

#9– I’m a Slave 4 U

This is the only song that may have worried my mother growing up. As a pre-pubescent child, this song was scandalous .. and intriguing. But mostly, it was a bop. It still is. It’s one of her most impressive lead singles, for sure. I mean, I know it’s not the most profound song ever and it’s title can be a little jarring, but it’s just goes off, simply put. The video is immaculate and beautiful. It really shows why she was such a big deal, when people will continue to look back at her career for years to come. No other pop girlies in recent memory can pull off what she does in this song and the promotion for it. It was a moment and she owned it.

#8– Mmm Papi

This is an underrated bop. Again, with a little bit of an uncomfy title and subject, but ugh, I love this song so much. It’s just fun. The guitar part, the keyboard part, the vocal delivery.. I listened to this so much when I was in high school, I think it was in my top 5 played tracks on iTunes back in the day, which means I listened to it at least 200 times in one year. At least. I would defend this song to my last breath, hopefully I don’t have to..!

#7– Oops!… I Did It Again

Okay. What can I say about this pick? From the first NOTE.. it goes off. It’s unmatchable! It’s iconic! It’s forever! It’s everything! It’s like God in a song.. The bitch did what she had to do. I remember being like six or seven years-old and just losing my little mind over this. The Titanic reference.. The choreography.. it’s like it was made for me. I learned the entire choreography just from watching her performance on All That.. what an era.. it’s power is unwavering, it will always be one of my favorite songs of all time. Most of this list probably will be but I’ll for sure be blasting this at the nursing home.

#6– From The Bottom of My Broken Heart

This one is quite different from my last pick, but powerful none the less. From The Bottom of My Broken Heart is definitely one of her cheesier ones but it’s so good. This is one I listen to a lot in the car and sing my heart out to. Or anywhere I hear it. I mean, it’s obviously the twin to Born To Make You Happy but I just don’t know if it’s my favorite twin and that hurts my feelings to say but.. it’s made it very high up the ranking.. so, that counts for something.

#5– Anticipating

I can’t believe I’ve made it to the top 5 already, so at #5, I have the epitome of bubble gum Britney pop, Anticipating from Britney. This should’ve been a more promoted single but like, I understand.. anyway, if you couldn’t tell, I love sugary, sugary pop music and this satisfies that pop sweet tooth, to me, better than any other song in her discography. It’s good in the car, it’s good at the beach, in the shower.. it’s good anywhere. I put it on like, 80% of my playlists, honestly. It’s just, it’s neutralizes the palate..

#4– Don’t Let Me Be The Last To Know

Don’t Let Me Be The Last To Know is my #4 choice, it’s perfect to sing along to. I don’t have a high register, I’m somewhere around Britney’s range (nowhere near her talent but) this one is just easy on the wind pipes. Also, I love Shania Twain a lot, and this is very much like the two of their sounds mushed into one so it’s just.. ideal, to say the least. What a power ballad. Ugh. And learning that it was her favorite from the album too? I feel validated.

#3– Born To Make You Happy

Here’s the other twin at #3, Born To Make You Happy. This choice comes solely down to melody and lyrics. It’s fun to sing, I have always loved this song. This song was born to make me happy, (ha ha he he ha ha ho). But really, I have a lot of special, happy and simple memories attached to this song. It’s another tune that is constantly being sung or played in my home. It’s an overly emotional ballad for the young at heart, isn’t it? (I just have a lot of feelings)

#2– Everytime

Oh, god.. This song takes the absolute cake when it comes to emotional ballads.. it’s the pinnacle.. you know what I’m talking about, it should’ve been the final track on In The Zone.. but that’s a topic for another day… I don’t listen to this song as much as some of the others because it just makes me too sad. I have cried to this song for .. almost twenty years. I have so many memories of listening to the top 40 radio and being like 12, this song coming on in the middle of the night and just crying my little tweenie eyes out. It’s just, that deep sorrow and regret.. it’s so palpable. And the track itself is so, so beautiful. This is a perfect song, no one can change my mind.

#1– …Baby One More Time

I don’t know what to say about this song that hasn’t been said a million times. Rolling Stone magazine recently named this the best debut single of all time, and let me say.. they’re not wrong. This wasn’t my introduction to Britney but it still impacted me the same. I remember hearing this for the first time in my Grandmas car.. it blew my little mind. I knew, even at age 5, that I was hearing something special. And I still feel the same way each time I hear it. I feel a little bad for having it at #1, because it’s such an obvious choice but Jesus, this song just goes absolutely off. It changed the music industry and it hasn’t lost any of that power throughout time. I will blast this song so loud in the nursing home, in the grave, in the cosmos… I honestly don’t even know what kind of person I would be without this song. I reluctantly stand by my decision because I really cannot choose anything else to be #1. If this isn’t your number one pick, you’re probably lying to yourself. I said what I said.

You can find the full Top 50 in playlist form below, curated by Stevie Kristian (@ietmerollit).

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