…Hit Me Baby (Fifty) One More Time: The 51 Greatest Britney Spears Tracks Ever

“Personally, I am still reeling from the events of this past weekend.”
“The Super Bowl?”
“No, the Britney documentary.”

The above is how I started every professional Zoom call the week after the New York Times documentary Framing Britney Spears premiered, educating and radicalizing me in the #FreeBritney movement.  The doc, streaming on Hulu, is a blistering deep-dive into the media’s sexist, misogynistic treatment of Britney Spears throughout her record-breaking career. It also tackles the troubling, abusive conservatorship she’s been in for over a decade, overseen by her father.  

While the documentary opened up yet another crucial conversation about the media, our treatment of female celebrities, and the stigma of mental illness, it also was an important reminder of something that has gotten lost in Late Night host punchlines: Britney is a fucking star.  Quite simply put: Britney Spears is one of the most influential, successful, and talented music acts of the last 20 years. 

My relationship to Britney Spears was similar to that of any sexually confused high school senior at the time of the release of “…Baby One More Time.” Lust for Britney and desire to learn her choreo in equal measure. If only I had figured out what that meant, I could’ve saved myself a ton of time and therapy. Her specific impact remains unchallenged. I have other musical memories, sure: I cried when I received a Tiffany t-shirt for my 7^th birthday, and I have distinct memories of sneaking off to watch forbidden True Blue-era Madonna videos on MTV. I auditioned for a talent show with a backing track of Whitney Houston’s “Greatest Love of All,” after which my music teacher gently put her hand on my shoulder and simply said: “No.” In retrospect, I suppose the signs of my bisexuality were everywhere. 

But with Britney, it was different.  I’ll never forget piling into our friend Josh’s beat-up old Ford Bronco, cutting school to go to the mall (!) to buy the cassette single (!!) of “…Baby One More Time” at The Wall (!!!). We listened to it on repeat, even Josh, whose sensibilities ran much straighter and Offspring-y than mine, or any of our gal pals who joined the excursion. Our friend Kristin performing the choreography from the video. We all did our versions of “ooh BayyyBeee BayyBeeee how was I supposed to knaaaaaaw” incessantly. 

Over the years, I made the excuse of taking my younger cousin to see a Britney concert not once, but I believe twice. Britney was never the safe space for me that she was for so many people, but there was certainly something about her I was always drawn to, something that was decidedly queer-adjacent. 

Despite this last and the thousand or so words you’ve already read, I wouldn’t say I’m anywhere near Britney Spears’s number one fan or, dare I say, even a stan. But there is a kinship. Britney Spears and I are the same age, so while she was conquering the world, I was in college. When her life was the subject of rampant speculation, I was getting my career started. When she had her first “comeback,” I was being promoted. Now we’re both full-fledged adults.  One of us is a mother with an incredibly hot boyfriend who remains the biggest pop star in the world. The other is a single, soon-to-be 40-year-old bisexual who recently turned his Britney Spears t-shirt into a crop-top he will never be comfortable wearing in public. Life is funny. 

If you want to listen along, you can do so with this lovingly curated Spotify Playlist. If you’d like a deeper dive into the world of Ms. Spears, please enjoy all 119 of Britney’s singles, and album tracks ranked (devoid of Bonus, non-single guest tracks, and anything having to do with Kevin Federline). It takes a while to get to a stinker.

Without any further ado, let’s get to work bitch. 

#51 “Scream & Shout” – #willpower (2012)*

Technically a cheat because this is supposed to be a Top 50 list, so why the heck is there a number 51? Well, much like Britney, I make the rules here. And even though I don’t love this song, Britney speak-singing the chorus of a will.i.am track in a British accent is essential. When someone asks you to define camp, please have them listen to this. 

#50 “Blur” – Circus (2008)

Britney explored morning-after malaise in previous songs, like “Early Mornin’” from In the Zone written by, of all people, Moby. This one has the real sense of haze and regret of waking up in a state of confusion that is, uhh, quite relatable. 

#49 “Me Against the Music” – In The Zone (2003)

It’s undeniable: Madonna and Britney together was a moment, inching this collaboration been the Pop Icons up several spots on this list. Far from a strike-out, just more of a solid double (this is a weird post to use sports metaphors, right?), but undeniably a cultural touchstone.

#48 “Deep In My Heart” – …Baby One More Time (1999)

This hidden gem! I never let go / cause I love you so / Whoa Oh Oh  / I want you for the rest of my life! Is a chorus you could imagine, say, Barb & Star losing their minds over while trying on culottes at the local Vista Del Mar freakin’ Chico’s. I can’t express enough how much this is my highest form of compliment.

Completely unrelated: I watched Barb and Star Go to Vista Del Mar three times during my 48-hour rental window. 11 months into the pandemic, and I finally feel ALIVE.

#47 “Clumsy” – Glory (2016)

The hand-clapping, the vocal range, the beat drop. Just an absolute blast. 

#46 “Sometimes” – …Baby One More Time (1999)

Britney’s second single – and second hit – maybe a little low on this list for some fans. For me, its place in the pantheon should be more remembered for setting the blueprint for Disney stars-turned-Pop sensations. It’s a pretty short walk from: “Sometimes I run / sometimes I cry /sometimes I’m scared of you” to Hillary Duff singing: “Why not (why not) / Take a crazy chance / Why not (why not) / Do a crazy dance.”

#45 “(I’ve Just Begun) Having My Fun” – Greatest Hits: My Prerogative (2004)

A perfectly fine, funky song bumped up roughly ten spots for its inclusion in the post-airplane walk of shame from Bridesmaids. 

#44 “Don’t Go Knockin’ On My Door” – Oops!… I Did It Again (2000)

A great kiss-off track that successfully treads in some of the Spice Girls territory of the time. 

#43 “Hot as Ice” – Blackout (2007)

Nothing about this song makes sense except that I want to be dancing to it right now. (Spoiler alert: I am.)

#42 “Lace & Leather” – Circus (2008)

Britney’s legacy as a queer touchstone was long assured by the time Circus rolled into town in 2008. So you might imagine that for a large swath of her audience, there is nothing better than a song in which Britney plays dominatrix over a synth electric guitar. I am large; I am swath. 

#41 “Where Are You Now?”  – Oops!… I Did It Again (2000)

Low-key one of the best Britney ballads. The drama. The pleading. The money note! An underrated fav. 

#40-31…