In celebration of my 30th birthday, and the 20th anniversary of ‘Oops!…I Did It Again’, the song that made me and so many other young gay guys fall in love with pop music, here is my personal ranking of every Britney Spears song, including B-Sides and features, ranked according to my taste aka correctly. I have dedicated an obscene amount of my life on Earth listening to Britney Spears songs and knowing her life and career inside out. (Pun alert!) I would go as far as to say that I would not have become very interested in pop music if it were not for Britney Spears, one of the only worthwhile celebrities, and someone who has managed to remain a real human being despite the insanities of the pop music machine.
Here and there on the list I will make comments and link to videos.
It’s kind of unfair to the other pop divas of Britney Spears’s generation how much catchier her songs are than everyone else’s. She’s got dozens of songs with fantastic hooks, and after her first four albums redefined teen pop for a generation, her career had a second phase in which she embraced dance-pop and electro-pop, during which her music actually got even better. Nine albums in, song for song, her hit-to-miss ratio remains very strong. The rollercoaster ride of being a fan seems to be all but over, but it’s been quite a ride.
Her albums, ranked: Blackout (A), Femme Fatale (A-), In the Zone (A-), Britney (B+), Circus (B+), Glory (B+), Oops!…I Did It Again (B+), Britney Jean (B-), and …Baby One More Time (C+).
Her songs, ranked:
- Gimme More
It’s Britney, bitch! This song’s dark, slightly sinister atmosphere, anxious synths and chants, and relatively untreated vocals create a sense of claustrophobia and urgency. It’s so catchy. - Get Naked (I Got a Plan)
This song is manic. The production on this track is dizzying and intoxicating, and Britney has never sounded so desperately erotic. This song makes me laugh when I listen to it from the sheer gonzo zaniness of it, even as it makes me want to dance. - I Wanna Go
Probably her single catchiest song. Instantly addictive. - Toxic
It’s emerging as a modern pop classic for a reason. - Hold It Against Me
Criminally underrated among her lead singles. - Til It’s Gone
‘I Wanna Go’ re-imagined as a heartbreak song. - Bombastic Love
Her best song with Max Martin. Jive Records wanted this as the third single, but Britney balked, since it was such a typical Max Martin bubblegum song. Yeah, but it was really good; much better than ‘Overprotected.’ The pseudo-operatic bridge is amazing camp, and the little flourishes of counterpoint in the final chorus are vintage Britney and Max.
- Love Me Down
Easily the catchiest song on 2016’s Glory. - Trouble for Me
A late-album stunner from an album that otherwise starts to drag in its second half. - Shattered Glass
It feels incomplete, but what’s there is a shimmering, crystalline sadness pervasive in Britney’s discography - Hold On Tight
This song is actually Britney’s best ballad; how this got resigned to a B-Side on her worst later-career record is beyond me. - Breathe On Me
One of the sexiest songs Britney ever recorded is an ode to monogamous sensuality — surprise! - Till the World Ends
Her biggest hit of the 2010s and a sort of time capsule of 2011 in pop music, especially the remix with Nicki Minaj and Kesha - Everytime
Who could have pulled off this song like Britney, with her fragile, vulnerable tone? - Circus
The second of a one-two knockout punch of comeback singles - Man On the Moon
The epitome of bittersweetness - The Hook-Up
This should have been the fifth single on In the Zone, following ‘Breathe On Me’ - Womanizer
A damn good comeback single - Can’t Make You Love Me
The best song on Oops!…I Did It Again is buried near the end - Cinderella
Like ‘Bombastic Love’, I’m-not-a-little-girl-anymore Britney was embarrassed by this song, but two decades later it’s obviously a bubblegum highlight. - Amnesia
How the hell did this song get relegated to foreign-bonus-track status? - Oops!…I Did It Again
- Lonely
- Stronger
- …Baby One More Time
You know a pop singer’s discography is incredible when her singnature song isn’t even among her twenty best! - Lucky
- Clumsy
- Phonography
Another killer b-side; Circus had a very confused track list - Freakshow
- Inside Out
- Let Me Be
- Piece of Me
- Alien
A bittersweet little piece produced by William Orbit, the mind behind much of Madonna’s Ray of Light - 3
The lyrics to this song are hilarious, and the video is very underrated - Heaven On Earth
- I’m a Slave 4 U
- What U See (Is What U Get)
- Born to Make You Happy
- How I Roll
This song grew on me so much! The production on this is one-of-a-kind. - Quicksand
You can hear Lady Gaga’s vocals in the background. - If U Seek Amy
- Toy Soldier
- Showdown
- Scream and Shout (with will.i.am)
- Me Against the Music (feat. Madonna)
- Overprotected
- Work Bitch
- (You Drive Me) Crazy
- What It’s Like to Be Me
You can hear Justin Timberlake all over this track. - If I’m Dancing
A truly strange song - I Run Away
- Trip to Your Heart
- Someday (I Will Understand) (Hi-Bias Radio Mix)
- Slumber Party
- Just Luv Me
- Perfect Lover
- Change Your Mind (No Seas Cortes)
- Mmm Papi
Underrated, zany fun - Seal It With a Kiss
- That’s Where You Take Me
Wistful. - Radar
- He About to Lose Me
One of Kylie Minogue’s favorites. - Break the Ice
- Touch of My Hand
- Hard to Forget Ya
A 90s throwback that works! - Make Me… (feat. G-Eazy)
- Kill the Lights
- Up N Down
- Shadow
- Where Are You Now
- What You Need
- Don’t Cry
- Do You Wanna Come Over?
- Selfish
- Walk On By
This B-Side is stronger than most of the material on the Oops album - Passenger
- Hot as Ice
- Anticipating
- Liar
- Tom’s Diner (with Giorgio Moroder)
- Just Like Me
- Brave New Girl
As close as she ever got to sounding like early-80s Madonna - Brightest Morning Star
- Trouble
- (Drop Dead) Beautiful (feat. Sabi)
- Mona Lisa
“They want her to break down, and be the legend of a fall…” – 2005 - My Prerogative
- Criminal
- Unusual You
A lot of fans would kill me for ranking this song at #89. - Gasoline
- Mood Ring
- Body Ache
- Ooh Ooh Baby
- Perfume
- (I Got That) Boom Boom (feat. Ying Yang Twins)
- Before the Goodbye
Surprise! Teen-pop Britney collaborated with BT. - Pretty Girls
- Invitation
- Tik Tik Boom (feat. T.I.)
- Why Should I Be Sad?
As personal as Brit’s ever gotten on-record. - Don’t Hang Up
- It Should Be Easy (feat. will.i.am)
- Don’t Go Knockin’ On My Door
- Better
- I Will Be There
- Now That I Found You
A total Avicii ‘Wake Me Up’ rip-off. - When I Found You
- The Answer
- Don’t Let Me Be the Last to Know
- Do Somethin’
- Boys
- Mannequin
- Lace and Leather
- Get Back
How did this almost become the first single from Blackout? - Scary
- Big Fat Bass (feat. will.i.am)
- I’ve Just Begun (Having My Fun)
- I’m Not a Girl, Not Yet a Woman
- Sometimes
- Don’t Keep Me Waiting
- Rock Me In
- Out From Under
- SMS (Bangerz) (with Miley Cyrus)
- (I Can’t Get No) Satisfaction
- I Love Rock ‘N’ Roll
- Deep In My Heart
- Intimidated
- Outrageous
Extremely annoying chorus, beautiful MJ-style bridge. - Blur
- Early Mornin’
- Everybody
- Outta This World
- One Kiss From You
- I Will Still Love You (with Don Philip)
- When Your Eyes Say It
- Chillin’ With You (feat. Jamie-Lynn Spears)
Why? Oh, it’s sentimental… - My Baby
Why? Oh, it’s sentimental… - Rock Boy
Why? Oh, it’s — wait, why? - Chaotic
- From the Bottom of My Broken Heart
- Soda Pop
- You Got It All
- Dear Diary
- Private Show
A true, bona fide misfire - Autumn Goodbye
- Girl In the Mirror
- E-Mail My Heart
- Thinkin’ About You
- The Beat Goes On
- I’m So Curious
- I’ll Never Stop Loving You
- Heart
Just embarrassing! The end!
the american oracle 
I would have ranked “Toy Soldier”, “Mood Ring” and “Mona Lisa” higher on my own list but this was so interesting to read through, so many of these songs I even forgot existed!
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