The 40 Most Upsetting Moments From Britney Spears’ Career

RIP so many things that could have been SO GREAT.

1. The real actual GOOD “Perfume” video should have been released.

Britney Spears’ music-video-making legend Joseph Kahn called it one of her best videos of all time. WHAT!!

2. The full Dream Within a Dream Tour concert from Albany, N.Y., should have been put on DVD.

There are a few professional clips floating around from this concert that were aired in Japan. All of the clips feature ACTUAL REAL LIVE VOCALS (!!!).

3. The full “Outrageous” music video should have been completed, and the song should have been released as a single.

They should have shot some B-roll or something. That Snoop Dogg plotline is such a mystery.

4. Also that knee injury ruined EVERYTHING.

5. “Unusual You” SHOULD HAVE been released as a single.

6. “Freakshow” and/or “Toy Soldier” SHOULD HAVE been released as singles.

7. “Inside Out” SHOULD HAVE also been released as a single.

8. “Radar” SHOULD HAVE NOT.

9. “Radar” should have stayed on Blackout WHERE IT BELONGED.

10. “I Run Away” should not have been relegated to bonus-track status. It should have been on the Britney album.

Her best, most underrated ballad.

11. Basically, all of the Britney bonus tracks should have been on the actual CD.

12. Same with Circus and Femme Fatale.


“Selfish,” “Up N Down,” “Phonography,” and “Rock Me In.” YES, PLEASE.

13. Blackout should have been a No. 1 album. Fuck the Eagles.


Britney got screwed when Billboard changed their rules last minute to include sales from private retailers.

14. Kevin Federline should have never happened.

Frazer Harrison / Getty Images

Though we do love Jayden James and Sean Preston. Momney <3<3<3

15. Chaotic shouldn’t have happened either.

16. The full “Rebellion” should just be released already.

THEN EVERYONE CAN SHUT UP.

17. “Original Doll” should just have been released too.

THEN EVERYONE CAN ALSO SHUT UP.

18. The funeral scene from the “Gimme More” video needs to be explained.

Everything about “Gimme More” needs an explanation.

19. The early-2000s radio ban.


There is a rumor that Britney’s music was blacklisted from radio in the early 2000s. Basically none of her music from Britney charted on top 40 radio. “Slave” should have been a MASSIVE HIT!

20. “Break the Ice” deserved a proper video.


Ban that animated shit.

21. Britney deserved VMAs for “Toxic,” “Slave,” “Baby,” etc. It’s a joke that she won them for “Piece of Me.”


A lit’ral actual joke.

22. Also no. Just no.

Scott Gries / Getty Images

23. Britney Jean should not have been touted as “her most personal yet” because nope.

24. “Joy of Pepsi” deserved a proper single release too.

ICONIC EVEN IF IT’S A COMMERCIAL. SIT DOWN.

25. “And Then We Kiss” deserved a proper single release.


Also iconic.

26. NONE OF THIS.

Toby Canham / Getty Images

27. “My Baby.” No.

28. While now iconic, the 2007 VMAs should have been canceled.

Kevin Winter / Getty Images

29. Fred Durst.

30. Will.i.NOPE.

31. A “Breathe on Me” music video should have been made.

32. The fact that there are NO music videos featuring Brunetteney.

33. Her makeup artist.

Frazer Harrison / Getty Images

No more Raccoonney.

34. The skip in “Alien.”

35. Did I mentioned Will.i.CAN’T?!

36. The original concept for the Femme Fatale album should have happened.


Rumor has it, Femme Fatale was supposed to be an album filled with mid-tempos with a “hard hip-hop edge.” Then Dr. Luke got involved.

37. She should have kept “Telephone.”

38. In the past five years, Britney should have done a little bit of promo. JUST A LITTLE.


PROMO GIVES US LIFE.

39. There should and needs to be a studio version of “You Oughta Know.”

The most mysterious tour song of all time.

40. And lastly, they should have never broken up.

Kevin Winter / Getty Images

Sad but true. Sorry. Byeeeeeeeee.

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