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Celeb Embarrassing Photos: Madonna

| Filed under: MadonnaPhotos!


It happens to all of us!

CLICK HERE for a photo gallery of some embarrassing and hilarious photos of Madonna!

CLICK HERE for a photo gallery of some embarrassing and hilarious photos of Madonna!

CLICK HERE for a photo gallery of some embarrassing and hilarious photos of Madonna!

[Image via WENN.]

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32 comments to “Celeb Embarrassing Photos: Madonna”

  1. 1

    What's going on with the eyebrows ? It's called bleach

  2. 2

    once a person has been tortured, the victim is empowered, in a way, to disolve the law in his eyes

  3. 3

    Yeah, Shes a tranny. She has to be. Either she was born a male or she has testosterone injections to stay looking young.

  4. 4

    OHMAGAWD! It looks like something out of Alice in Wonderland, the Tim Burton version!!!! D:

  5. 5

    Re: NookiesWA – shut up delusional.M in the 90s was gorgeous.M in confessions era is gorgeous.

  6. Low says – reply to this


    He looks like a 8 year old and a 40 year old both at the same time. Very odd.

  7. Low says – reply to this


    oops. sorry.

  8. 8

    She still looks better than Mario lolz

  9. 9


  10. 10

    One of her more hidious looks. Big black eyebrows with bleached hair. Ugly. Glad that didn't last long.

  11. 11

    Re: NookiesWA – Are you allowed to cross the street unsupervised? Because I don't think you have enough brain power to pull a feat like that off without getting run over by a truck. Idiot!

  12. 12


  13. 13

    Re: MCiccone – Umm…that was Madonna in the 80s, not the 90s. Sheesh!!!!

  14. 14

    Um…. so these weren't even embarrassing??? Some candid shots of her eyes closed, her hair in front of her face etc… I was expecting her to pick her nose or scratching at her crotch to be justified as embarrassing!!

    Sorry this is the Queen of Pop we are talking about - u will have to be better next time and serve it up just as powerful as her!

  15. 15

    Hey Mary-o, People who live in glass houses, you know? Still a bully after all, I see.

  16. 16

    even looking her worst she still looks a million times better than your ugly ass

  17. 17

    In beggining of the 90s it was fashionable to have thick eyebrows, dark ones with lighter color hair. I honestly dont see nothing really bad, it was just the trend of the time. Todays Rihanna hair… tomorrow she will be lol too.

  18. 18

    What is embarrassing about it???? Holding an award is not embarrassing at all.
    Perez, I love you, but you have similar photos and they are not from the 80s. Your really bad hair photos are from 2009. :) :)

  19. 19

    People she was soo here beautiful ,don't be soo mean.

  20. 20

    She is Italian with natural dark hair like her daughter. Her eyebrows are the same color as her hair. That was the look back in the day. And many other artist had that same look. I really like her with her dark hair which she wore in Like A Prayer. But, she looks good Blonde or dark. JMO!

  21. 21

    whatever… happened to her!?

  22. 22

    there is not one embarrassing picture in there. perez your wayyyyy off the mark with these. all the pics show are her different looks throughout the years. also if having roots is so embarrassing most women are screwed. this was a dumb post perez. do some more research and give us a better quality posts.

  23. uyeah says – reply to this


    Platinum hair with black eyebrows. Could she or anyone around her not see how supremely ugly that was? She just had to lighten them halfway. I still cringe seeing her like that.

  24. 24

    Lmao. The only legit embarrassing photo is the default.Re: ChicagoBR – Lololol. Yea at least her bad choice of fashion was in style at that time.

  25. 25

    She was so beautiful.
    It's a shame she ruined her face with so much plastic surgery.
    Really sad, I used to have the worst crush on her.

  26. @v@ says – reply to this


    She was really fun to observe, and uniquely beautiful on top of that.

  27. 27

    Not really sure what year this was taken, but she looks a hot mess in this picture,.even for the time period she was in. Yellow teeth, dark bushy eyebrows, platinum hair…eww! This looks like right around her True Blue/Who's That Girl era, the period where she gave us her worst in some of her music and fashion. She has redeemed herself after that.

  28. 28

    I never thought she was an attractive woman. She definitely has musical talent, but I don't consider her beautiful. She's not afraid to be bold in her fashion, more power to her.

  29. 29

    What do u mean embarrassing?
    None of these photos are really that bad…just a trip down memory lane with our beloved Madonna.
    Love you M

  30. 30

    Re: NookiesWA – LOL!

  31. 31

    Perez, your low self esteem is showing again! Just b/c u look in the mirror and hate what you see doesn't mean you have to post "embarrassing" pic of another person.

    Let's see your embarrassing pics. Maybe you getting punched in the face or ur fat grill covered with acne?

  32. 32