Amy Winehouse, Biggest Celeb Beauty Train Wrecks of All Time

Hairstyles

Biggest Celeb Beauty Train Wrecks of All Time

These stars have earned themselves a one-stop ticket to the beauty hall of shame thanks to their awful celebrity hairstyles and more

May 20, 2010 | by Anna Jimenez | 66 COMMENTS

Amy Winehouse

Winehouse has been a well-documented mess for quite some time now. Evidence: she already has a permanent spot on our Worst Hair Trends of All Time list.

While she deserves mad props for her voice and artistic prowess (she really is a great musician), that doesn't mean we can't point out that there is an alien pod living on top of her head. Some retro hairstyles are totally cute and fun, like these, but Winehouse's beehive is just too too much.

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These made me laugh!

by Only1KimmieD Wednesday, September 12, 2012 at 01:00PM Report as inappropriate

mother of god....

by michellefuentes Friday, August 24, 2012 at 06:34PM Report as inappropriate

Some of these female celebrrities would look SO much better if they just took a hot shower, scrubbed their faces, and washed their hair. No amount of plastic surgery, expensive makeup artists and hairstylists, fake-n-bake tans, and/or designer duds can make them beautiful unless their personal grooming habits improve. Don\'t these ladies have stylists, or at least a good friend honest enough tell them how terrible they look? It\'s worth noting that some of these women have substance abuse issues. There\'s a lot to be said for looking healthy and fresh, no matter what your age is.. Kate Middleton is a perfect example of this.

by BengalsGal Tuesday, August 21, 2012 at 12:37PM Report as inappropriate

For Amy, Liza, Lindsay, and Courtney, the problem is not about train-wreck hairdos. They have given their lives/souls to drugs and alcohol. The train wreck is their psychological well-being. Hair means nothing when your soul is gone. And we lost a woman with a true gift from God because of it - Amy. Where are there friends? Where are people who truly care about them? I think Ke$ha and Britney have psychological problems, too. There self-esteem is so low, they resort to thinking trailer park chic is good. Instead of seeming sexy and talented, they seem like tramps. These women have become the way they are by allowing us, the public, to tell them who they should be and what they should look like. I'd rather focus on the positive.

by Cheryl5752 Thursday, August 16, 2012 at 07:19PM Report as inappropriate

omg chill out, everyone. this article is just saying on certain occasions how bad these celebs looked. this means amy, britney, tyra, etc. lindsay, cher, and heidi are bad all the time because of their plastic surgeries. but no need to get your panties in a bunch.

by alexa112277 Sunday, August 12, 2012 at 03:56PM Report as inappropriate

I did not like this article at all. First of all, I strongly agree with many previous commenters that it is in extremely poor taste to mock Amy, even if this was written before her death, those who chose to reuse this article are still responsible. Besides that, these are all grown women! Their appearance is their business! And some of them are clearly very sick. I don't know Heidi personally, and I don't claim to, but I think she must have some BDD. I'm willing to bet the picture of Courtney you used as an example was before she got clean, and Lindsay is a well known drug abuser. This whole article leaves a bad taste in my mouth. Very dissapointing, Total Beauty.

by missmadeline Saturday, August 4, 2012 at 06:13PM Report as inappropriate

I agree with removing Amy or don't you people know!

by hoppersjj Saturday, August 4, 2012 at 12:42AM Report as inappropriate

You guys should remove Amy from this list!

by rachel_harville Friday, August 3, 2012 at 01:10PM Report as inappropriate

poor Amy

by LittleBunny Tuesday, July 31, 2012 at 07:05PM Report as inappropriate

I agree with Robyne about taking out the page on Amy...no comment on the others. You know, the old saying about having nothing good to say....

by alictasia Saturday, May 26, 2012 at 05:03PM Report as inappropriate

Time to remove Amy Winehouse ...

by robyne00 Saturday, May 26, 2012 at 04:30PM Report as inappropriate

I agree with all but Tyra!! I still believe that she looks fabulous!

by Pinkeebler Monday, May 14, 2012 at 12:27PM Report as inappropriate

These chicks are depressing

by TBjunkie Tuesday, April 17, 2012 at 12:01AM Report as inappropriate

Oh god..

by eatinglipstick Tuesday, April 3, 2012 at 08:04PM Report as inappropriate

Poor Lindsay...She looks so much worse now. She used to be a beautiful girl until the recent plastic surgeries she's had.

by powerwoman033 Sunday, March 11, 2012 at 09:08PM Report as inappropriate

Bleh....... Recycled crap. Read this before.

by queeniemeanie Monday, March 5, 2012 at 01:40PM Report as inappropriate

Amy should be left to rest in peace. Not called a train wreck. Very poor taste.

by tigerlily5 Sunday, March 4, 2012 at 08:13PM Report as inappropriate

Looks like they've recycled an old article, very common practice on media sites. Couldn't they have updated the entries first though? I still agree with Lindsay Lohan's inclusion on this list though. There is a beautiful girl under there, but she keeps messing up what nature blessed her with by tanning herself orange, starving her curves away, and dying her hair a color that does not suit her complexion at all.

by elph37 Sunday, March 4, 2012 at 12:39PM Report as inappropriate

Honestly, Lindsey Lohan needs some major help.

by peachtone Saturday, March 3, 2012 at 07:07AM Report as inappropriate

I agree with lavendargoose...Tyra's hair style was from some years ago..Amy shouldnt be on this list shes dead. I dont always see having plastic surgery equal to low self esteem. I think if a person see something and wants to fix it be it one or 10 thats what makes them feel better. I have (in my mind) high self esteem but if I can raise my boobs then I will.

by odie Friday, March 2, 2012 at 06:45PM Report as inappropriate

Pretty sure that this is a repeat of an old article, so Amy wasn't dead when they originally wrote this. But they should pay attention to what they are posting currently, and maybe COME UP WITH SOME NEW MATERIAL.

by lavendargoose Friday, March 2, 2012 at 01:49PM Report as inappropriate

Ok, picking on a dead person is not nice. RIP Amy.

by liz0822 Friday, March 2, 2012 at 12:07PM Report as inappropriate

I totally agree about Courtney, she is scary! As for Cher, I love her sense of style. She has paid her dues and if she wants to have plastic surgery and oddly colored wigs, then more power to her! : )

by WiccanLady Friday, March 2, 2012 at 11:28AM Report as inappropriate

it's amazing how much style has changed in so short a time

by sportimonki13 Tuesday, February 28, 2012 at 01:50PM Report as inappropriate

Funny article. lol

by yestfl Friday, February 24, 2012 at 01:06PM Report as inappropriate

Yikes!

by Coffee_Black Friday, January 27, 2012 at 06:52AM Report as inappropriate

I enjoyed it, haha :)

by patricia89 Wednesday, January 4, 2012 at 04:34AM Report as inappropriate

Haha :)

by MysticMeercat Saturday, October 29, 2011 at 08:43PM Report as inappropriate

you know, heidi montag looks like joan river's estranged daughter

by gisellemarie Wednesday, September 14, 2011 at 06:24AM Report as inappropriate

This article made for a good giggle :)

by PorcelainHeart Thursday, August 25, 2011 at 12:38AM Report as inappropriate

Tese are just terrible.. Courtney when will you learn?

by itzelc18 Monday, August 15, 2011 at 10:30PM Report as inappropriate

oh courtney...

by Bon_Bon Monday, August 15, 2011 at 12:13AM Report as inappropriate

It was fun to read!! We all can laugh when we look back. Nice article for a Friday

by sexysaydie Friday, August 5, 2011 at 09:22PM Report as inappropriate

sick and wrong.

by MissPurple Wednesday, July 13, 2011 at 02:08PM Report as inappropriate

Yuck. Those are just sad.

by LittleBunny Saturday, July 2, 2011 at 03:14PM Report as inappropriate

What fun.

by Agrimony Tuesday, June 14, 2011 at 03:13PM Report as inappropriate

I think these are all awesome :) and they are all favorites of Drag queens too!

by AKGALnIowa Tuesday, June 14, 2011 at 11:47AM Report as inappropriate

Oh, c'm on! They were ALL SO YOUNG in the 80s! Can't we forgive them (us)? Hasn't anybody got a photo taken during a marriage party during 1985? Prom dress and hairstyle? Gimme a break... Of course style has changed and we all have grown old and wise. But, we were so young!!!

by monicasacco Saturday, May 21, 2011 at 03:38PM Report as inappropriate

tyra's still gorgeous even if her hair is a little crazy

by cmiller63 Saturday, May 21, 2011 at 04:57AM Report as inappropriate

With all of the money they have, they can still manage to look awful? Jeez.

by LipglossandSpandex Wednesday, May 18, 2011 at 09:52PM Report as inappropriate

liza looks like a plastic grey ghost doll ich

by lelalu100 Tuesday, May 17, 2011 at 07:13PM Report as inappropriate

These looks are just plain scary!

by benbri1 Tuesday, May 17, 2011 at 01:07PM Report as inappropriate

I think Cher looks great in my opinion.

by socketpinch Tuesday, May 17, 2011 at 12:59PM Report as inappropriate

I'm glad they mention Britney

by porsha_coleman_mcdaniels Thursday, May 5, 2011 at 01:25AM Report as inappropriate

WHO LETS THEM OUT OF THE HOUSE??

by LittleBunny Wednesday, May 4, 2011 at 07:10PM Report as inappropriate

.. EW.

by yckitsmary Saturday, April 9, 2011 at 02:25PM Report as inappropriate

Some of these made me laugh a little inside and some of these... scared me.

by mkgx7 Saturday, April 2, 2011 at 04:15PM Report as inappropriate

you can never make me stop loving courtney love! as a kid in the early 90's (in seattle), my brothers forbade me from listening to the spice girls and made me into a Hole girl instead. and the whole riot grrrl ideology was helpful to me as a teenager. so yes, on the beauty front courtney love fails, but that's kind of the point!

by rachel_bo Friday, April 1, 2011 at 09:22PM Report as inappropriate

Kesha is a big train wreck.

by ebbsandtides Friday, April 1, 2011 at 09:05AM Report as inappropriate

Ke$ha PERMANENTLY looks drunk/tired/messy, can't she pull herself together?

by liliofthevalley Wednesday, March 30, 2011 at 12:51PM Report as inappropriate

Oh Kesha...u r a piece of work, Im still rooting for you girlie, Love Joan because she knows she is a HOT MESS

by Akinom Wednesday, March 30, 2011 at 01:32AM Report as inappropriate

It's always funny to me that celebs like Kesha that go for the 'I'm not trying' look are actually spending quite a bit of time achieving that look. That messy hair and eyeshadow actually takes time to do! (waste of time if you ask me)

by MeghanL Tuesday, March 29, 2011 at 03:48PM Report as inappropriate

oh Courtney...

by makeupbyjanalyn Tuesday, March 29, 2011 at 09:24AM Report as inappropriate

Liza Minnelli totally redeemed herself in Arrested Development and Sex and the City 2. I wouldn't say being eccentric makes you a train wreck.

by mlenaei Tuesday, March 29, 2011 at 09:03AM Report as inappropriate

honestly, i have to admit that it is kind of the publics fault for always pressuring them (ex. jessica simpson. she loses weight and people criticize her for being anorexic. she gain weight. people call her fat. she can never win!) but i have to agree. in this world, we have "standards"

by twinkledimples Friday, February 25, 2011 at 10:48AM Report as inappropriate

none of them are pretty

by judyangel101 Friday, February 18, 2011 at 07:20PM Report as inappropriate

that might be the most normal-looking picture of kesha i've ever seen.

by FIRSTand15 Thursday, February 17, 2011 at 03:29PM Report as inappropriate

Lindsay Lohan has so much natural beautiful...very sad

by LittleBunny Thursday, February 17, 2011 at 02:05PM Report as inappropriate

Lindsay Lohan used to be so beautiful. Such a shame.

by emmabeauty Thursday, February 17, 2011 at 02:24AM Report as inappropriate

ugh Courtney love... you will forever go down in history for looking like you just left the house fo the rising sun...

by Bon_Bon Thursday, February 17, 2011 at 12:21AM Report as inappropriate

Courtney Love...just wow.

by LittleBunny Monday, February 14, 2011 at 07:39PM Report as inappropriate

It's not "shoe-in" (which makes no sense on the face of it); it's "shoo-in".

by ButAnEgg Monday, October 4, 2010 at 03:03PM Report as inappropriate

Ok, Lindsey Lohan looks like she's a 60 year old who's trying to look like 17. Wow...that's rough.

by susie84 Sunday, June 13, 2010 at 02:20PM Report as inappropriate

I think there is too much pressure to look and be perfect so that is why she considered doing all the plastic surgery. If she wasnt in such a spotlight she wont if gone so drastic. Sad, but true.

by hkrnpma Monday, May 24, 2010 at 12:54AM Report as inappropriate

eesh. kind of scary.

by tonybaloney Friday, May 21, 2010 at 07:38PM Report as inappropriate

Definitely true that it must be hard to look good all the time when you're getting your picture taken at any and every hour of the day. I read the other day at Beauty Undercover about a couple too many lip injections... a bad hair day is one thing, but when it comes to surgery and injections, maybe take some more time to contemplate this bigger decision.

by laurapeper Thursday, May 20, 2010 at 11:48AM Report as inappropriate

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