Health & Medical Beauty & Style

The Worst Beauty Moments in Grammy History

The Wackiest (& Just Plain Ugliest) Hair & Makeup in Grammys History

When it comes to the Grammys, all ears are on the music and all eyes are on the red carpet. The annual awards show brings out musicians (and a few wannabes) dressed to thrill in some of the oddest get-ups imaginable.

And then, of course, there's the hair and makeup, which is where I focused my attention in pulling together the Worst Beauty Moments in Grammy History.

I've got some goodies here reaching all the way back to 1983 and an adrogynous Grace Jones in blue eyeshadow and a very strange hat indeed.

Then there's these goodies:

Wait til you see that one.

Oh and you won't want to miss Madonna in a gold grill making weird faces at the camera (see picture above). As a bonus, I include a gorgeous singer who walked the red carpet in braces, totally flummoxing me. You'll find out why. And please, help me solve that mystery.

I had a ball pulling this list together.

Let's start with the 2015 Grammys red carpet...

A Grammy Awards 2015 Worst: Madonna

Oh the squished boobs and the squished butt.

A Grammy Awards 2014 Worst: Izzy Azalea

The makeup was flawless -- I love that she kept her bottom lashes bare -- but Izzy Azalea's hair launched her on to the year's Worst list. Not a fan of the braided crown. Nope. And I wasn't alone.

A Grammy Awards 2014 Worst: Madonna

Madonna showed up at the 2014 Grammy Awards with a cane and this gold grill. The cane, I get (she had a busted foot), but the grill? Aiyiyi!

A Close Up of Madonna's Gold Grill

Here's the close-up shot you were dying for. Like teeth wrapped in gold.

She may have look freaky at that year's Grammys, but she's earned her spot at them. No artist has amassed more top 10 pop hits in the rock era than Madonna. Here's a look back at her top hits over the years: Madonna's 38 Top 10 Pop Songs.

A 2014 Grammys Worst: Cyndi Lauper

Cyndi Lauper makes this list a few times, most recently for her 2014 appearance in this strange red wig.

Cyndi Lauper is an 80s pop icon. Get the full scoop on her life and background in Cyndi Lauper - Profile of an '80s Icon & Singular Talent.

A Grammy Awards 2014 Worst: Katy Perry

 
Her makeup was flawless but that bun put Katy Perry on everyone's worst list that year.

Did you know that Katy Perry is the daughter of 2 pastors and grew up listening primarily to Christian music? Get the full scoop about her life in her About.com bio.

A Grammys 2013 Worst: Kerli

Look, whoever this "Kerli" girl is, is clearly smart. She knows that if no one has any idea who you are, you can easily get attention on the red carpet by showing up looking wacka-doodle-doo.

A quick Internet search shows Kerli is an Estonian singer who believes angels and fairies are a huge influence in her music. That said, she doesn't sound so odd in her interview with About.com's Top 40 music expert.

She talks about making it big at an early age in her home country and then moving to New York, where she feels free to express herself. She sounds quite lovely, actually.

A 2013 Grammys Worst: The B-52's Singer Kate Pierson

Three words: Next time Spanx.

More on Kate Pierson:
  • The B-52's hit song, "Love Shack" catapulted the band into fame. About.com's Pop Expert, Bill Lamb, named it the Third Most Popular Party Song of All Time. (See his list here). According to Lamb, the song "helped turn the band from the self-described, 'tacky little dance band from Athens, GA,' into arguably the world's top party band."
  • According to Lamb, Pierson reportedly lived in the house that inspired the song, "It did indeed have a tin roof and was the place the band conceived their first widespread hit 'Rock Lobster.'"


  • Although she has a history singing with the B-52's, Pierson is now known for her funky hotel getaway in New York's Catskill Mountains, Kate's Lazy Meadow.


A Grammy Awards 2012 Worst: Cyndi Lauper

Faith Hill made a few worst lists in 2013 for her bland makeup. One site actually dinged her for not wearing brighter lipstick, but bright lipstick would bring attention to the fact that Faith Hill is wearing braces here. 

Braces are totally cool for adults, of course, but what I don't get is why Hill ever needed them. You can clearly see in the photo on the right, taken at the 2008 Grammys, that Hill's teeth were PERFECT.

On the left, they are obviously gapped and odd and in need a good tightening via the braces.

Strange. If anyone can solve Hill's teeth mystery, email me.

Curious about Faith? Read her About.com bio and check out the Best of Faith Hill Playlist.

A Grammy Awards 2011 & 2012 Worst: Nicki Minaj

Cyndi Lauper simply has to make a red carpet statement and here she is in 2012 doing just that.

A Grammy Awards 2011 Worst: Hayley Williams of "Paramore"

Cue the Little Red Riding Hood jokes. Two years in a row, Nicki Minaj walked the red carpet in attention-getting costumes.

Don't miss About.com's Nicki Minaj Profile.

A Grammys 2010 & 2012 Worst: Lady Gaga

Hayley Williams appears to have been styled for the Grammys by an 8-year-old with markers.

Read more about her rise to fame.

A Grammys 2010 Worst: Beyonce

Aren't you glad you weren't sitting behind Lady Gaga at the 2012 Grammys? The Gaga wouldn't be Gaga without an outrageous costume and she didn't disappoint in either 2010 or 2 years later.

Did you know: Lady Gaga was born Stefani Germanotta in 1986? Find out more in About.com's Lady GaGa Biography and Profile.

2008: Guess Who?!

She is such a beautiful woman but the hippie earrings and those glitter extensions are wrong, wrong, wrong.

Beyonce, like me, is a native Texan. Get the full scoop on her life in her About.com bio.

A 2007 Grammys Worst: Imogen Heap

This apparently is not a female impersonator brought in from Vegas, but rather Cher at the 2008 Grammys.

Cher is no stranger to the Worst Dressed lists. In fact, she landed on my list, Oscars Beauty: The Worst of the Red Carpet a few times.

A 2004 Grammys Worst: Christina Aguilera

If you watched the Grammys in 2007, you likely have this image of English singer-songwriter Imogen Heap seared into your memory. Here's a flashback for you.

And while she looked wacky at the '07 Grammys, she didn't look much better 3 years later at the 2010 Grammys. See her get-up that year.

A Grammys 2002 Worst: Alicia Keys

Can you believe some Websites actually complimented Christina Aguilera that year for her "flapper look"? Hello!?!

Awful.

She may not be able to dress, but Aguilera can sing. Check out the Top 10 Christina Aguilera Songs.

A Grammys 2001 Worst: Christina Aguilera

This looks like a Halloween costume thrown together at the last minute from curtains found in the bedroom, not a proper Grammys outfit. Hopefully, Alicia Keys fired the stylist and the makeup artist responsible for this sari-inspired glittery eye encrusted mess.

She may have looked like a hot mess at that year's Grammys, but she went home with a whopping 5 Grammys that year, including one for Song Of the Year (for "Fallin'") and one for Best New Artist.

A Grammys 2001 Worst: Toni Braxton

When you have ginormous fake boobs, I guess you want to put them on display, curtained by your 100s of crazy braids ala Christina Aguilera in 2001.

A Grammys 1998 Worst: Lil Kim

This Richard Tyler dress got the Grammy fashion critics buzzing in 2001. It certainly left little to one's imagination. Apparently, even J.Lo cringed at Toni Braxton's get-up.

Read About.com's Toni Braxton bio to learn more about this R&B singer.

1998: Gwen Stefani and Carly Simon

Sometimes you gotta look wacko to get the attention you feel you deserve, right Lil Kim?

Lil Kim has a history of legal problems. See her mug shot from 1996 and find out what she was convicted for.

1997: LeAnn Rimes

The bad hair twinsies of 1998: presenting Gwen Stefani and Carly Simon!

I have a funny Carly Simon story from 2007 or 2008. I was shopping in a tiny boutique in NYC's West Village and so was Carly Simon and her son. She flitted about the store as if she owned it, chattering away to sales clerk as if they were longtime friends. Finally, after piling a bunch of products onto the counter and asking the sales clerk to deliver them to her address, which she gave and the sales clerk wrote down, the sales clerk asked, "And what is your name?"

To Simon's credit, she thrust out her hand and said warmly, "I'm Carly, nice to meet you."

Don't miss the Gwen Stefani bio and Carly Simon's bio. Here's an interesting fact I bet you didn't know: Carly's father is the Simon behind Simon & Schuster publishers.

A 1995 Grammys Worst: Annie Lennox

LeAnn Rimes before she got hot. The year she won Grammys for Best New Artist and Best Female Country Vocal Performance for her single, “Blue.”

Read her full bio on About.com.

A 1989 Grammys Worst: Paula Abdul

Annie Lennox in "Escape From Disneyland!"

The next year she would go on to win a Grammy Award for Best Pop Female Vocal Performance for her song "No More I Love Yous."

Read her bio on About.com.

A 1990 Grammys Worst: Caron Wheeler

The dress, the hair. In one word, "Oy."

Read Paula Abdul's bio on About.com.

A 1984 Grammys Worst: Cyndi Lauper

Soul II Soul Caron Wheeler at 1990 Grammy Awards looking all sorts of wrong. But her song with Soul II Soul, "Back to Life," was the hottest song of 1989, according to About.com's 80s music expert.

A 1983 & 1984 Grammys Worst: Grace Jones

Witness Cyndi Lauper in her "Girls Just Wanna Have Fun" glory days.

Liked This? Don't Miss My Worst of the Oscars & Worst of the Golden Globes

And here we have the adrogynous Grace Jones in wacky hats, bad brows and really bad blue eye makeup at the '83 and '84 Grammys.

Check out this interview with Jones on About.com.

If you liked the Grammys, you'll love the Golden Globes and the Oscars red carpets. Guess who this actress attending the Oscars is. Keep clicking to find out.

Don't miss the worst hair and makeup in my slideshows:


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