There aren’t many artists that can boast as successful of a career as Madonna since she has become an icon in the world of music. She is revered as one of the most influential music artists in the world of pop music and is often referred to as the Queen of Pop. Yet, the most interesting part of Madonna’s professional life is the fact that the majority of her biggest hits were from early on in her career. Unlike other icons in the music industry, Madonna isn’t known for her stellar singing ability or the vocal acrobatics that she can perform with her voice. Instead, she often relies on the shock factor she can muster up and the attention she can grab from the media regarding her over-the-top hijinks.
Like any other musician that got their start over more than just a few years ago, Madonna has had to evolve to try and remain current in the eyes of the public. In her efforts to try and stave off the signs of aging and appear more than just a washed up/has-been, Madonna has done more than just evolve her look and style. She has actually gone through a series of different phases in order to try and stay on top of the latest trends and be known as the pinnacle of the pop world. While there were some stunts that seemed to work (like kissing Britney Spears on stage) and there were some looks that worked (like from her “Material Girl” days), there were a number of phases throughout her career that made her look downright ugly. Check out our list of the 15 photos of Madonna during her ugly phase and see how she has evolved over the years.
15 Spread Eagle Phase
Madonna has always tried to use her sexuality as a way to provoke the audience, get people interested in her as a performer and maintain her status as the Queen of Pop. From her infamous sex book to the various videos of her appearing stark naked, she’s never been opposed to appearing less than a traditional “lady.” Yet, there comes a time in every woman’s life when it’s time to close your legs (literally). While younger performers like Beyonce and Rihanna have performed a few spread eagle stunts on stage, the pose is often used in some sort of dance routine and isn’t really thought of as part of their performance. Madonna, on the other hand, has used the spread eagle stance as a way to try and provoke the audience in a shock factor manner. However, it doesn’t come off as particularly sexy. Instead, it is practically cringe-worthy and it just makes people think about how they really don’t want to see a 58-year-old woman with her legs spread open.
14 14. Grill Phase
In an effort to appear still hip, Madonna went through a phase where she donned grills on her teeth. Yet, this look was for more than just a music video. Madonna actually walked around with these grills on her teeth on more than one occasion. She walked the red carpet with them on and she attended as many hotspots that she could be photographed at during this phase. While it may have been a good look for a rapper trying to increase his street cred, it definitely wasn’t a great look for Madonna. The gold grills looked more like dirty teeth with a bit of shine rather than something costly that was trending at the time. Because she wore these during a time when her face was starting to show major signs of aging, the gold grills looked even worse than just decaying teeth. It actually made people think about dentures for grannies seeking out a bit of bling rather than the Queen of Pop making a comeback.
13 Hat Phase
Oftentimes, hats can be used as a fashion piece. While men’s hats have always been thought of more as utilitarian, women’s hats have been fashion statements that can create an overall feeling. From the glamorous turbans that Eva Mendes made into an entire look to the floppy sunhats that have become the go-to look for celebrities all over the world, choosing the right hat can be a great way for a woman to make or create her appearance. Yet, not everyone knows how to choose the right hat for their look. Just as Pharrell Williams made a fool of himself when he began his crazy hat phase, Madonna had a crazy hat phase of her own. She wore a variety of different hats during this phase, with all of them having a wide brim. She sometimes propped the hat at the crown of her head and other times she put a bit of a tilt on the brim. Yet, it didn’t exactly create a fashionable look. Instead, it looked like she was just having a bad hair day or trying desperately to look cool.
12 Skeletal Phase
Celebrities in Hollywood seem to always want to appear as thin as possible and this is particularly true for women. There never seems to be a weight that is ideal for a woman in Hollywood because there is always a weight that is thinner and more appealing. This shouldn’t be surprising in a world that thought Kate Moss was the epitome of beauty during the heroin chic craze, not to mention the plethora of size zero models walking the runway every year at Fashion Week. Yet, not everyone can pull off the skeletal look, which is exactly what happened to Madonna. While a younger woman can have the sunken cheek look and still appear beautiful, an older woman requires a firmer more plump look to her face in order to appear youthful. During Madonna’s heroin chic phase, there were a number of memes that were created comparing her to Gollum from The Lord of the Rings franchise. Obviously, that is not the character any celebrity would want to be compared to, especially in regards to appearance.
11 Baby Jane Phase
At some point in every blonde celebrity’s career, they tend to try their hand at the classic pinup look. From Gwen Stefani to Christina Aguilera, almost every platinum blonde has put a few pin curls in their hair and completed the look with some bold red lipstick. Yet, not everyone knows how to perfect this look. In 1988, Madonna went through a phase where she tried to look like a glamorous pinup girl but she didn’t know how to execute the look. She paired up the red lipstick with some deep purple eye shadow and her complexion looked ghostly white rather than a porcelain beauty. She wound up looking like a clown and worse yet, it made her look far older than she was at the time. For a woman that has spent the last decade doing anything and everything she could in order to not look old, it’s ironic that she would don a look that would age her far beyond her years early on in her career.
10 Too Much Hair Product
During the 1980s, there was a big hair craze that everyone of that time fell victim to, regardless of their status in fame or fortune. While the world could have forgiven Madonna for a teased hair look or even a bad poodle hairstyle from a crimping iron or a perm gone wrong, that wasn’t the case. Instead, she sported a long bob with an abundance of hair product that made her teasing efforts look absolutely destructive. She looked like her hair was thinning and the product caused the strands to stick together and stick out like Coolio antennas. This was right around the time of her Desperately Seeking Susan days and she didn’t just sport the look for the film. She actually posed for pictures with her hair styled this way. Perhaps she thought it was edgy or trendy at the time but it wound up looking more dirty than fashionable.
9 Crazy Bangs
During the ‘80s, there was a fascination with bangs that people just couldn’t get enough of for quite some time. The bangs were often styled into some sort of wave style that almost looked like a tunnel (or as close to a tunnel as a girl could get them). Yet, Madonna’s super thin hair and excessive use of hair product couldn’t get her to master the look. This coupled with the fact that she was not a natural blonde and had to constantly dye her hair, Madonna’s locks became completely fried from the processing and styling. Rather than creating the look of the times, she created a look of her own that was definitely not very appealing. She basically only had strands of frizz that stood completely straight up in the air and held there with a bottle of hairspray, no doubt. The combination of the frizz and the wispy strands made her look like she was desperately trying to achieve the big hair look but it wasn’t even trendy for the ‘80s decade.
8 Platinum And White
During the early part of Madonna’s career, she had a dirty blonde hairstyle but she changed her appearance right around the time when her 1987 film, Who’s That Girl, was released. It’s hard to say what was the worst part of this look since so much of it was all wrong. Not only was her complexion made painfully white to look like a ghost rather than a porcelain-skinned beauty but her eyebrows were practically jet black and way too bushy. Nowadays, bushier eyebrows are thought of as glamorous and necessary for achieving a perfectly contoured face. However, her eyebrows during that time was more than just filled out and perfect for framing her eyes. Instead, it looked like two hairy caterpillars were crawling across her face and each long hair stood out to look like legs. The bangs of this hairstyle were cut to the middle of her forehead and it made her look like a blonde version of Curly Sue rather than a glamorous blonde bombshell.
7 Dark Under Brows
Makeup styles have changed over the years but there are some fundamentals that have never changed. The general rule has always been that only one portion of the face should be highlighted at any given time. So, if the main focus is the bright red lipstick, the rest of the face should be subtle enough to let the lips be the star of the face. Yet, someone must have forgotten to tell Madonna about this cardinal rule in makeup application because she never got the memo. Instead, she went through a major phase where she seemed to highlight the entire face. From bright red lips to boldly defined cheeks to the most vibrant tones in eye shadow. While this is bad enough, she chose to use the darkest shade of eyeshadow directly under the eyebrows. While the smoky-eyed look is pretty trendy, it is created by highlighting the area around the eye rather than the top by the brow. This application made her look like she had even bushier eyebrows than normal and it made her further look like a clown.
6 Long Armpit Hair
The most feminine thing about a woman is the attention to detail when it comes to all the hairs of a woman’s body. From their hairstyle to curling their eyelashes to shaving their legs, a woman is often thought of as a work of art in the smoothness of her skin and the beauty of her eyes. Yet, Madonna went through a phase in 2014 that was more like a publicity stunt than anything that might be considered sexy. Posing in a skimpy black corset, she can be seen exposing her armpit with a full bush of hair. She posted the photo to her Instagram page with the caption, “Long hair…… Don’t Care!!!!!! #artforfreedom #rebelheart #revolutionoflove.” Madonna has previously stated that she used to let her armpit hair grow in her younger years and she even gave a 2011 interview with Harper’s Bazaar where she said, “The boys in my school would make fun of me.” While this is something that she may have thought of as empowering and rebellious, it was actually really unsightly. Is there anything more ugly than seeing the hairy armpit of a 55-year-old woman?
5 Channeling Bettie Page
Most people think of Madonna as blonde because it can be easy to forget that she was actually born a brunette. Her Italian background has given her naturally dark locks and she even went through an all-natural phase during the time around the music video, “Like A Prayer.” Her natural hair color is actually quite becoming on her, especially when it’s free of so much hair product and styling. Yet, in true Madonna fashion, she chose to completely overdo it and went through a phase where she not only dyed in completely jet black but she styled it in a way to try and imitate Bettie Page. While this iconic ‘50s pin-up may have been able to do the jet black and short bang look justice, Madonna doing it was like seeing a grandmother in a bad wig. It wasn’t the least bit sexy on her and it only made the wrinkles stand out even more on her face.
4 Black Shark Tooth Hairstyle
In an effort to try and evolve herself as a music artist, Madonna had to try something new to shed away from her ‘80s persona. While the teased hair and neon colors may have been alright for the ‘80s, she needed to try something different when she was planning the music video for her 1993 song, “Rain.” Yet, the visual was far from moving in the right direction. She traded in her dirty blonde locks for a sleek black bowl type hair cut, which can only be described as the worst wig in the world. Not only were the sideburns long, thick and overly wide but the bangs were cut like it had been worked over by a 2-year-old. The choppy bangs looked like jagged shark’s teeth hanging over her forehead and the jet black tone looked almost blue to coincide with the blue background of the music video. While it definitely showed that Madonna had changed from her signature ‘80s look, it didn’t quite hit the mark.
3 Matador Phase
It’s pretty clear that Madonna has a thing for the Spanish culture and the act of bullfighting. She reportedly championed herself to play the role of Eva Peron, the wife of the Argentine President Juan Peron, on the big screen. She also had a matador-themed music video for the 1994 single, “Take A Bow.” Yet, not everyone takes their personal interests so deeply into their clothing and the ones who do look like they’re wearing a costume. This is exactly what happened with Madonna during her matador phase. At the 2015 Grammys, Madonna showed up in a matador ensemble and to grab even more attention, she flashed her backside to the cameras on the red carpet. She also implemented a matador routine for her “Living for Love” video that same year. While she might find matadors intriguing, implementing them into her regular clothing options is more than just a little strange. Is there anything uglier than seeing a 50+ woman lifting her matador skirt to reveal her sagging butt cheeks being held up by two black straps?
2 True Blue Phase
When Madonna went through the platinum blonde hair phase, many people thought that it looked the best when when it was at its shortest. This was when Madonna was going through her whirlwind romance with Sean Penn and the world fell in love with her pixie cut hairstyle. It made her look young, happy and completely in love. Yet, she didn’t always know how to style it once it started to grow out. This became blatantly clear during the music video for the 1986 single, “True Blue.” While the cover turned out pretty great for the True Blue album, the music video is cringe-worthy. She chose a hairstyle that was short on the sides and long on top. While the top and sides had a bit of a curl to it, the back was swept together in a straightened style that reminded people of an old country singer rather than the Queen of Pop.
1 Everything And The Kitchen Sink
Over the years, Madonna has partook in a number of over-the-top stunts to try and remain in the spotlight. From a bejeweled headdress to cones on her breasts, she’s never been a wallflower when it comes to trying to stand out and get people to look at her. Yet, her overall look at the Met Gala in 2016 was even more than what the world is accustomed to when it comes to Madonna’s red carpet antics. She threw all of her tricks into the same hat with this look, from see-through lace to duct tape over her revealed nipples. This isn’t the first time she’s revealed her backside on the red carpet and it’s also not the first time when she’s used help from the clothing material to lift her butt cheeks. This phase of “Look at me, look at me,” has always been around with Madonna but it’s never looked so desperate than with this particular ensemble. Her makeup look painted on and she made sure to complete the look with an extra large jeweled headdress to adorn her forehead. This might be the ugliest phase of all since it doesn’t seem to be going away anytime soon and who knows whether or not it will get worse.
Sources: New York Daily News, Rolling Stone
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