10 Celebrity Makeup Transformations That Completely Backfired

Since they often enjoy the benefit of professional glam squads to primp and paint them like a Renaissance portrait, it's no wonder that disastrous celebrity makeup transformations are often well documented as cautionary tales. Unfortunately, all the money and success in the world can't save celebrities from dubious concealer trends and the wrong shades of lipstick that make a look go down in flames. With great power comes great responsibility, but even the most striking beauties in Hollywood can't always serve the best makeup looks.

Celebs like Kelly Osbourne, Nicki Minaj, and Tyra Banks have strutted down highly photographed red carpets in makeup that have made fans do a double take — and not in a good way. From mismatched foundation to wild eyeshadow and powder flashback galore, these celebrities have suffered through some makeup transformations that have completely backfired.

As someone well known for her role as a harsh style critic, fans expect aesthetic excellence from Kelly Osbourne, who hosted E!'s "Fashion Police" alongside other notable fashion figures like Joan Rivers. Her reputation for giving biting commentary on other celebrities' looks makes her makeup blunder all the more detrimental.

In 2012, Osbourne arrived on the red carpet of an Art of Elysium event wearing a foundation shade that looked startlingly yellow on her skin. It's a common makeup mistake to apply a foundation that is a shade too light or too deep for one's complexion, but to choose a foundation color so drastically different from the natural tone of her skin was nothing short of a tragic mistake, especially for a red carpet event. To make matters worse, the mishap with Osbourne's makeup didn't stop at the foundation. Her baby pink lipstick stood out for all the wrong reasons, and in the absence of a lipliner, Osbourne's lips appeared too undefined, yet too oddly vibrant at the same time.

To avoid making similar mistakes, these simple tips for checking your skin's undertones help you choose a shade that isn't too red, too yellow, or too olive for your complexion. Also, be sure to assess a foundation shade in natural lighting to ensure the color is comparable to your natural skin tone.

Lady Gaga has had many different looks, and is known for pushing the envelope when it comes to makeup and style. Her fashion choices have been both iconic and controversial, like her raw meat dress for the 2010 MTV Video Music Awards, which sparked outrage, interest, and discussion regarding the dress' deeper meaning. Gaga's adventurous nature extends into her makeup choices, many of which pay off, like, her 2019 Met Gala look featuring outrageously long and artfully crafted false eyelashes. However, there are some makeup transformations in Gaga's style history that just didn't land, such as her 2009 MTV Video Music Awards graphic liner flop.

For both her appearance on the red carpet and her performance during the event, Gaga wore intense, black graphic eyeliner that was meant to give drama and artistry, but translated as sloppy and uninspired. Attempting to pair a cutting black liner look with a smoky eyeshadow application came together to make a jagged mess with barely visible glitter. The look appeared even more unkempt with the flashback created by a non-camera-friendly setting powder likely made with silica, which is a known flashback culprit. Couple all these mistakes with a practically non-existent lip combo, and you have a look that falls far from its artistic, cutting-edge aspirations.

Crafting a perfect graphic eyeliner look can be a challenge, but keeping things simple and clean-cut can offer the most flattering results. Avoid overpowering eyeshadow and glitter when planning these looks, and let the liner do the talking.

Nicki Minaj went through the makeup wringer in the early 2010s with her bright, dramatic, and excessively contoured looks that didn't always translate well in photographs. This era of Minaj's makeup is known to fans as her "Harajuku Barbie" phase, with ”Harajuku" referring to the aesthetic associated with the Harajuku neighborhood in Tokyo's Japan, which is a district historically known as a hub for art, fashion, and self-expression. Some distinctive features of this style include exaggerated or doll-like makeup, including intense eye makeup and contouring.

Minaj's application of Harajuku influences often left much to be desired in terms of technical application, and she faced a world of makeup ire when she attended the 2011 American Music Awards Nominations wearing a myriad of makeup faux pas. Even taking into consideration the aesthetic context and influence of the look, Minaj's makeup for this event went beyond explanation. Her contour was heavy-handed and unblended, featuring a thick pale strip down her nose. Her concealer was much too light and gave her a sickly appearance in photos, and in conjunction with being over-baked, the upper half of her face ended up a completely different color than the lower half, save for the stark dark lines of her nose contour. Her eyes were also disappointing, with eyelashes that were spidery and awkward, and her bare under eyes gave her a massively unbalanced appearance. Finally, her bright lipstick was unlined and haphazardly applied. For a more balanced, blended look, consider these tips for choosing the right shades to contour with, according to a makeup artist.

High-definition photography and camera flash have historically revealed the worst of celebrity makeup mistakes to the public. Even some of the most stunning stars in Hollywood aren't safe from the dreaded flashback caused by silica setting powers; like Angelina Jolie's worst makeup mistake of applying setting powder with silica before attending the premiere of "The Normal Heart" in 2014. 

Miley Cyrus suffered a similar fate on the red carpet of the 2013 Maxim Hot 100 Party. To be fair, makeup formulation and photography technology don't always advance at the same pace. As cameras increase in definition and flashes get brighter, sometimes makeup artists and celebrities are unpleasantly surprised to see how they interact with one another. Unfortunately, Miley Cyrus discovered how detrimental flashback can be for an otherwise clean-cut look at the same time as the public. The haze of white powder around her mouth gave her the appearance of a ghostly white beard, which deemed this look as one of Miley Cyrus' biggest makeup fails of all time. The powder was likely added to her chin area to set her liquid makeup and control shininess from the skin's natural oils, but the application of the wrong product made a much worse impact than an oily chin.

To avoid flashback, make sure to check the ingredients of your setting powder of choice. Silica is an additive intended to absorb oil and give the skin a smooth, blurred effect (which it does in natural lighting or in person), however, silica is highly reflective, which makes it unsuitable for flash photography.

During life's difficult moments, it's hard to focus on the little things. Unfortunately for Lindsay Lohan, some of her most tragic days are caught on camera, and those photos and videos revealed she wasn't looking her best during her multiple trips to the courthouse. During a 2011 court appearance for continuously failing to complete her mandated community service hours after her shoplifting conviction earlier that year, Lindsay Lohan displayed a horrific contour application that left viewers shocked.

This courthouse contour mishap is a combination of multiple common mistakes. First, the product chosen for the task was the wrong color. Yes, a true contour shade should be cool-toned. Unlike bronzing, which adds soft dimension and glow by adding warmth to the perimeter of the face, traditional contour should be applied with a cooler-toned product to avoid muddiness and emulate natural hollows, but just how cool-toned the product should be depends on the wearer's undertones and depth of their complexion.

Since Lohan is naturally fair, a gray-looking contour shade could be appropriate when applied correctly, which leads to the next issue: over-application. Creating shadows on the face requires a light touch. Lohan densely applied a product that wasn't meant to be concentrated in one area, let alone in the wrong area. On the topic of misplacement, contour shades belong where shadows occur on the face: hugging the bottom of the cheekbone or under the jawline. Lohan applied the product in a stripe a great distance below her cheekbones, giving her face a sagging appearance.

It's hard to believe that someone now recognized as a makeup mogul suffered an unfortunate cosmetic transformation, but everyone has their off days. In 2010, while attending the NRJ Music Awards, Rihanna took to the red carpet with under-eye concealer that was many shades too light for her complexion. Though well blended into the rest of her complexion products, the startlingly light under-eye section of her makeup threw off the harmony of her look.

During the early to mid-2010s, ultra-bright concealer under the eyes was a popular method to combat the appearance of under-eye bags, combat tired-looking skin, promote radiance, and draw attention to one's eye makeup. Subtler variations of this trend have been utilized in the decade following its peak, especially in high-glam looks and makeup meant for the stage. However, going back in time, many applications of this method were overdone, leading to an unbalanced, unnatural, overly lightened under-eye.

To achieve that bright, luminous, well-rested under-eye look, consider using a concealer shade one to two shades lighter than your natural skin tone or foundation shade. The change should be subtle, but the effect is clear in person and on camera. To combat hyperpigmentation in the eye area, a color corrector could help. These products use color theory to cancel out the hues that naturally occur in the delicate skin around the eyes and mouth. Color-correcting can be tricky, so consider reviewing these tips to avoid common color-correcting mistakes.

Drew Barrymore suffered a few makeup mishaps during the press circuit and premieres of "Charlie's Angels: Full Throttle" in 2003. At the U.K. premiere, Barrymore suffered through one of the worst instances of flashbacks on a red carpet. Nearly the whole upper third of her face was covered in reflective powder around her eyes, cheeks, temples, and even in her hairline, giving her blonde locks a white cast. In some photos, the flashback is so prominent that it almost looks like a deliberate, albeit questionable, aesthetic choice. In other shots, however, it's clear that it's a settling powder and not a white pigment applied like a swath of artistic eyeshadow.

Unfortunately for Barrymore, the makeup conundrums didn't stop there. During a press conference for the same film in Australia, Barrymore sported yellow eyeshadow that left viewers scratching their heads. The application of the vibrant shade went from the outer corner of her eye, over the lid, and into the inner corner. A monochromatic eyeshadow look with a vibrant color can be stunning when applied with good technique, but Barrymore's sloppy paint job made it look shabby and unintentional. To make matters worse, she added a bright red lip.

When constructing bold makeup, balance is essential. A colorful eye is best paired with a neutral lip. This balancing method allows a viewer's eye to focus on a singular striking aspect of a look rather than having one's attention drawn to two competing focal points.

Tyra Banks' 2012 Moth Ball makeup look is one that will go down in infamy as an unhinged makeup transformation. The model wore a wild, unsymmetrical application of smoky black eyeshadow up to her lightened, barely-there eyebrows, and accented the look with hardly noticeable gold in her inner corners and on the lids. Noticeably absent are a pair of false eyelashes to frame the eyes because, despite the egregious use of black eyeshadow, the eyes still seem strangely bare without lashes. Beth Shapouri from Glamour described the look as "the most terrifying yet completely hypnotic eye makeup I've ever seen in my life," which checks out. Banks completed this harrowing look with an application of equally startling fuchsia lipstick, which seemed quite out of place considering the color wasn't tied into any other aspect of the makeup or outfit.

Bold, smoky eyeshadow can be difficult to achieve without the proper technique and preparation, so it might be a good idea to read up on common smoky-eye mistakes before dipping into the black eyeshadow. In regard to Banks' look, a more concentrated, less blown-out application would have made the makeup more wearable. Adding eyelashes to give structure and frame the eye would give a more sultry effect, and changing the lip color to a neutral shade would promote balance and allow the viewer's eye to focus on the striking aspects of the makeup on the upper third of the face.

To reiterate, selecting the correct foundation shade is necessary for achieving a flawless, your-skin-but-better makeup look. Mistakes at the literal foundational levels of a makeup application can ruin the whole look, so taking the time to check your shade in natural lighting is a must to ensure that the transition from makeup to skin is seamless. Ariana Grande did not take this rule into account when she attended the 2015 American Music Awards wearing a foundation shade that was multiple shades lighter than her neck, and the rest of her body, for that matter.

This slip-up is one of Ariana Grande's most memorable makeup fails since the variation in tones was obvious, especially on camera, which can be especially unforgiving when compared to seeing the mistake in person. Grande's much paler face distracted from her otherwise well-done makeup look, giving her an overall disjointed appearance.

Matching one's face foundation to one's neck shade can be especially difficult for those who use self-tanning products meant for their bodies but don't use face-safe products to carry the deepened color upward. Avid self-tanners keep a foundation shade that matches their neck and body, despite it being a few shades too dark for their tan-free face. This practice may work for those who can keep multiple shades of a foundation on hand, but in a pinch, bronzer and contour can be used to deepen and warm up a too-light foundation shade.

While attending the White House Correspondents' dinner in 2010, entrepreneur and reality star Kim Kardashian arrived wearing a makeup that seemed a bit too one-dimensional. The star's makeup troubles were rooted in the fact that she over-powdered and over-baked her under-eye area, which emphasized her fine lines and sucked any plumping moisture out of her skin.

Baking is a useful method brought into the modern makeup world by drag queens, wherein a thick layer of setting powder is applied over cream or liquid makeup, primarily in the under-eye and T-zone areas and left to rest for minutes at a time to ensure that the makeup underneath is cemented in place. After the baking process is complete, the excess powder is swept away with a soft, fluffy brush, revealing a smooth, flawless, and sweat-resistant look. This application is perfect for performers who are engaging in dynamic, high-energy shows under bright, hot stage lights or in tightly packed quarters that might promote sweating. Some celebrities like Kim Kardashian have adopted the practice of baking their makeup to assist with longevity; however, over-baking is a risk to consider when applying this method to an average, or even "glam" makeup look.

Over-baking occurs when the thick layer of setting powder are left on an area for too long. The powder absorbs too much moisture and clings to the skin, emphasizing lines and texture. Such is the case for Kardashian's White House dinner look.