The MTV Video Music Awards are a category all their own. More casual than the Grammys, more sophisticated than the Kids' Choice Awards, and more outlandish than any of the awards, the VMAs became legendary in the 80s and 90s for their over-the-top performances. Some performers lean toward an edgy, minimalist style, while others nod to the show's roots in playful hair and makeup.

Below are some of the coolest beauty looks at the VMAs.

At the VMAs, billed as her first comeback in years, Britney Spears went all Britney with crimped hair, lip gloss, and perfectly applied black liner and eyeshadow. Her fans cheered her heartily for her appearance.

Every time you think you've seen everything Dodja Cat has to offer, she comes out with something even more avant-garde and bad*ss. The crystals strategically placed around her white eyeshadow are already cool, but her spider-like eyelashes are even cooler, matching the actual crystal spiders in her ears.

Bjork was marching to the beat of her own drum long before we caught up with her, including the signature bun hair that defined her style in the 90s. With dark eyeshadow and minimal makeup, I love this look.

"Voluminous blonde hair with visible roots, strikingly defined but subtle black eyeliner, and just a hint of color on the lips.

Gwen Stefani used to love decorative crystals. Combined with her blue hair in a bun, the look captures the edgy, feminine aesthetic that she excelled at in the 1990s. It suits her well, but is impossible to replicate.

Rizzo was at the 2022 VMAs in a huge navy blue gown (which almost matched the black carpet she was walking on). The lip ring and blue lipstick were just perfect for this over-the-top event.

Drew Barrymore very famously wore a daisy in her hair at the 1998 Academy Awards, but did you know that she wore the same style to the VMAs a few years earlier?

Considered one of the greatest rappers of all time, Lauryn Hill is also known for her unique style, and in 1999 she was impossible to miss (and literally glowed red) as she won four Moon Men Awards. The red shade is a cool Y2K touch that finishes the look.

Nicki Minaj has debuted some wild looks in her career, but I especially love this two-tone pink and blonde hairdo. The hair and lipstick match her Barbie pink dress, but the rest of her makeup is relatively simple.

Sinead O'Connor's signature bald head, now inseparable from her persona, was revolutionary (and semi-controversial) at the time. With a clean cat eye and a touch of lip color, she looks perfectly balanced and ready to rock.

Although she often exaggerates her hair color and styling, Billie Eilish also makes her minimalist beauty look striking. Her relatively new blonde hair, cut shaggy, was just deeply cool.

Aside from its "pastiness" (Lil' Kim's outfit infuriated some), the purple wig is genuinely very stylish. And she and Mary J. Blige both sport the same long lashes, dramatic eye shadow, and strategically placed lip gloss.

If you're going to reference a pop culture moment, go all the way. Katy Perry references Britney Spears and Justin Timberlake's double denim outfits.

There's a lot to unpack - this late 90s aesthetic defined our style for years - but the fact that everyone (except Posh) matched in blue eyeshadow is the first cute matching moment I think I missed. And they all have different lip colors.

We get great fashion and beauty from Taylor Swift, generally and when she switches things up at the VMAs. This 2019 look is more patterned and colorful than usual, and the bright red lip cleverly draws the eye up towards her face.

I've always been a fan of Alanis Morissette's style. She always leans heavily on gorgeous hair, and for good reason. This is a sophisticated take on her classic style, with long layers, but still with the traditional minimal makeup and natural beauty.

No list of VMA beauty looks would be complete without Miley Cyrus, whose aesthetic is constantly evolving. But the jump to short hair in a sky-high pompadour was the moment she realized she had gone from a teen to a fully grown woman.

TLC was not the first group to wear all matching outfits as part of their group "thing," but they were one of the best at it. Like Lisa's hair style, I appreciated how understated and mellow their makeup was, considering those wild crop tops.

Cyndi Lauper had a maximalist style that any 80s girl would want to emulate. Despite incorporating so many striking elements - dark lips, dark brows, dark eyeshadow, and a disheveled tease pixie that moves in all directions - Roper looks surprisingly put together.

First, I really love Megan Seastallion's choker, and it makes sense that she would style her look around that statement piece. Second, the striking contours and dramatic eye makeup complement the bones of the necklace and dress.

My '90s queen, Pamela Anderson, was in full swing here with long platinum blonde hair, pink matted lips, and dramatic black eye makeup. Bonus '90s points for that choker (and the fact that she makes her thin eyebrows look better than we do).

Technically, this is a post-VMA after-party, but Cher looks so stunning here that we have to add her to this list. The blonde pixie (her eyebrows are dyed accordingly), the lavender eyeshadow, the perfectly nude lips, the statement earrings and headband, everything looks great.

An important part of Shakira's trademark style is her long, voluminous hair (I always wish I looked like her - too bad). Here, highlights and long layers add depth and volume.

Rihanna's career has always been about style and incorporating makeup and hair into her looks (she was a makeup expert long before she launched Fenty). This combo of pixie, bold lashes, and red lips seems like a modern refresh of the 50s aesthetic.

Similarly, J.Lo has long had an iconic style and beauty look. This is from her early days at the VMAs (2000 to be exact) and is very on-brand for the Y2K aesthetic. Thankfully, her makeup is neutral and understated.

Courtney Love, who appeared on the legendary red carpet with partner Kurt Cobain and baby (they were literally holding a baby bottle) in tow, has to admit that she looks great here, too. Her red lips and soft waves of platinum hair look so classic.

Iman in a floral dress is a vision (David Bowie is her date-worthy enthusiasm). The deep wine-colored lip gloss is perfect, and paired with a similar shade of eye shadow, the model doesn't overdo it with the bold, dramatic look.

While everyone was (appropriately) focused on the literal flesh dress that Lady Gaga wore, I actually think her makeup looks great here as well. And, though I didn't realize it until this moment, her red lipstick matched the flesh on her head.

Cindy Crawford in belted Versace figuratively sealed off the red carpet (it was even rarer to see such startling designs than it is now), but her makeup and hair are not exaggerated, yet still subtle and matte. They don't fight with the costumes, but they are equally striking.

How about announcing to the world that she is pregnant during her performance at a major awards ceremony? Gentle blonde waves, nude lips, deep gray eyeshadow, all contrasted with a sequin-perfect outfit.

If you're going to wear snakes as accessories, your beauty look has to match. Britney Spears showed off her fabulous wavy hair and pink lip gloss, but (as always) we're drawn to the 00s-inspired glitter highlighter on her cheeks.

It's hard to beat the Queen of Pop. When Madonna took the stage at the VMAs wearing a "Boy Toy" belt over her wedding dress and singing "Like a Virgin," we were forever changed. And that red lip and messy, crumpled curls will go down in infamy as an unforgettable part of this iconic look.