The 32 Most Painfully ’90s Celebrity Photos of All Time

The 1990s gave us some iconic street style, classic movies, and inimitable superstars in the form of various models and actors—but it also gave us a lot of weird stuff. If you romanticize that particular decade (like I sometimes do), I'm excited to share with you some photos that will remind you of mullets, haphazard fashion, weird photoshoots, and a general casualness about being in the public eye. Our celebrities of the '90s weren't as fussy about where they were photographed, what they were wearing (a lot of them didn't have stylists, as you'll soon see), and what they were being asked to do. The results, I think you'll find, are as wacky as you imagine.

Below, 32 of the most painfully '90s celebrity photos of all time.

Madonna

Listen, Madonna tried a lot of styles, and not all of them worked! Here performing at Madison Square Garden, she's channeling the '70s in a way that feels a little on the nose (and clearly didn't take off, other than to serve as inspiration for Miley Cyrus).

Gwen Stefani

Gwen Stefani really gave us a lot of '90s grunge-indie-rock inspo, but I can't say I'm all that surprised that she didn't make these braids an essential part of her aesthetic. It's like Pippi Longstocking had an older, blonde sister. (Bonus: no thanks on the thin eyebrow trend.)

Mariah Carey and Rosie O'Donnell

One of the things I enjoyed ("enjoyed") about the '90s red carpet is that there were clearly no rules. On the left, Mariah Carey is headed to a fancy dinner. On the left, Rosie O'Donnell is headed to bed after a long day. And yet here they are, side by side.

Carson Daly and Jennifer Love Hewitt

The '90s red carpet was often an opportunity for celebs to pretend it was their prom—including their literal posing and formal outfits (all that's missing is a corsage here). Also, I wholly forgot how many famous actresses Carson Daly dated in the '90s.

Halle Berry

Oh, Halle. Before she went on to have a very stylish multi-decade career, she was just hanging out at the MTV Movie Awards with a boatload of fringe on top and regular-degular jeans on the bottom. The '90s red carpet—more casual than you remembered.

Britney Spears

Britney Spears was just hitting her stride in the late '90s, so this "deer in the headlights" situation is probably more a consequence of being a relative newcomer on the red carpet, but some part of me feels like she got out of her ride and wasn't ready to have her photo taken.

Christina Aguilera

We really loved fringe in the '90s. And knit. And ponchos. And visible bra straps. And colors. And random sheers. And bridesmaid-y heels. Christina Aguilera is here giving us all of it in one red carpet photo.

Claire Danes

Romeo + Juliet was a huge huge hit (and a star-making performance) for Claire Danes, which is why I am quite sad that she came to the premiere in those uniquely '90s spiky hair ponytails pointing in every direction, plus a whole lot of satin.

Alicia Silverstone

I mean, I get it: The Clueless Malibu premiere taking place on the beach is very thematic branding for the film. But why did the people involved have Alicia Silverstone walk on the beach in open-toed heels? Isn't the sand just going to get into her shoes??

George Clooney

Did you know that George Clooney used to have long, rich, luxurious hair? Because I certainly did not. (This is in promotion of the film Red Surf, so I get the surfer aesthetic is strong here, but this could not be farther away from his very sexy doctor vibes he would debut a few years later.)

The Spice Girls

We all know and love the Spice Girls for the unique fashion they blessed upon the world. This was at the 1997 MTV Europe Music Awards and helped introduce the girl group to a larger audience, so I just wanted to take a moment and really let Scary Spice's outfit sink in. We used to wear this!!

Sharon Stone

Sharon Stone, popularizer of high-low fashion, incredibly chic actor and star, one time went to the MTV Movie Awards with feathers on her head. Sharon, I am sorry to tell you that the shades are not making this look cooler (although taking the gloves off might have helped? I don't know.)

Mariah Carey

I just really enjoy that the caption on this photo reads, "Mariah Carey takes a break for her favorite snack at McDonald's," because this is clearly an ad (Carey has continued to work with the brand!) and I appreciate her faux "Here I am, just delicately eating a fry!" face.

Tom Cruise and Nicole Kidman

Something about this photo—the matching shirts, perhaps, or Nicole's posing, plus the fact that this is just listed as "a sighting" of the married-at-the-time couple but looks...highly staged—just feels very peak '90s to me in a way I hope we've moved past.

Melissa Joan Hart

If you're going to watch the 20th anniversary of Grease, you obviously go wearing Grease cosplay! (Red carpets: way more casual than they are now!) These days, I feel like a celebrity costume would take months to prep, but Melissa Joan Hart clearly just threw on some related clothes and called it a day.

Ryan Reynolds

Ryan Reynolds was not always the hot dad/superhero/owner of a Welsh soccer team that he is today. Back in the day, he was just a guy in a soul patch showing up to a movie premiere (Election, in case you're curious) in the most '90s bro outfit of all time.

Lil' Kim

When I say painful, I literally mean it in this case. Lil' Kim (who was doing over-the-top red carpet dressing before everyone else) is crouching to set down a Soul Train Music Award, while also endeavoring not to have a wardrobe malfunction and keeping her pearl mesh outfit in place. None of this looks comfortable??

Jason Bateman

Bawww, little Jason Bateman with a fanny pack at the Los Angeles International Airport is the baby-faced throwback I didn't know I needed! Airport style has improved since the '90s; This is a good reminder that a lot of stars at the time just didn't have stylists—and we could tell.

David Hasselhoff

I am...mesmerized. Barefoot, peak-Baywatch, mullet-y David Hasselhoff. A dog with his exact same haircut. Both of them staring soulfully into my eyes. Is this for an event, an ad for perfume, or something that Hasselhoff liked to do on his days off?

Jean-Claude Van Damme

There is something so deeply soothing about a be-suited, mulleted Jean-Claude Van Damme giving us a side kick in front of a pool. (He's promoting the film The Quest at Cannes, but in my mind he just gathered a bunch of photographers in front of a pool to kick for them.)

Jennifer Lopez

The appeal of the "just out of the water" photoshoot is the wet, warm, sun-kissed vibes you're supposed to channel. J. Lo just looks damp here, poor thing (and the other photos, including one of her on a wooden couch, make me convinced this was the most uncomfortable photoshoot of all time).

Kevin Costner

Lol, remember the days when we had people pose for "casual" shots and they just ended up looking incredibly uncomfortable? I give you a young Kevin Costner hanging off a random bannister in perhaps the best example of what I'm talking about.

Claire Danes

I can see it now: "Claire, I'm gonna need you to get up on that jungle gym—don't ask questions, it's my artistic vision—and hang upside down and pretend like you're having fun. Now kick the camera. Kick it!!" Casual photoshoots, especially for teens (Danes was 15), are really something special.

Sarah Michelle Gellar

Not only does this look impossibly uncomfortable, but a young Sarah Michelle Gellar here is also wearing, as far as I can tell, an overalls vest? (And also pulling this horrible pose off as well as anyone possibly can!) Imagine if you asked literally anyone to do this today.

Mark-Paul Gosselaar

This is Mark-Paul Gosselaar in the middle of his Saved by the Bell fame, so of course you should take one of our nation's hottest teen actors, stick him in a Canadian tuxedo and matching glasses, and have him slouch at the camera with an expression that's just as confused as ours.

Mary Beth Evans as Dr. Kayla Brady Johnson, Stephen Nichols as Steve "Patch" Johnson

I fully recognize that this is a still from Days of Our Lives and not, like, a photo of an actual wedding, but I present this here as a testament to how wild that show really was in the '90s (remember how Patch "died" in a boating accident planned by an evil oil baron??).

Robert Downey Jr.

Robert Downey Jr., who would go on to be a stylish and successful film actor, here presents us with a silver blazer and matching pants, purple shades, sheer mesh top, and general "I'm so cool" attitude. Shocking no one, these trends have not resurfaced.

Andre Agassi

The Canadian tuxedo, the long hair, the bangs, the tie, the pamphlet sticking haphazardly out of his pocket: Andre Agassi is all the '90s dad cliches in one outfit! '90s red carpets: more casual than you remembered. No one had a stylist!

Justin Timberlake

For our frosted tips heyday, no one did it "better" than Justin Timberlake. Perhaps it's the ultra-curly hair, oversized blazer, matching shades, or diamond earring, but Timberlake had a few steps to go before his ultimate destination of teen heartthrob sensation.

Beyoncé and Kelly Rowland

Destiny's Child really leaned in on the matching outfits, but this one is...a lot to unpack. I really wish we had betters photos of the magnificence. Denim two pieces with strategic cutouts on top? Random holes in your pants?? Tell me more, Beyoncé and Kelly!

Bill Gates

I suspect this is just a random press photo, but having billionaire-to-be Bill Gates pose "casually" on what looks to be an ironing board, and just have a sheet draped haphazardly in the background, feels about right for what computers were in the '90s.

Cameron Diaz...and Gameboy

Oh, nothing. Just Cameron Diaz casually stroking a Gameboy (that's not how you're supposed to play it!). A photoshoot, yes, and an ad, probably, but to me there's nothing more '90s than national treasure Cameron Diaz being forced to stroke a handheld game console and look enthused.