40 Vintage Photos of Celebs That Are Too Cool for School

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Are you ready to see the coolest photos of your favorite celebs, pictures that are totally rare and until now not seen by many?

Well, it’s happening, so buckle up.

David Bowie

Here’s the king of cool (that’s his nickname, right? Well it is now!) on October 20, 1977, at the Dorchester Hotel in London.

Axl Rose

I don’t think it can be overstated how much good Axl Rose, Guns ‘n’ Roses frontman, did for gingers everywhere.

Winona Ryder

Winona Ryder was photographed here in 1989. She is just the coolest, and I am so very glad she’s made a comeback.

Jason Momoa

He looks a little different these days, but yes, that is Jason Momoa way back in 1999 filming Baywatch in Hawaii. Talk about a glow-up.

Bruce Springsteen

Here’s The Boss in 1978. For a pretty small dude, he sure can bring the house down in any stadium anywhere in the world.

Princess Diana and Drew Barrymore

That right there, folks, is Princess Diana meeting Drew Barrymore and holding a stuffed E.T. doll. And yeah, that’s Steven Spielberg in the background.

Natalie Portman and David Spade

Is this an odd pairing or what? And have you ever seen a bigger suit? This was taken at the MTV Movie Awards in 1996 and we’re pretty sure Natalie Portman blocked this from her memory.


Cher invented the phrase “long hair don’t care.” OK, she didn’t, but here she is looking fly as hell on The Sonny and Cher Comedy Hour in 1974.

Gwen Stefani

No Doubt was supposed to open for Bush at the Pond in Anaheim, and she forgot something important at home, so she ran to get it in her curlers, and this photo was taken!

Halle Berry

This woman literally has not aged in decades. Here she is at the NAACP Image Awards on January 11, 1992, in Los Angeles, CA.

Prince William

Look at this adorable kid! He looks quite different now. And oh man did he used to look just like his mom!

Leonardo DiCaprio

Yup. That right there is baby Leonardo DiCaprio being held up by his cool parents, Irmelin and George.

Marilyn Monroe

This is a candid photo of Marilyn Monroe, makeup-less and in the pool having a great time! You never really see her being totally silly like this.

Gwyneth Paltrow and Brad Pitt

Wow. It doesn’t get more ’90s than this, folks. The tiny, transparent sunglasses and their matching blond shags? It’s too much to handle.

Drew Barrymore

Drew Barrymore has been in the public eye since she was a tiny little toddler. She definitely had her…um…phases, but she’s currently one of the coolest people in Hollywood, hands down.

Amy Winehouse

Amy Winehouse was a force to be reckoned with. Her albums are still some of the greatest of all time, and she is dearly missed by so many.

Will Smith

This photo is straight from the series wrap party for The Fresh Prince of Bel-Air. Who knew Will Smith would become the superstar he is today?

Marlon Brando

Hold on. I have to catch my breath after looking at this photo. Whew.

Julia Roberts

Julia Roberts out here looking like the Hamburglar at the 1993 NATO/ShoWest Convention. That’s a lot of stripes, girl.

Johnny Depp

Johnny Depp used to be one of the hottest celebs around. His hair was absolutely iconic.

Janis Joplin

Here’s Janis Joplin backstage at Winterland in 1968, a total icon with her bottle of Southern Comfort.

Tyra Banks

Tyra Banks is photographed during a fashion show in 1994. She honestly looks like a real-life Barbie here, which explains why she was so perfect in Life-Size.

Angelina Jolie

Angelina Jolie has reached such celebrity status that she’s pretty much otherworldly at this point. But I did see her in a movie theater once taking her kids to see the new Jumanji, and she’s a person, just like us, only with security staff.

Prince Charles, Jennifer Aniston, Stephen Fry, and Ginger Spice

This might be the most ’90s picture on the list. Just look at it!

Joan Jett

Joan Jett was hanging out in Santa Monica when this photo was snapped in 1977. She’s pretty much the coolest person alive.

Mick Jagger

This portrait of the Rolling Stones frontman was taken in Paris in 1971 by Jean-Marie PĂ©rier. The man is a living legend.

Ryan Phillippe

David LaChapelle took this photo of Ryan Phillippe. This is peak Cruel Intentions era, and let me just say, that mesh shirt is really something.

Alicia Silverstone

Alicia Silverstone wasn’t all silly and bubble like Cher in Clueless. She was ultra-serious when she was being photographed with her hair hanging weirdly over her neck in 1995.


1986 Madonna was full of religious iconography and also looking like she just got out of the shower. But it’s OK because she can do no wrong.

Jimmy Page

This Led Zeppelin guitarist looks like every hipster in Brooklyn who brews their own beer.

George Harrison

George Harrison might be the coolest Beatle. There. I said it.

Audrey Hepburn

Audrey Hepburn is pictured here in the gorgeous wedding gown from the movie Funny Face. The epitome of beauty!

Keanu Reeves

Annie Leibovitz took this badass photo of Keanu Reeves for Vanity Fair in August 1995. Those leather pants. I can’t. He also doesn’t ever age.

Heath Ledger

Heath Ledger was a true gift to the acting world, and it’s a terrible tragedy that we lost him. Luckily, his work lives on.

Victoria Beckham

Back then, this fashion icon was known as Posh Spice. She was a leader and a trendsetter and honestly, that hasn’t changed as the years have passed.

Mariah Carey

Mariah Carey wearing sunglasses and eating McDonald’s in Times Square in 1999 is a big mood right now.

Matthew Perry, David Schwimmer, and Matt LeBlanc

The men of Friends, everyone! Man, they had some good hair back then.

Shelley Duvall

Shelley Duvall is an absolute icon, and this photo proves it. Her performance in The Shining is simply incredible.

Christie Turlington, Naomi Campbell, and Kate Moss

This photo was taken at the Met Gala in 1995. This right here is supermodel royalty. It doesn’t get much more famous or iconic than this.

Michael Jackson

We end with Michael Jackson, smiling in his iconic red leather jacket. The celebrity power is too great with this one. Share this with the celebrity-obsessed person in your life!