Rarely Seen Photos That Reveal A Different Side To The 90s

By Sophia Maddox | February 5, 2024

Madonna, Sting, and Tupac Shakur, hanging out together in 1994

The following unseen photos from the 90s are definitely too hot for some viewers. Are they for mature audiences only? We'll leave that decision up to you…

The final decade of the millennium was an era of change. Generation X had taken the societal reigns from the Baby Boomers and letting their hair down. Fashion was taking a turn for the flannel, and young people were beginning to look for new ways to have a good time.

These snapshots of the 90s show that the decade was full of a kaleidoscopic mix of culture, fashion, and music that made it an unforgettable era to live in - when Anna Nicole Smith was a legitimate celebrity and when Johnny Depp was still considered an independent film star.

It's important to use these pictures from the 90s to take your preconceived notions of the decade and turn them on their head. That's the coolest part about taking a deep dive into the past… you never know what you'll find on the other side.

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source: reddit

Prior to the ‘90s the music world was extremely segmented. Rock artists hung with rock artists, pop artists weren’t thought of as cool, and rappers were in their own world.

By the last decade of the millennium pop culture was a place where everyone mixed and enjoyed one another’s company. How else do you explain Sting hanging out with Madonna and gangster rapper Tupac?

Madonna and Tupac dated briefly in the early ‘90s, maintaining a friendship until he was gunned down one year after this photo was taken. The two were together in 1994 when Madonna appeared on David Letterman’s show absolutely went wild. Look it up on YouTube She claimed that Shakur had riled her up before the interview, thus her colorful language.

A breathtaking photo of Angelina Jolie taken in 1998.

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source: People

In the early ‘90s Angelina Jolie was essentially a cult star. A beautiful young actress with enticing eyes and a million dollar smile, she played tough chicks in b-movies and a hot hacker in her first blockbuster role, but it was her starring role in Gia that earned her a Golden Globe and established her as a star to watch.

Following her win for Gia she was profiled in People Magazine and photographed by the great Greg Holzer. He later said that during the shoot Angelina was captivating and exciting, that she was down for anything:

Angelina arrived with no makeup, no publicist, and no entourage, and settled in with my glam squad. She was incredible in front of the camera. We did the safer images that the magazine required in the beginning, then ended up shooting for hours more. Inventive, spontaneous, and fearless, she gave 100% to the camera… Angelina was the perfect combination of model and actress: beautiful and very self-aware, yet emotionally rich and expressive. When people ask, ‘What was your favorite shoot?’ I always think of this one.