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

By Sophia Maddox | January 22, 2024

Dennis Rodman gives David Letterman matching green hair on the Late Show, August 1996

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: CBS

After Dennis Rodman joined the Chicago Bulls at the start of the 95 - 96 season he was no longer just the bad boy from the Pistons but a member of a full blown championship team.

Rodman started appearing on Letterman’s show in video segments whenever the smarmy host was in town. In 1996 Rodman appeared as a guest on the actual show and brought along some spray on hair dye that he used to color Letterman’s fairly boring hair-do.

This was one of the many segments during the ‘90s on Letterman’s show that would become polarizing, along with Drew Barrymore’s birthday dance and Madonna’s many many f-bombs. 

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.