A person with long hair and sideburns holds a microphone and gestures with one hand while looking to the side in a black and white indoor setting.
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Some Hollywood stars knew how to take the riches they earned through their peaks and valleys and turn them into unimaginably grand scenery. It’s fun to pause and acknowledge the imagery that came with the riches Hollywood stars accumulated. These snapshots certainly provide their own entertaining carousel of the times had.

1. Elton John

A person wearing a sparkly cowboy hat decorated with colorful stars is singing or speaking into a microphone on stage with a red curtain background.
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Elton John went and dressed up like Mozart during his 1986 tour with the Melbourne Symphony Orchestra. Clearly, donning a “normal” tux wasn’t the grand plan at hand.

2. Prince

A musician in a ruffled white shirt and shiny purple jacket performs energetically on stage, holding a guitar and gesturing with one hand near his face in front of a microphone.
Michael Ochs Archives / Getty Images

Prince went and opened Paisley Park in 1987. Then proceeded a tremendous sprawling creative compound with recording studios and a Hollywood-sized soundstage that was built around his work.

3. Michael Jackson

A singer with curly black hair in a red outfit passionately performs on stage, holding a microphone and raising one hand in front of their face against a dark background.
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Michael Jackson bought the ranch that then became Neverland in 1988, and in the process turned it into a private world with amusement rides, to boot. And, get this, a theater, and a zoo.

4. Liberace

A pianist in a sparkling black jacket smiles while playing a grand piano on a dimly lit stage with a candelabra and musicians in the background.
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Liberace could go ahead and arrive in an actual crystal-covered car, and then proceed to emerge from an enormous Fabergé-style egg, and in a pink feather cape. Even his piano had a whole glitter getup.

5. Grace Jones

A person with dramatic makeup, wearing a brown and maroon hooded outfit, smiles while sitting on a light patterned sofa with a cream-colored curtain in the background.
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Grace Jones moved on through the decade as both a nightclub fixture and a performance wonder. Bringing her theatrical cabaret to Paris’s Le Palace in 1984.

6. Freddie Mercury

A man in a white tank top sings passionately into a microphone and plays the piano on stage under dramatic lighting.
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On his 39th birthday, in Munich, was a black-and-white drag ball that was so memorable that photographs and pieces of his outfit then later became auction lots.

7. Rick James

Two people in formal attire, facing each other and smiling, are in the foreground at an event. A man in a tuxedo stands in the background. The lighting is dim and the mood appears festive.
Michael Ochs Archives / Getty Images

Rick James had much success with “Super Freak” and that right there fueled some lavish tours and extravagant parties in the process. His own biography details him partying on par with something like a Roman emperor.

8. Ozzy Osbourne

A person with long hair and sideburns holds a microphone and gestures with one hand while looking to the side in a black and white indoor setting.
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Ozzy Osbourne in the early ’80s had plenty of notorious exploits. This included an infamous bat incident at a 1982 concert, and then an arrest after a decision to urinate on the Alamo Cenotaph. The reason why? Who knows? Just an act of chaos by the sound of it.

9. Tommy Lee

Three people in old-fashioned clothing stand on a ship’s deck, looking intensely ahead. A man at the ship’s wheel is behind them. The scene appears dramatic and serious, suggesting an adventure or historical setting.
Michael Ochs Archives / Getty Images

On the 1987-1988 Girls, Girls, Girls tour, his drum kit soared above the stage and then spun him literally head over heels, and mid-solo.

10. David Lee Roth

Two men in black and white, one with short dark hair wearing a collared shirt, the other with long hair, sunglasses, and a flower lei, stand close together and look at the camera.
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Van Halen’s touring rider famously went ahead and banned brown M&M’s backstage. Roth would then later say the odd demand helped reveal whether or not venues had taken the time to read the band’s extensive technical requirements.

11. Axl Rose

Smiling person with long hair and tattoos on their arm sits in the open door of a blue and white vehicle, wearing a sleeveless shirt.
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As the Guns N’Roses fame sped toward the ceiling, Rose then told a 1989 stadium crowd the show might be the band’s last performance. What a moment to sit with, huh?

12. Cher

Two people with big, curly hair stand close together, smiling. The person on the left has dark curly hair and purple eye makeup; the person on the right has lighter, wavy hair and is grinning. An old photo is visible in the background.
Vinnie Zuffante / Getty Images

Cher arrived at the 1986 Oscars in a Bob Mackie creation that was topped off with a gigantic black feather headdress. This in effect turned a simple red-carpet appearance into a show entirely of its own.

13. Jack Nicholson

A close-up of a man with short hair and a serious expression, looking to his left. He is wearing a dark jacket and the background is out of focus.
20th Century Fox / Getty Images

Jack Nicholson’s Hollywood Hills home was infamous for celebrity-saturated parties, and gave him an offscreen reputation nearly as big as his film career.

14. Mike Tyson

A man in a white jacket sits at a press conference table, holding a red rose near a microphone, with a towel draped around his neck and a branded backdrop behind him.
Vinnie Zuffante / Getty Images

Mike Tyson became a heavyweight champion. What an achievement in its own right. My goodness. Following the death of his manager in 1988, Don King then loaned Tyson $183,500 for an ivory Rolls-Royce.

15. Madonna

A singer with short, curly blond hair performs on stage wearing a layered red dress, holding a microphone and gesturing with her hand, with a dark background behind her.
Vinnie Zuffante / Getty Images

Her 1985 wedding to Sean Penn transpired in a lovely coastal home while a whopping six press helicopters busily circled around overhead. Privacy and spectacle both, collied in truly spectacular fashion.

16. Joan Collins

A woman in a shiny silver dress smiles at the camera outdoors. She has curly dark hair and wears bold makeup, earrings, and holds a black clutch. Other people are in the background.
Vinnie Zuffante / Getty Images

It was during her Dynasty peak that Collins purchased a mansion, then built a fashion and fragrance empire around her image. Then she would go about the entertaining process in a home fit for Alexis Carrington.

17. Boy George

Person wearing dramatic makeup, a black leather hat with a rhinestone anchor, and a high-collared black coat. The background is dimly lit, with other people partially visible.
Vinnie Zuffante / Getty Images

Boy George was a staple at London’s Taboo, where dressing outrageously was pretty much the price of admission. His actual fame took off out of that whole anything-goes club world. And oh boy did it take off.

Meet the Writer

Matt has spent over the last 8 years as both a writer and editor, working in Seattle and Brooklyn, where he is now based. He loves escaping the tirelessly fast pace of the “Mad Apple” that is NYC by taking walks and runs through parks where he’s able to catch up on the latest tea about society from the city’s ever chatty, always hungry, occasionally maniacal, pigeons. They always have a lot to say. When he’s not taking his urban nature strolls, or dutifully combing the deepest rabbit holes of the internet to find the content that’s worth sinking your mind’s teeth into, he’s likely holed up at a dark-lit dive bar with a new book and/or some friends, or just easily he could be on the hunt for the next addition to his steadily growing plant family.