“I’ll Be Watching”: Aware of the Precarious Nature of His Actions, Dennis Rodman Once Swept $150 Million Music Legend Off His Feet

Published 08/16/2023, 7:50 AM EDT

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In a moment that would redefine the norms of self-expression, Dennis Rodman took a daring step towards embracing his true self in 1996. This captivating episode from his memoir sheds light on a pivotal turning point in his life. The scene unfolds with Rodman dressed in an eye-catching outfit, prepared for a life-altering event. As he descends in an elevator, on his way to a horse-drawn carriage accompanied by eight elegantly dressed grooms-women, he ran into a $150 million worth rockstar.

The interaction between the two inspired the Worm to stay true to his audacious ways.

Dennis Rodman leaped into the unknown in 1996


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Promoting his book Bad As I Wanna Be, Rodman decided to up the ante in the way only he can. Pulling up the event in a horse-drawn carriage, the five-time champion was donning a wedding dress. He would later reveal how a rock icon supported his transformational moment.

As Dennis left his hotel for the event, fully clad in a white dress and makeup, he was joined in the elevator by rockstar Steven Tyler.


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“Dennis?” Steven Tyler uttered in a hushed tone. “Steven,” Dennis responded, their tones synchronizing. “You go, man,” Steven encouraged. “I’ll be watching.”

Rodman often reflects on his journey of public eccentricity – from rainbow hair and tattoos in San Antonio to flamboyant makeup and boas in Chicago. But in 1996 he knew he was stepping onto the world stage in an unprecedented manner,

However, what he was about to embrace went beyond mere eccentricity; it was a daring leap into uncharted territory. To him, this wasn’t just about having fun; it was about challenging societal boundaries and norms. This bold move not only made waves but also garnered support from Steven Tyler, the lead singer of Aerosmith and a four-time Grammy Award winner.

His embrace of femininity and flamboyance marked Rodman as a trendsetter who was, perhaps, ahead of his time.

The Worm challenged offenses and norms


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Dennis Rodman, the renowned Chicago Bulls legend, pushed boundaries, both on and off the court. One of the most notable instances of his daring fashion choices was his embrace of cross-dressing.

Doing it so early on marked a significant milestone. It was a profound departure from the traditional male athlete image, delving into what he termed “homo-world.”

The inherent risk in this endeavor loomed large, as no active male athlete in any major sport had ever ventured into such uncharted waters. There was a time when Rodman thought that he’d go to prison.


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In a career marked by head-turning moments, one stands out prominently: Dennis Rodman’s decision to wear a wedding dress as a publicity stunt for his book, Bad As I Wanna Be.

Watch the story: I Can’t Wreck My Brain”: 164 Days After Winning the President’s Award, 41 YO Dwyane Wade Reveals His Mantra To Distance Naysayers


Written by:

Nischal Bahuguna


One take at a time

Nischal Bahuguna is an NBA author at EssentiallySports, with a deep passion for sports and writing. He is an NBA enthusiast and a seasoned basketball player. With over two years of professional writing experience, Nischal seamlessly blends his interests and skills to excel in his craft.
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Edited by:

Aakash Nair