Y2K Dennis Rodman in Oakley’s

Live sports is currently on a brief hiatus (like everything else in the world right now), but the sports world is in a frenzy thanks to episodes 3 & 4 of The Last Dance. The definitive 10-part docuseries retells the story of the historic Chicago Bulls dynasty that dominated the NBA in the 90s, and has the entire sports world locked into a single storyline like we haven’t seen since before the internet. Every Sunday night, we get two hours of the next chapter in the story, and this past Sunday we got The Dennis Rodman edition. His wild hairstyles and even wilder lifestyle made him more than just a basketball player. He was a cultural icon. A few decades later, a lot of style trends owe a thing or two to Dennis Rodman. His iconic colored hair, painted nails, facial piercings, and eccentric wardrobe said, “I don’t give a fuck” and he lived up to that in every way—from the way he played the game to the way he notoriously tore up Vegas on his legendary “vacations”.

As his fame grew, “Dennis the Menace” found his way into other aspects of culture, letting his eccentric personality lead the way. By the time he was on the Bulls, he was also pro wrestling with Hulk Hogan, starring in his own reality TV show on MTV, and was even winning a few acting awards. He was everywhere. It’s kind of crazy to think he was doing all this, partying, and somehow found a way to start on a team led by a determined Michael Jordan. But Dennis did it. And he did it with style. He was the face of free expression in sport and no matter where he went, he was probably wearing a pair of 90s Oakley’s. Let’s revisit how Dennis worked those Y2K shades into his self-indulgent lifestyle.

“Dennis Rodman” the persona

To promote his ESPN 30-For-30 autobiographical documentary, For Better Or For Worse, Dennis discusses how he created “Dennis Rodman”, the persona. “I didn’t have anybody to help me make ‘Dennis Rodman’. You know, Michael Jordan got Nike, Kobe got Nike—everyone’s got someone to help brand them. I never had anyone. 1983, I branded Dennis Rodman as something different.” After a near-suicide attempt in 1993, Dennis was traded to the Spurs. He quickly dyed his hair a muted bleach blonde and began dating Madonna, who encouraged him to express himself freely. From that point on, Dennis rose to celebrity status and fully embraced the Dennis Rodman persona. He became notorious for his wild lifestyle—partying with celebrities, experimenting with drag, marrying himself, being “more than an athlete” before Lebron re-branded it behind a social activist impetus. And part of being that rockstar was always wearing a pair of sunglasses. In 1994, Oakley released arguably their most iconic silhouette of the 90s, the Oakley Eye Jacket (more on this another time). The sleek design of the minimal wrap-around shades gave a futuristic appeal to Dennis’ look, and whether he was on TV, or sometimes even on the sideline of games, he was in a pair of Oakley Eye Jackets, its successor the Trenchcoats, or the Oakley Straight Jackets.


It’s pretty wild to think they let this man on primetime TV under the name “Rodzilla,” but it’s Dennis Rodman and honestly nothing else would be more appropriate. He was a monster on the boards and his personality off court was equally sublime—the unpredictability at times made you uneasy, but you loved to see it. He carried all of that into the WWE; strutting into the ring, in his tattered nWo shirt and bandana, smoking a cigar, like a real rockstar, and power slammed some of the 90s best into the canvas—including the legendary Hulk Hogan. He would go on to later win the first WWE Celebrity Championship Wrestling tournament. Where success in basketball depends on genuine athletic competition, success in the WWE depends on the strength of the personality. And that was something Dennis Rodman definitely did not lack. Here’s what he was doing the time he ditched an NBA Finals practice:

The WWE just released the “WWE Untold: Rodzilla Runs Wild” documentary on his short wrestling career.

As the story goes, the Bulls had just blown out the Jazz by 42 points in Game 3 of the ’98 Finals and Dennis immediately hopped on a flight from Chicago to Detroit to appear live on Nitro at the Palace of Auburn Hills. Instead of practicing with the team, he was clearly having a better time drinking champagne and smoking cigars on TV with Hulk Hogan, with green hair and a pair of transparent framed Oakley Fives (with the red polarized lenses). What a legend.

He also sold guns

Sort of. Throughout his career, Dennis had a penchant for getting into trouble. Ejections and fines from the league, DUI’s, getting arrested—he really was “Dennis the Menace” on and off the court. So it was only right for him to be that guy in Double Team, his film debut with 90s action star legend Jean-Claude Van Damme. Dennis would actually go on to take home a trio of Golden Raspberry awards for his acting—Worst New Star, Worst Supporting Actor, and Worst Screen Duo (with Van Damme). The movie was a box office flop and currently has an 11% Rotten Tomatoes review. For a guy who wanted to do everything they didn’t want him to do, in many ways, this one feels like a win. In the movie, Dennis is a cyberpunk, motorcycle-riding, gun-toting arms dealer, and was usually sporting custom space age Oakley Zero’s to complete the look. If his performance is forgettable if not at least entertaining, he did so behind some pretty cool iridescent lensed glasses from the future. Oh yeah, and here’s the trailer:

Rodman World Tour

On one Late Night With David Letterman in 1996, David Letterman introduces Dennis as “the most colorful, controversial, and tattooed player in all of basketball.” Dennis comes on the show in his signature green hair and Oakley Eye Jackets to promote his infamous autobiography, Bad As I Wanna Be, as well as his pre-Jackass era reality MTV show The Rodman World Tour, which he described as “you know, doing wild crazy things like I rent G3’s, Rolls Royce’s, and take showers with people.” The people fed off his crazy antics, so he gave everyone a glimpse into his life outside of basketball:

The world saw him for what he was—someone who wasn’t afraid to break the rules. To Dennis, there were no rules. He capped that TV appearance leaving another indelible mark in his legacy, doing something no one in the history of the show had ever done before. He spray painted David Letterman’s hair green on national TV.