With all games on hiatus, ESPN’s fascinating 10 part documentary The Last Dance has captured the imagination of a sports-starved nation and spurred a wave of nostalgia for the Chicago Bulls dynasty of the 1990s.

Naturally, because it combines 90s basketball and a functioning TV camera, that means Dennis Rodman is going to show up. A lot. Last week’s Episode 3 was devoted largely to Rodman’s triumphant but tumultuous tenure in Chicago, covering topics like his 48 hour Las Vegas “vacation” that appeared to be inspired by the training regimen of Nicholas Cage.

It’s hard to overstate how much Rodman fascinated the entire country during that time, a fascination he was eager to feed. As a recently rediscovered mid-90s appearance on Oprah underscores, one of the sources of that fascination was endless speculation about Rodman’s sexuality.

The interview ages about as well as the style choices of the “Smells Like Teen Spirit” extra over Oprah’s shoulder. Rather than let Rodman define who he is on his own terms, Winfrey repeatedly tries to pry it out of him with a rapid fire barrage of “So… are you bisexual?” and “If you were gay, I believe you would tell me.” To add an extra touch of cringe, someone in the crowd applauds Rodman’s declaration that he’s not bi.

As someone who went to high school in the Chicago suburbs in the 90s and was heavily closeted during that same time, let’s just say every bit of this clip strikes me as very familiar.

Rodman was one of the most prominent athletes of that era to publicly turn the image of the hyper-masculine athlete on its head, although it was always cause for debate whether he was being authentically himself or just seeking publicity. As a 1996 San Francisco Chronicle article noted, Rodman often liked to buck conventions of the time by making appearances in make-up, painted nails, and a shirt reading “I don’t mind straight people as long as they act gay in public.”

He also admitted, “I like bringing out the feminine side of Dennis Rodman… I can’t say I haven’t experimented with other men but I guess it depends on what you mean by experimenting.”

But at the same time, Rodman’s most famous incident of gender nonconformity was wearing a wedding dress to a book signing in New York as a publicity stunt to plug his autobiography. This was an instance of him living his truth. But that truth was “I’ll wear anything to get you to spend $24.95.”

Top this, Kurt Vonnegut!

Still, stunt or not, Rodman did broaden the public consciousness of how a male athlete could define his identity. And he could also be very public about being an ally at a time when such a sentiment wasn’t nearly as widespread as it is today—in sports or society in general.

During the 1995 NBA Playoffs when he was with the San Antonio Spurs, for example, Rodman took the court with this new hairstyle:

Suffice it to say, it’s hard to think of another NBA player at the time who was willing to so prominently display the AIDS ribbon on his person. Nor were there many players who were willing to admit, “I felt like calling attention to AIDS” in response. Especially less than four years after Magic Johnson’s revelation that he had contracted HIV and all the rumors that followed in its wake.

So while Rodman’s motives for his actions were often self-centered, the fact of the matter is that he did redefine the image of how a superstar athlete could break through the barriers of masculine conformity. He also helped ignite a conversation about sexuality in sports and even today, he still manages to be on the right side of history on this issue.

As his conversation with Oprah demonstrates, that was a much more daunting place to be in the 1990s.