Deeper and deeper: back in her wilder days, the world's most famous woman gave The Advocate one filthy interview. Today, both the star and the magazine have grown up.

Three pages following Don Shewey's scandalous 1991 sit-down with Madonna, readers of The Advocate were treated to more than 80 pages of raunchy sex. Advertisements for dildos and 1-900 numbers, full-page shots of men grabbing their junk, and classified ads seeking amputees and sock slaves (whatever that means) were smack-dab in the middle of the issue.

In those days, sex saturated The Advocate, but the Madonna issue set something of a benchmark for the magazine. Shewey's interview with the star was undeniably dirty and remarkable as much for the interviewers ballsiness as for his subject's candor.

Shewey: Tell me about Warren Beatty. How big is his dick?

Madonna: I haven't measured it, but it's a perfectly wonderful size.

Shewey: Are you as kinky personally as your image makes you seem?

Madonna: I am aroused by the idea of a woman making love to me while either a man or another woman watches. Is that kinky?

Interspersed among all the randy talk was a serious discussion about the real Madonna and what she stood for.

Shewey: You're still pushing the envelope with [the documentary Truth or Dare].

Madonna: I know that I'm a political person. I'm incensed by the prejudices in the world, and if I can do something with my celebrity to make people see things that ordinarily they may not pay attention to, then I feel responsible to do it.

Naturally, much ink was devoted to Madonna's deep kinship with gay people, queer men in particular.

Madonna: For some reason that's who I have the most camaraderie with. I think, on the one hand, I feel their persecution.... On the other hand, I feel that most gay men are so much more in touch with a certain kind of sensitivity.... To me they're whole human beings.

Shewey: Why is the music industry so homophobic?

Madonna: They're not going to be when I get finished with them.

Reading her words now, the then-32-year-old shows a latent maturity and self-awareness--not to mention clairvoyance.

Shewey: What do you see when you look at the movie Truth or Dare? Describe that woman.

Madonna: I didn't realize how matriarchal I am--how maternal I am.

Enter Madonna, version 2.007: stable, conventional, devoted mother of three, happily married to the same man for almost seven years, superstar (Forbes ranked her the third-most powerful and well-paid celebrity in the world), and devoted humanitarian. She has a serenity and, dare we say, grace that was not apparent 16 years ago.

It seems unimaginable that today's Madonna would ever discuss Guy Ritchie's phallus in print. And it's just as difficult to picture The Advocate carrying ads where people shove phones down their pants. Madge is now sexy rather than smutty (think of her last H&M campaign), and we like to think we are too (note our cover).

Madonna continues to produce great work, piss off the right people, and look damn good doing it. Maybe that's why this magazine remains in awe of her--and why we aspire to follow her lead.

Don Shewey is our current theater critic. To read his entire interview with Madonna, go to Advocate.com.