The passing of a gay icon like George Michael, way before his time, will continue to hit hard in the Castro and around the Bay Area for days to come — a devastating blow in this year's growing list of obituaries, which includes gay icons Prince and David Bowie. And despite Sunday night being a pretty quiet one around the Castro neighborhood, CBS 5 made a beeline for the bars and found "Last Christmas" blaring at Badlands, and other bars marking Michael's passing using his incredible catalog of pop hits.

Unlike Bowie and Prince, George Michael was in fact gay, and even paid a price in his career when he became publicly so. But long before the "lewd act" he was busted for by an undercover cop in LA — in a sting that would probably be called homophobic today — gay men and boys recognized him as one of their own. As one Castro resident told CBS's Joe Vasquez, "For [performers] who were gay, they didn't have to say they were gay for us to know that we connected with them on a different level. George Michael was that guy. We all knew that he was... cool. And we could relate to him."

Missing from some of the narratives memorializing Michael, though, is the way in which he traded his ongoing pop stardom and privacy in order to fully embrace his accidental and embarrassing coming out, via that 1998 arrest in a public men's room in Will Rogers Memorial Park in Beverly Hills. Rather than apologize or lie low in the wake of that incident, Michael chose to make a music video for his song "Outside" mocking the cops, making light of his arrest, and pointing out the hypocrisy of the fact that straight people don't get targeted for arrest for expressing their sexuality in similar ways. (See the mock straight Euro porn scenario in the opening of the video below.)

The video is a remarkable "fuck you" to the system that arrested him and to societal mores in general — made more remarkable by the fact that the song was written and the video shot within two months of his April 1998 arrest, in June of that year. The song debuted later in the year along with the release of the greatest hits album, Ladies & Gentlemen: The Best of George Michael.

As a friend describes the video on Facebook, "It's unapologetically gay (disco urinals, cop uniforms, locker room cruising). It's empowering. He potentially traded fame and did not give a fuck at [that] point. And yet behind the glitter and thump the lyrics are sad. A lover longs to have a normal relationship, outside. For many years, and still for many around the world, that's not possible [for gay men]."

But while George Michael the star took this embarrassment and made something empowering out of it, there's no doubt that it impacted the breadth of his fan base, not to mention his own already conflicted relationship with fame — and maybe knowing this, his final studio album of original music, Patience, would not be released for another six years, in 2004. The album boasted even more unapologetically gay-inflected dance songs like "Flawless" and "Freeek!," and it was met with fairly tepid record sales. Patience sold 4 million copies worldwide, with only 381,000 in the US. Compare that with his poorly reviewed previous studio album in 1996, Older, which sold 8 million copies, over a million of those in the US (which at the time was considered kind of a flop).

"Flawless" has a similarly empowering message to "Outside," telling everyone "you're beautiful" and "I think you'll make it in the city... and you'll learn that you're more than just some fucked up piece of ass." And the video features a diverse cast of characters and dancers, including a drag queen in lingerie, all turning one hotel room into their dance floor, with the singer himself smiling in the middle of the party and taking it all in.

Patience also included the very personal ballad "My Mother Had a Brother," which is about Michael's closeted gay uncle who took his own life the day that Michael was born. In the song, when he asks his mother why his uncle died, she says, "He couldn't wait for the things that I've seen. She said he wasn't strong enough he never dared to dream a life like mine."

In a 2005 interview with the UK Guardian, Michael described going through 12 years of depression and heavy cannabis use, which he says helped him write the album Older, and which he seemed to blame for his overall lack of creative output during the previous decade.

He also explained that he had initially thought about coming out as gay when he was 19, but he was unsure of his own sexuality and was advised not to, for his career, and then later he says he avoided coming out because he didn't want his mother to live in fear that he would contract AIDS. Later, though, he would become one of the most outspoken gay figures in pop music's history, opening up to the media about his open relationship with boyfriend Kenny Goss — something he alludes to in the song "Amazing," singing "You tried to save me from myself / Said 'darling, kiss as many as you want! / My love's still available / and I know you're insatiable."

As he told the Guardian, "You only have to turn on the television to see the whole of British society being comforted by gay men who are so clearly gay and so obviously sexually unthreatening. Gay people in the media are doing what makes straight people comfortable, and automatically my response to that is to say 'I’m a dirty filthy fucker and if you can’t deal with it, you can’t deal with it.'"

And therein lies his connection to the unapologetic San Francisco gay community, and the philosophy of not only being out, but being photographed with coworkers in your leather at Folsom Street Fair, and not giving a damn.

Sadly, with his public arrests (including one for driving under the influence of marijuana in 2010), and compromised health at a relatively young age, George Michael will not get to be exceptional in his longevity as a gay icon. Not unlike Judy Garland before him, an icon whom gay men adored in large part because of her flaws and addictions, George Michael passes on well before fading into his golden years. He was a first of his kind major pop star to be both an icon and an out gay men, and to demand that the media and public accept him as both.

In the spirit of his newfound freedom to say whatever he wanted in later life, and to still embrace his serious love of pop music, below you can see George Michael in James Cordon's first ever "Carpool Karaoke" routine, for Comic Relief 2011 in the UK.