A Look Back at Jon Stewart’s Greatest Gay Moments

There’s a whole lotta gay going on in the brand-spanking-new archive of The Daily Show video clips launched last week by Comedy Central. Ever since 1999, when a relatively unknown political humorist named Jon Stewart took over as anchor and made “fake news” a household word, the anti-gay elements of society have been one of the main targets of his increasingly impassioned, brilliantly funny fake newscasts.So let’s check out the best of the best by looking at the highlights of the last eight years, stopping along the way to note a time or two The Daily Show really blew it (and not in a good way).

It does bear mentioning that there are plenty of queer comics doing pro-gay political humor. And Stewart isn’t even the only straight comic who supports gay rights. Kathy Griffin, Roseanne Barr, and many others have championed our issues and earned large queer followings. Stewart isn’t even the only straight male political comic with his own TV show who supports LBGT equality; so does, for example, Bill Maher.

What sets Stewart apart, aside from his tremendous mainstream popularity, is that his humor conveys a deeply-rooted sense of personal outrage at anti-gay policies, laws, and attitudes. He doesn’t, like Maher, support gay civil rights as part of an overall libertarian or progressive political ideology, but because, as he told conservative pundit Bill Bennett in what may be the greatest interview of Stewart’s career, gay equality is part of “the natural progression of the human condition” because “every gay person [is] someone’s son or daughter.” And in Stewart’s mind, apparently, you just don’t treat your kids like that.

It also has to be said, no matter how much it hurts, that Stewart isn’t perfect. Oh, his sense of humor rarely misses, and his hair actually really may be perfect. But when it comes to gay political humor, sometimes The Daily Show gets it wrong – hello, Stephen Colbert gay-baiting the inventor of “Gaydar,” a little electronic device that will vibrate whenever anyone else in close proximity has the same device.

It’s also true that The Daily Show and its spin-off, The Colbert Report, haven’t been making a lot of friends in the MySpace generation or the blogosphere lately. That’s because those buzz-killers at Comedy Central have been rampaging around YouTube and other video-sharing sites for months now, getting those shows’ clips yanked as fast as they went up. The reason is now clear: They’ve been building their own little Daily Show video universe, where every single clip of every segment of the show since the day Stewart joined its cast in 1999 can be viewed and embedded. The Colbert Report will be getting the same treatment soon.

The Daily Show site launched in mid-October with the butt-covering word “Beta” scrawled under the logo, probably to account for the fact that a lot of times, the videos just won’t play. Still, those seeking the gay can lose many, many hours in The Daily Show vaults, reliving past moments of queer glory and discovering many others previously unknown. After all, no fan, however obsessed, can ever really have seen every single episode – until now.

Pure Gold: The best of the best


June 5, 2006
Bill Bennett on Gay Marriage

This is the one where Stewart broke all the rules. The guy renowned for being a softball interviewer, who bonded with Rick Santorum over ice cream, who couldn’t even bring himself to put Lynn Cheney on the run, threw right wing values guru Bill Bennett to the sharks, and laughed at the blood on the water.

Stewart challenged Bennett by asking, Isn’t Vice President Cheney the perfect example of a socially conservative political candidate? Or in his exact words: “Dick Cheney: Conservative. Draconian. Drinks the blood of puppies.”

Bennett reluctantly conceded that to be the case, knowing what was coming. And yet, Stewart pressed, he doesn’t oppose same sex marriage. Why is that?

Bennett said it was because Cheney’s daughter is a lesbian, as if that made Cheney’s views on the issue less, rather than more, informed and relevant.

“Isn’t every gay person someone’s son or daughter?” prodded Stewart.

Bennett agreed, but didn’t seem to think that was the point. After fumbling for a while with some kind of rambling values discourse, Bennett stopped. “This debate is over, Jon.”

“Yeah. You lost.”

Said Bennett, “Absolutely. Gay marriage is coming…because the courts have done it…”

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