A Look Back at Jon Stewart's Greatest Gay Moments

But he wasn't in that public restroom to have sex, for money or otherwise. No, he just offered the guy twenty dollars for sex because the man was black and “stocky,” and there were other equally black and presumably equally stocky men present, and he was afraid of “becoming a statistic.”

Or as Stewart summarized, "If I was guilty of anything, it was having a twenty dollar bill and a mouth... and loving too much."

Also check out this list of proposed alibis for Allen, in a clip that most definitely is NSFW.

Jul7 17, 2007
You Have No Idea!

One of the things The Daily Show does best is point out the insanity of the political process. Take the Bush administration’s nomination of Kentucky doctor James Holsinger for Surgeon General. Holsinger, of course, is the medical genius who authored "The Pathophysiology of Male Homosexuality," in which he argues that the lack of natural lubrication in gay sex is a clear indication that it’s aberrant, even potentially fatal. He contends that male and female genitalia go together so intrinsically "that it has entered our vocabulary in the form of naming pipe fittings either the male fitting or the female fitting depending upon which one interlocks within the other…. When the complementarity of the sexes is breached, injuries and diseases may occur."

Stewart’s practically bouncing in his chair while he quotes that part about “natural lubrication,” but his re-enactment of the plumbing analogy is probably one of the funniest routines in Daily Show history.

June 22, 2005
Popping a Big Tent

The gay doesn’t begin until about minute four of this six-minute clip, but after that it never lets up. Don’t get me wrong, the first four minutes are really funny even if they are about the hetero porn industry’s support of the Republican Party. But once Stephen Colbert starts having his little porn movie interlude with the pizza delivery guy, well… the scenery changes.

January 25, 2005
Dick Cheney Camera 3

More hypocrisy mining as Wolf Blitzer tries to get Dick Cheney to connect his support of his lesbian daughter and her pregnancy with his party’s anti-gay policies. “How dare you apply my party’s cruel and inhumane family policy’s to my family!” snarks Stewart in his best Cheney-voice (which, by the way, isn’t very good).

Then he asks, “Hey, Mr. Vice-President! Aren’t any other gay people somebody’s kid?”

Eventually Darth Vader shows up. Also, there are more puppy’s blood jokes. Classic.