Just because tonight is the last time he’ll host The Tonight Show after a 17-year-run doesn’t mean Jay Leno is going anywhere. He’ll be popping up five nights a week at 10pm on NBC this fall! So there’s no real loss of Leno, just a time change. But will a new time slot change Leno’s lowest common denominator punchlines? Probably not. But will it make Leno more gay-friendly?

That’s a more difficult question.

Leno has a not-so-great history with the gays. Like any comedian, Leno steps into controversial territory now and then for the sake of a laugh. This is the nature of the humor business, and sometimes it can go over well. Other times, not.

Sure, you’ll rarely find a white comedian who broaches racial jokes, but sometimes they do, and sometimes they’re funny! And it’s not like straight comedians can’t make gay jokes. They can.

Craig Kilborn did it: “Governor Schwarzenegger has come out against gay marriage and then he went back to slathering body oil all over his muscles in front of other guys.”

Craig Ferguson, too: “Republicans say they plan to press for a constitution amendment to ban gay marriage. Because the founding fathers intended gay sex to be very casual. They didn’t want it to be married.” And: “Maine legalized gay marriage today. Maine became comfortable with the idea after years of touching Canada.”

But how come whenever Leno approaches Gaytown, we cringe?

The late night host’s most recent gay joke scandal involved Ryan Phillippe, who Leno asked the Stop-Loss star to make his best gay face for the camera. “Can you give me your gayest look? Say that camera is Billy Bob… Billy Bob has just ridden in shirtless from Wyoming.” (Smartly, Phillippe refused to play along.)

Leno ended up apologizing for the incident, but only after folks like Avenue Q writer Jeff Whitty (seen in the interview clip above) publicly complained about the incident.

Of course, this isn’t Leno’s first time making gays the butt of a joke. He’s turned to Brokeback Mountain (“Both Crash and Brokeback Mountain had similar themes: Whether you’re a driver in L.A. or a cowboy in Montana, keep checking your rearview mirror … you don’t know who’s coming up behind you.”) and all but painted Hillary Clinton as a bull dyke during the presidential campaign. (Conan O’Brien has entered this territory, too.)

The problem with Leno, then, isn’t that he makes gay jokes. It’s that he does so at the expense of gay people. His comedy doesn’t make us feel included, but hijacked. Maybe this has something to do with Leno’s target audience (middle-aged Middle America or something), so you know he’s kowtowing to a demographic that might have a gay friend, but finds ruthless gay humor HYS-TER-I-CAL. But how come other late night comedians manage to include our kind in their punchlines in a way that even we start laughing?

What will differ with Leno’s move to 10pm isn’t quite clear, but we expect the more risque humor will be toned down for the earlier hour. Whether that includes his terribly unfunny attempt at gay humor is anyone’s guess.

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