Slate's Yes-Man-in-Chief

Never let it be said that Jacob Weisberg doesn't have a sense of humor. Weisberg, the chairman and editor-in-chief of The Washington Post.Newsweek Interactive's Slate Group and co-author of former Treasury Secretary Robert E. Rubin's memoir, In An Uncertain World, is currently appearing on SlateV in a funny, useful video about office yes men, those boss-buttering lickspittles who seem to lurk in every office.

The video is the latest installment of 'Hey, Penny' the workplace advice column on Slate's business-focused brother site, The Big Money. In his wordless, Buster Keaton-ish turn, Weisberg acts like a stereotypical brown-noser, offering a powerful white guy CEO-type cookies, eagerly popping a thumbs up or throwing a thumbs down to mirror his boss' moods, and generally acting like a total jerk. Penny, the site's Daria-ish advice columnist (played by writer Jennifer Predige), offers some pretty good advice for neutralizing these solicitous suck-ups—maybe even if they're you're boss, like Weisberg.

At least Weisberg appears to be in on the joke. In June, The New York Times' managing editor Bill Keller (among others) appeared in a Daily Show with Jon Stewart segment that made him look utterly foolish as he attempted to explain to correspondent Jason Jones why his paper should survive. The segment, almost predictably, was called End Times.

Keller received so much criticism for his apparently clueless appearance in the segment, he felt compelled to tell Time Magazine, "[T]hat's the last time I try to be a good sport. Even my wife told me that I looked faintly ridiculous, and she was trying to make me feel better."

Ouch. But he managed to follow that with a little jape of his own: "Among the people who would miss us most would be the wise-guy pundits and scriptwriters for satirical TV shows, because they riff on the news we produce."

Sure, that’s not much of a joke, but it's pretty funny.