This book could easily provide 20 more posts, but it would almost feel like stealing.

Chuck Klosterman’s I Wear the Black Hat collects a dozen or so essays about how we see certain figures in society as good or evil, and how sometimes the differences we feel so deeply aren’t as clear-cut a distinction as we might think. What we forgive in one person, we villify in someone else. Or the ways and reasons we remember some of our heroes ignore what other figures are hated for, often depending less on what they’ve done (or believed), but how they presented it to the world. Lots of good conversation (or at least chin-scratching contemplation) fodder, as is usual with Klosterman.

One passage in particular jumped out as a good reason to turn the lens back on myself, especially in the shadow of recent events:

Clear, unsubtle satire on TV shows like SNL and The Daily Show and The Colbert Report can succeed as entertainment, but they unintentionally reinforce the preexisting world: These vehicles frame the specific power holder as the sole object of scorn. This has no impact beyond comforting the enslaved. Power holders — even straight-up dictators — are interchangeable figureheads with limited reach; what matters far more is the institutional system those interchangeable figureheads temporarily represent.

So what does this mean, outside of an academic discussion about power? Well, maybe this: If you want to satirize the condition of a society, going after the apex of the pyramid is a waste of time. You need to attack the bottom. You need to ridicule the alleged ideological foundation an institution claims to be built upon. This is much, much more discomfiting than satirizing an ineffectual prime minister or a crack-smoking mayor. This requires the vilification of innocent, anonymous, working-class people.

As happy as I am to see The Daily Show in particular continue doing good work poking the giant, it may be a way for me to go on feeling superior while laughing at those in power. I sit on my couch venting my frustrations through comedy, while they go right on running-slash-ruining the world.

Does satire ever actually change anything for the better, or is it just a way to feel better about what’s wrong with the world?

Which satires are the most effective? What would make others more so?

Are the biggest fans of satire the people that are actually doing the least to make a real difference in the world?

If your legacy is the people whose lives you reach, LOOK AT THAT LEGACY.

Jon Stewart took over The Daily Show in 1999, the year I graduated high school. (I was a fan even before, of the sillier Craig Kilborn version). Since then, I think I’ve barely missed an episode. In college, he was our nightly news, a break from studying. Since then — and my acquisition of a DVR — he became a dinnertime companion, watching his take on the previous day’s news over a meal, catching up even on the days we missed because his service was so invaluable.

His show made current events engaging, and more importantly made our problems palatable.Through the difficult Bush years, he offered catharsis. Through the bizarre upheavals of the Obama years, he offered a voice of reason. And always intelligence, always laughter.

Thinking about his departure, I don’t know if there’s a single other person in entertainment I’ve spent as much time with as Jon Stewart. (Maybe The Simpsons, but that isn’t quite the same.) Leading up to his final show, I felt a strange clenching in my chest. It wasn’t sadness, like you’re preparing for a loss. At least not only that. The closest comparison I can make is saying goodbye to someone you loved in high school. They’re always going to be a part of your life. In many ways they helped make you who you are. But now it’s time to move on, and you both know it. You may see each other again some day, but it’ll be different. But that’s okay. The time you had was unforgettable. Invaluable. And you leave with a little bit of dread, but also gratitude. Grief, but also joy.

Which celebrity have you spent the most time enjoying? Why them? How did they affect your life?

If any current celebrity suddenly went away, which one would be the biggest loss, the biggest blow to your life, would leave the biggest hole?

For me it’s Jon Stewart, and there might never be another one bigger.

Thanks Jon.