I'm a huge comedy and intellectual fan of Oswalt. This article has some great insights on him, finding the right career and a nuanced comedian-view on Daniel Tosh's rape joke.
(quote from the article... which I can't seem to format)
"Daniel Tosh was trying to see if he could make rape funny. He was failing. You're allowed to do that at an open mike. This woman got angry and interrupted him before he could get to the point he was making. She was wrong for doing that. But he was wrong because he had been trying to kick upward at this terrible thing—rape—but then he kicked downward by saying about this drunk woman, "Wouldn't it be funny if she got raped by five guys?" You always have to consider who is the victim and what is the context. Sarah Silverman joked, "I was raped by a doctor, which is so bittersweet for a Jewish girl," and she's come onstage to music saying, "Oh, I was raped to that song." Is she a misogynist? If you listened to only part of a Lenny Bruce bit, you'd say, "He's a racist." But if you had waited three more minutes, you would have seen he was horrified by racism and was finding new ways to make a run at the subject."