First, it's hard for people to get past the bombast. That's understandable. In just the above interview alone he calls himself the "Michael Jordan of music" and the "Steve [Jobs] of the internet." Yes, it's distracting when he talks about his legacy among the all-time greats while he's still alive. But that doesn't mean it isn't true. If Jordan had said while he was playing, "you know, I think I'm one of the greatest players of all time," people woulda hated on him, too. But now that he's retired people can all safely agree that that is undoubtedly true.
Second, I think Kanye has a point with all his award-show rants. Ye points out that neither Dark Twisted Fantasy nor Watch the Throne was nominated for album of the year, and he made those in the same year. RIDICULOUS, and not in the "word most often used to describe Kanye" way. He also points out that he has never won a Grammy when a White-person was nominated. From the interview: "I really appreciate that I was able to win rap album of the year. But after awhile it's like, 'wait a second. This is a setup'." Don't think that's wrong.
Third, he's incredibly self-reflective. That might be self-evident from someone who admits that they are "synonymous with vanity," but he realizes that he has a pulse on pop like few ever had. It's inspiring to hear him reminisce that he knew he was gonna be a star when we wrote "light-skinned friend look like Michael Jackson." He knows where the culture is, what will connect with them, and how to engage them ("we want pre-nup" x2).
People think it's laughable that 'Ye said he's the "Bob Dylan of my generation," but what's laughable is our generation, not that Kanye represents the zeitgeist. Bob Dylan was the voice of the 60s, a time of intense cultural upheaval and social change. So far the 00s have been about the first Black President and Twitter. Which is cool. But you can be the voice of this generation without saying a lot. Most of what we will be known for is the eradication of privacy, both voluntarily (Facebook) and passively (NSA).
People balked at his Katrina moment, too, when he said on a live TV telethon that "George Bush does not care about Black people." At the time, my reaction was mostly like Chris Tucker's ("I can't believe he said that."). Now I think that it's brave. In an era when President Obama's Secretary of Defense can laugh at an Indian-American Professor by asking him if he's a member of the Taliban, callin people out is both legitimate and necessary.
Maybe in the end the right analogy is not Michael Jordan or Steve Jobs, but Andy Warhol. With the release of Yeezus, Ye continues to own what the Times rightly calls "the most sui generis hip-hop career of the last decade." I would take out the qualifier "hip hop" and extend the time period. Warhol, the year before he died, painted "The Last Supper cycle," in which he made "almost 100 variations on the theme," which the Guggenheim felt "indicates an almost obsessive investment in the subject matter." Kanye is not ridiculous. He's obsessed.