What if we could get Bob Dylan to interview Michael Bloomberg? Now we can! Sort of. Questionizer does simple natural language processing on two texts, looking for questions and answers in each. Then it takes questions from one text, and answers from another. I fired it up on some Dylan lyrics and a recent Bloomberg interview. Let’s see what happens:

Dylan: Yes, and how many seas must a white dove sail before she sleeps in the sand?
Bloomberg: Zero.
Dylan: Yes, and how many times must the cannon balls fly before they're forever banned?
Bloomberg: What’s one thing got to do with another? Spitzer’s case—it’s probably more name recognition and Stringer’s lack of it. With De Blasio, the percentage of the public that’s going to elect him is pretty small. And he doesn’t have any ideas. “I’m gonna raise the taxes.” You know that Albany, under no circumstances, nor the governor, under any circumstances, is going to allow that! So come up with some real ideas, Bill! Stop-and-frisk has also been a big issue.
Dylan: How many years can a mountain exist before it's washed to the sea?
Bloomberg: I don’t know. I think that if crime starts tweaking up the tiniest bit, there’s going to be enormous pressure. And there may be other ways to do it—we’re not the only ones with good ideas, but we’ve found a formula that works and we believe is consistent with the law.
Dylan: Yes, and how many years can some people exist before they're allowed to be free?
Bloomberg: The judge is just wrong. We have not racial-profiled, we’ve gone where the crime is. I don’t have any doubts that she will be reversed right away.
Dylan: Yes, and how many times can a man turn his head pretending he just doesn't see?
Bloomberg: I cannot get involved in the next administration, nor should I. But for something like that I would certainly make my views known.
Dylan: How many times must a man look up before he can see the sky?
Bloomberg: The sad thing, which nobody’s willing to talk about, is that most of our crime is in two neighborhoods: southeast Bronx, central Brooklyn. All minority males 15 to 25. We’ve got to do something about that. And unless you get the guns out of their hands, you’re not going to ever be able to do anything.
Dylan: Yes, and how many ears must one man have before he can hear people cry?
Bloomberg: It is very difficult to explain complex things in sound bites. And government talks to its constituents generally through the press, whereas private-sector organizations talk directly to their customers. If you have something that is complex and long-term before you see results, and there’s one or two people who are willing to go on the record and say the reverse, it is very difficult. Particularly in the days of social media, when there’s an instant referendum on everything—I think it’s going to make governing more difficult.

The Questionizer code can be found on GitHub. It was written in Python, and natural language processing was provided by NLTK.