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I think with advances in computational humor it might be possible to come up with some pretty funny headlines. Could be a fun weekend project with NLTK. https:

• awaisathar 8y ago
  "In 1966, Marvin Minsky at MIT asked his undergraduate student Gerald Jay Sussman to ±spend the summer linking a camera to a computer and getting the computer to describe what it saw². We now know that the problem is slightly more difficult than that." (Szeliski 2009, Computer Vision) :)
  • newman8r 8y ago
    Generating punny headlines from input text might be difficult, but maybe not. I'm not sure if anyone's specifically attempted that, most of the efforts I've seen have more to do with summarization. A lot of puns are pretty formulaic though so it might not be all that difficult.