4. "Is this a regular columnist spot (weekly, etc.)?"
No. We don't have a regular schedule for columnists; we just have a pool of writers who submit pitches for columns as they occur to them. If you're part of that team, you can submit as often as you want. If you have one great idea a week, then congratulations, you're weekly!
5. "What kind of columns do you publish?"
Commentary on pop culture, other fairly lighthearted nonfiction subjects, personal stories/anecdotes, and the like. But we'll listen to any suggestions, as long as they're based on real information, observations, or opinions. Here are some recent successful columns:
Note that we do not do satire, parody, or fiction. So no Onion- or Reductress-style satire. That means a Cracked columnist needs to have some research skills in addition to being able to make people laugh.
If that sounds good to you, or you know someone who'd be perfect for it, email firstname.lastname@example.org.