In 2013, the congressman I was working for agreed to participate on the Colbert Report's "Better Know a District" segment, in which Colbert asked congressmen and women ridiculous questions and got them to say embarrassing things. I was tasked with helping to prepare my boss for the appearance. Here's how I did that
  1. I watched hours and hours of "Better Know a District" clips and ranked representatives by how well and poorly they did.
    These videos gave me a good idea of the kinds of questions Colbert would ask and the buttons he'd press to make good TV
  2. I outlined the general structure of these segments, the questions my boss would definitely be asked, and the areas Colbert would likely hit on.
    My boss was from Wisconsin, gay, and a magician. All these things were going to come up. I should say here this congressman was one of the best people I've ever worked for. I respected him dearly and wanted to be his best friend. He did a magic show for me on my last name.
  3. Then we held several early morning, hour-long prep sessions
    We over-prepared. Probably cause it was so fun.
  4. These sessions went like this: ask the congressman the most ridiculous, offensive questions we could, assuming the Colbert persona of conservative, oft-outraged interviewer. The point was not to predict the questions Colbert would ask, but to prepare the congressman to dance around a ridiculous/comically offensive question.
    There was a strict "no firing staff members" policy during these sessions
  5. Here are some of the questions I asked:
  6. Are Liberace and Harry Houdini your personal heroes, being a gay magician?
  7. Your state is home to heroes such as Paul Ryan and Joe McCarthy. How ashamed would McCarthy be of you?
  8. Your district represents Madison. Tell me a little about our fourth President James Madison.
  9. You are known to have an expansive collection of Bob La Follette memorabilia. La Follette adamantly opposed US entry into World War I. Do you also support letting unchecked imperialist forces run rampant over West and Central Europe? Are you also a friend of the Kaiser?
  10. You're gay. When did you make that choice?
  11. Do you ever get lost in Paul Ryan's blue eyes?
  12. Who's your favorite member of Congress to brunch with?
  13. Which female member of Congress would you choose to act as your beard?
  14. Kill, Marry, Fuck: Paul Ryan, Scott Walker, Ronald Reagan. Gun to your head you have to answer.
    I said "sleep with" instead of fuck. This was a congressman after all.
  15. Who do you want to win this season of RuPaul's drag race?
  16. At the age of 14, you were named Wisconsin's top junior magician. In what other ways are you a trickster?
  17. If you're such a good magician why can't you make American jobs appear?
  18. What's your fave cheese?
  19. Why are cheeseheads a thing in Wisconsin. Is it cause the people of Wisconsin have the mental dexterity of a slab of congealed dairy?
  20. You support the legalization of marijuana. Are you high right now?
  21. Who is your dealer?
  22. Who in DC most needs to get high?