Conan O’Brien is great. His work on Late Night, following David Letterman’s departure in 1993, brought a new and youthful energy to the show that resonated deeply with America’s aspiring funny people. Also, The Simpsons. Also, Saturday Night Live. Also, Conan. Also, that episode of Andy Richter Controls The Universe where he told Andy that he’s got “a good honest smell. Like potatoes.”
We won’t likely get a chance to meet Mr. O’Brien when he, Ron Funches, James Veitch, Taylor Tomlinson, and Flula Borg come to Milwaukee’s Riverside Theater on November 30, but we thought we’d assemble the questions we’d most like to ask him about our beloved city anyway. In no particular order, here are those questions. Enjoy.
1. What’s your favorite childhood memory about Milwaukee?
2. What’s your favorite Michael Crichton novel about Milwaukee?
3. What’s your least favorite Kathy Bates movie about Milwaukee?
4. What is your biggest complaint about Bob Uecker?
5. If Milwaukee called your home in the middle of dinner, how would you respond?
6. How would you rate Milwaukee on a scale of 1 to 10, with 1 being “1997 Chrysler LeBaron with high mileage and significant body damage” and 10 being “Peanut Butter Cap’n Crunch that’s been sitting out for 90 minutes”?
7. How does the cost of vacuum repair in Milwaukee compare to that of your hometown?
8. Have you ever heard of Milwaukee?
9. If Milwaukee was a 17th century mathematician, who would it be and why?
10. If Milwaukee was a 14th century mathematician (excluding Thomas Bradwardine), who would it be and why?
11. Do you ever wonder if Milwaukee has a secret identity, and if so, what city do you think has been pretending to be Milwaukee all this time? Is it Pittsburgh? It’s Pittsburgh, isn’t it? What makes you think Milwaukee’s secret identity is Pittsburgh, Conan?
12. How many people do you think should live in Milwaukee?
13. If people started replacing the word “million” with “Milwaukee” when talking about money, the same way they replace “thousand” with “grand,” as in “Aaron Rodgers makes over $30 Milwaukee per year,” do you think that would sound cool or not really?
14. What time do you think people in Milwaukee should get up in the morning?
15. Is it bad that Milwaukee doesn’t know how to change a tire?
16. When Milwaukee comes on the radio, do you typically listen or change the station?
17. If Milwaukee was a wide receiver on the 1999 New England Patriots, do you think that would change the way you view football?
18. If Milwaukee was a baked potato topping, what would it be?
19. Where would you move Milwaukee if it was on wheels and you could put it wherever you want?
20. If they made a giant barbell, big enough for everyone in Milwaukee to hold at once, how much do you think Milwaukee could bench?
21. If Milwaukee nicked itself shaving and showed up to lunch with a toilet paper corner still stuck to blood on its face, would you mention it right away or just wait, hoping that someone else will mention it?
22. When you’re in Milwaukee, do you experience feelings of dizziness or nausea?
23. If Milwaukee has seven cookies and gives one each to three friends, then buys four more cookies and gives one each to six friends, are the cookies oatmeal raisin or peanut butter? (Trick question: They’re chocolate chip cookies with walnuts.)
24. Should Milwaukee get a haircut?
25. If Milwaukee was in the market for a new lawnmower, and we’re not necessarily saying that it is, do you think it’s worth spending the extra money to get a self-propelled model? Milwaukee isn’t getting any younger and there are definitely some hills to deal with. A riding mower seems totally out of the questions, but honestly, maybe that’s even in play here. What do you think?