1. Jumping off the Tribune Tower.
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I would do this at night, while wearing a long black cape ala Batman in the first movie. When I dive off one of the flying buttresses at the top, I will be humming a spirited rendition of the Batman theme (dum-dum-dah-dum-da!).
2. Vienna Beef Overdose and Swan Dive.
I would begin the evening by eating about five cans of those Vienna sausages, as an appetizer. I've always loved those disgusting sausages, even though their meat content is dubious at best, and they're packed in that disgustingly gelatinous and organic looking mucus. Ahh, the perfect bachelor food.
After eating my sausages, I would then hop in a cab and direct the driver to take me on a very specific route to predetermined Vienna Beef stands all over the city. I will gorge on hotdogs, hamburgers, gyros and all things fried until I'm about to puke. Then I'll gorge some more.
The final destination in this scenario to take me to the ultimate final destination is the actual Vienna Beef processing plant on North Damen. Well, the bridge facing the factory at least.
I will have the cab driver take me to that cool red bridge spanning the river on the west side of the plant. I'll literally roll my bloated body and distended belly out of the cab. In one last Herculean effort, I will climb onto the railings and prepare for my last spectacular display. Once situated, I will shove my finger down my throat and spew a glorious meat by-product fountain in honor of the great meat processing plant before me. I will give back to nature what Vienna Beef had given to me. Just as the meat-product-vomit-fountain frothing from my gullet reaches its apex, and just before it begins to wane, I will swan-dive off the bridge, following the Vienna trail into the river.
3. Vandalizing Mayor Daley's House and/or Millennium Park.
If I am not killed in either of these scenarios when first committed, then as a soon as I get out of jail, I will immediately undertake the second vandilization, thereby ensuring that I die.
I don't want to throw toilet paper in Daley's trees or eggs at his house, oh no. Instead, I want to steal a large bulldozer and use its rear-ripper to carve large X'es into Mayor Daley's lawn. This will be done to his house and the open fields in Millennium Park, especially Pritzker Pavilion. I will begin this project under cover of night. When the cops try to arrest me, I'll explain through the bullhorn that I brought along that I have plans to redevelop the land (perhaps an airport?). When I fail to stop ripping up Daley's lawn and/or Millenium Park, they will have no choice but to take me out with a well aimed bullet.
4. Drive through Humboldt Park blasting Lawrence Welk music.
5. Sodomize the Harry Carey Statue Outside of Wrigley Field.
In this situation, I would simply climb on top of the statue's podium, shortly before the end of a ball game. I'll stand about here:
Then, when the drunken fans are streaming out of the stadium, I will commence sodomizing Harry Carey here and here:
Finally, if I'm not torn off the statue and beaten to a bloody pulp after a few moments, I will start:
No, I haven't gotten much work done today. . .