Man, I need to finish watching those Tabletop episodes :P The last time I tried I had some internet issues, and couldn't get them to load. Anyway, I'm glad that people are interested in trying the game out; it can definitely be a lot of fun.
I'm curious to see what setting you have in store! Well, that's the thing; we'll be choosing the playset together :). There are four playsets that come with the Fiasco book, and another couple that come with the Fiasco companion, but there is also a large collection of free playsets available on the official website. There is really quite a diverse set of options, including: suburban America, touring rock bands, an Antarctic research station, a group of dysfunctional fantasy heroes, a parody of tabletop gamers, an official Paranoia playset, people stranded on an island, and many, many more.
Each of these playsets helps set the mood and theme for the game, but each set is very replayable as well. If you saw the setup episode of Tabletop, you'll see what I mean. For example, the 'stranded on a desert island' playset (No Luck Atoll) could easily end up creating something like Lost, Gilligan's Island, or even the TV show Survivor.
Fiasco works best when everyone involved knows the playset's genre and is enthusiastic about the types of stories that are produced in that genre.
If no one has a playset that they really want to play, I'll provide two or three good beginner playsets, and we can choose from there.