So yes, I've either guessed these clues, had to give these clues, seen someone give these clues, or gotten these as suggestions while reffing. Only two of them I modified from other suggestions (those are in italics), and only one of them is one that's been talked about but never actually performed (that's underlined).
Following our rules of ordering the 5 Things, they're also presented in the order we'd perform them in the game.
Again, like I said to the team in rehearsal, none of these are impossible. They are very, very intricate, and will require a lot of process, but they are not ungettable. I personally don't find anything entertaining in a completely impossible 5 Things. You want to see the struggle, and then you want to see the ultimate payoff. A 5 Things that is ungettable, and we never get to see any sort of triumph is just disheartening for everyone.
How would you get someone to guess these clues?
1.) Syncing an iPod to a Computer
iPod = Megalodon
Computer = H.G. Wells' Time Machine
2.) Voting a Bill into Law
Congress = (House of Representatives) Teddy Roosevelt's Rough Riders
(Senate) The Argonauts
When = Height of the Ottoman Empire
3.) Going on the Oregon Trail
Wagon = Leonardo da Vinci's Flying Machine
Hunting What = All the Star Signs of the Zodiac
Hoarding What = RegretThe guesser = Speaks in tongues
5.) Crashing a Party
Whose Party Was It – John Phillips Sousa
Where Is the Party Held – On a Peninsula