This is best boosted. The Live community for this game is dead. Look for a boosting partner or use 2 copies/Xboxes. Once you have one other person/Xbox follow this method:
Have the other person/profile in your party, start an Xbox Live game of Three And Out. Once you're in the game lobby, hit 'X' to invite the other person in the party then ready up and skip all the cutscenes.
Three And Out only penalizes you if you get the question wrong, but does nothing if you don't answer. Therefore wait until you see a question you definitely know the answer to and then answer it. You will have to answer the final question, and it is best to have a computer and Wikipedia, Google Maps, and a dictionary website.
This will take some time to boost with another party, but as long as you get all 10 questions right you only have to do 50 games total.