Trivial Pursuit

This has to be done in Fact & Friends mode (you can add a 2nd player from the same controller). When it's P2's turn, you'll get the chance to bet if they'll get it right or wrong. (don't choose the 'I Know It!' option as it won't count as a bet). If you're controlling P2 then it's easy to make them go the way you want. Get 5 correct bets for the achievement, doesn't need to be consecutive so don't worry if you get one wrong.