I don't usually play board-games, but when I do, Monopoly is on top. Having all the cards in Monopoly, while impossible, is highly based and I hope that one day when I play Monopoly I will successfully do it (although it would be hard unless there's like 8 players).
Thinking about it a bit more, Monopoly is a favorite of mine due to the fact it is literally me. Capitalism is based and I approve of it, which is why I LOVE Monopoly, it's just capitalism but a game so I don't lose actual money if I mess up XD.