Apples to Apples: a simple, yet clever word association game.
At first I thought it was a silly game. But DS & DW both enjoyed it and convinced me to give it a go. While it might be better with a couple more people, we make the best of our little nuclear family. In fact, our DD4 acts as the "judge," which in itself leads to humorous results, and gives her an active role.
Monopoly -- the perennial favorite in our family for three generations. DS took to it right away and is able to sit for full-length games.
HOWEVER, there are SOME children in this world who do not appreciate landing on Boardwalk+Hotel -- AT ALL. He stormed off to his room while the banker mortgaged all his property in an effort to pay the rent. He was still short by a bunch. Sadly, and despite his pleas for mercy, he was forced into Bankruptcy @ the tender age of 7.
That extended drama caused the game to be "shelved" for a couple months.