My sons love to play either Life or Monopoly. When they were younger it was Trouble or Snakes and Ladders. We have a family night where we either play board games, or watch a video together.
We like to play word games. Upwords is a good one that's easier for younger children to play than Scrabble. It's been awhile since we played Pictionary, but that's another game we like. I guess I have a sentimental attachment to Monopoly since that's the main game we played as a family when I was growing up.
My kids enjoy Snakes and Ladders. It was their favorite game since they were little and they couldn't seem to outgrow it just yet My wife and I like Pictionary and Boggle best because just like Ryan, these games are something we grew up with.
When the kids were little it was always Life or Monopoly, we have replaced those games at least 1/2 a dozen times. Broken pieces, missing cards and even a broken board or two. The wife and I still play a weekly game of chess too.
I used to enjoy a lot of board games with my family. We all played monopoly and Snakes and Ladders together. Unfortunately we don't play too many board games anymore these days with our own kids, but we do share a lot of activities together like swimming and volleyball.
We absolutely love Cooties. It is different every time you play and we try to make the craziest looking Cooties every time. My daughter is also getting into Operation these days so we play that a lot.