Mark's #9: Fast Food Franchise
If you like Monopoly at all, you owe it to yourself to hunt down a copy of this OOP gem by Tom Lehmann. Heck, even if you don't like Monopoly, you need to try this brilliant re-imagining of a classic real estate roll'n'move. Fast Food Franchise works like a charm with 2-5 players, it has a nice story arc, and has ample opportunity for smart play while still preserving the luck of the dice. I'm a huge fan - if you can't tell! :-)
BTW, this is the last game on my personal Top One Hundred that isn't also on the "official" One Hundred list.