The disclosed gaming system, gaming device and method provide a game including a plurality of awards, each of the awards associated with a plurality of award characteristics, including an award value and a level of difficulty. Based at least in part on the award characteristics associated with the awards, a player strategically chooses which award or awards to play for (i.e., which award or awards to attempt to collect) in the game. In certain multiplayer embodiments, two or more players can work together to obtain awards.