The single- and multi- processor cup games can be used to model natural problems in areas such as processor scheduling, deamortization, and buffer management. At the beginning of the single-processor cup game, $n$ cups are initially empty. In each step of the game, a filler distributes $1$ unit of water among the cups, and then an emptier selects a cup and removes $1 + epsilon$ units from that cup. The goal of the emptier is to minimize the amount of water in the fullest cup, also known as the backlog. It is known that the greedy algorithm (i.e., empty the fullest cup) achieves backlog $O(log n)$, and that no deterministic algorithm can do better. We show that the performance of the greedy algorithm can be greatly improved with a small amount of randomization: After any step $i$, and for any $k ge Omega(log epsilon^{-1})$, the emptier achieves backlog at most $O(k)$ with probability at least $1 -O(2^{-2^k})$. Whereas bounds for the single-processor cup game have been known for more than fifteen years, proving nontrivial bounds on backlog for the multi-processor extension has remained open. We present a simple analysis of the greedy algorithm for the multi-processor cup game, establishing a backlog of $O(epsilon^{-1} log n)$, as long as $delta$, the games other speed-augmentation constant, is at least $1/poly(n)$. Turning to randomized algorithms, we encounter an unexpected phenomenon: When the number of processors $p$ is large, the backlog after each step drops to emph{constant} with large probability. Specifically, we show that if $delta$ and $epsilon$ satisfy reasonable constraints, then there exists an algorithm that bounds the backlog after a given step by three or less with probability at least $1 - O(exp(-Omega(epsilon^2 p))$. We further extend the guarantees of our randomized algorithm to consider larger backlogs.