Rollout algorithms have demonstrated excellent performance on a variety of dynamic and discrete optimization problems. Interpreted as an approximate dynamic programming algorithm, a rollout algorithm estimates the value-to-go at each decision stage by simulating future events while following a greedy policy, referred to as the base policy. While in many cases rollout algorithms are guaranteed to perform as well as their base policies, there have been few theoretical results showing additional improvement in performance. In this paper we perform a probabilistic analysis of the subset sum problem and knapsack problem, giving theoretical evidence that rollout algorithms perform strictly better than their base policies. Using a stochastic model from the existing literature, we analyze two rollout methods that we refer to as the consecutive rollout and exhaustive rollout, both of which employ a simple greedy base policy. For the subset sum problem, we prove that after only a single iteration of the rollout algorithm, both methods yield at least a 30% reduction in the expected gap between the solution value and capacity, relative to the base policy. Analogous results are shown for the knapsack problem.