In the classical multi-armed bandit problem, instance-dependent algorithms attain improved performance on "easy" problems with a gap between the best and second-best arm. Are similar guarantees possible for contextual bandits? While positive results are known for certain special cases, there is no general theory characterizing when and how instance-dependent regret bounds for contextual bandits can be achieved for rich, general classes of policies. We introduce a family of complexity measures that are both sufficient and necessary to obtain instance-dependent regret bounds. We then introduce new oracle-efficient algorithms which adapt to the gap whenever possible, while also attaining the minimax rate in the worst case. Finally, we provide structural results that tie together a number of complexity measures previously proposed throughout contextual bandits, reinforcement learning, and active learning and elucidate their role in determining the optimal instance-dependent regret. In a large-scale empirical evaluation, we find that our approach often gives superior results for challenging exploration problems. Turning our focus to reinforcement learning with function approximation, we develop new oracle-efficient algorithms for reinforcement learning with rich observations that obtain optimal gap-dependent sample complexity.