Some information is factual (e.g., "Paris is in France"), whereas other information is probabilistic (e.g., "the coin flip will be a [Heads/Tails]."). We believe that good Language Models (LMs) should understand and reflect this nuance. Our work investigates this by testing if LMs' output probabilities are calibrated to their textual contexts. We define model "calibration" as the degree to which the output probabilities of candidate tokens are aligned with the relative likelihood that should be inferred from the given context. For example, if the context concerns two equally likely options (e.g., heads or tails for a fair coin), the output probabilities should reflect this. Likewise, context that concerns non-uniformly likely events (e.g., rolling a six with a die) should also be appropriately captured with proportionate output probabilities. We find that even in simple settings the best LMs (1) are poorly calibrated, and (2) have systematic biases (e.g., preferred colors and sensitivities to word orderings). For example, gpt-4o-mini often picks the first of two options presented in the prompt regardless of the options' implied likelihood, whereas Llama-3.1-8B picks the second. Our other consistent finding is mode-collapse: Instruction-tuned models often over-allocate probability mass on a single option. These systematic biases introduce non-intuitive model behavior, making models harder for users to understand.