Medical decisions, including physicians’ prescribing behaviors, are shaped by a complex interplay of clinical and nonclinical factors. We aim to determine how physician, patient, and relationship characteristics influence physicians’ decisions to accommodate brand-name prescription drug requests. We applied multivariate logistic regression to data from the Attitudinal and Behavioral Effects of Direct-to-Consumer Promotion of Prescription Drugs physician survey. We used a national probability sample of 500 primary care and specialty physicians reporting on a clinical encounter that involved a prescription drug request. Independent variables include physician’s assessment of the patient’s understanding of risks and benefits of a requested medication, whether the patient had the condition the drug treats, duration of the clinical relationship, and physician’s age, area of practice, years of experience, and gender. These variables were used to predict whether the physician prescribed the requested drug. Physicians were more willing to accommodate requests when they believed that patients had a clear understanding of the drug’s risks and when patients had the condition the drug treats. Primary care practitioners, compared to specialists, had higher odds of prescribing a requested drug. We conclude that clinical and communicative factors shape physicians’ decisions to prescribe requested brand-name drugs. Findings offer insight into the influence that direct-to-consumer advertising can have in medical encounters, and may guide efforts to enhance physician–patient communication and shared decision making.