Shortly before his death in 1995, Kenneth B. Schwartz, a cancer patient at Massachusetts General Hospital (MGH) founded The Kenneth B. Schwartz Center at MGH. The Schwartz Center is a nonprofit organization dedicated to supporting and advancing compassionate health care delivery, which provides hope to the patient and support to caregivers and encourages the healing process. The center sponsors the Schwartz Center Rounds, a monthly multidisciplinary forum where caregivers reflect on important psychosocial issues faced by patients, their families, and their caregivers, and gain insight and support from fellow staff members. The diagnosis of cancer is incredibly stressful, and treatments are arduous. Humor may help to ease the pain, show the human side of the health care team, and help everyone cope. Whether the patient uses humor to lighten the mood of a difficult consultation with their physician, or health care workers use it to help cheer each other through the day, humor and laughter can be valuable tools. Humor can soften the isolation experienced by both patients and staff. When used sensitively, respecting the gravity of the situation, humor can build the connection among the caregiver, patient, and family. However, insensitive joking is offensive and distressing, and experience suggests a variable acceptance of humor by patients with life-threatening illnesses, making humor a high-risk strategy, and it can be a pejorative maker of an adversive power differential. The medical literature contains little on humor, and very little research has been conducted on this common aspect of human communication. Through an examination of physician and nurse experiences, the role of humor in medicine is reviewed.