Why does humor in the workplace sometimes have magical effects and at other times is disastrous? The answer is not as simple as “some jokes are better than others,” or “some people are funny while others are not.” The reality is that injecting light-hearted remarks into professional interactions always entails risk. Guidance on when that risk is worth taking and might in fact lead to great rewards can be derived from analyses using artificial intelligence (AI) and natural language processing on data from one of the most emotionally charged professional settings: health care.