How would you approach it? Serious question.
When celebrities die, we often hear stories about their insecurities, sometimes to ridiculous degrees. It seems to affect artistic professions significantly, including your example of comedians. While I'm sure it also happens to accountants, bakers, and landscapers, and while publicity is definitely a lesser part of their professions than actors and musicians, I really think there's something that makes it more prevalent/common to the personalities that are involved in the arts.