Some comedians have been complaining about cancel culture and an inability to make the jokes they want, but Maron isn’t having any of that and his special is a testament to riding the edge between the funny and the profane. Early on he makes a crack at the expense of such comedians, saying that “anti-woke” comedians all just want to say their version of the same three things, pointing out that many of these comedians aren’t broke and jobless because they’re being censored, it’s just that they’re not funny. To nail the point home, Maron makes jokes about the Holocaust, euthanizing your own child like you would a family pet, and his final moments with his dead girlfriend — he pushes the boundaries of what’s acceptable to joke about but it’s never bigoted, reactionary, or lazy. A lot of “offensive” comedians like to say that they’re just being honest, but Maron really is, even if that honesty is genuinely shocking. 

Shelton’s death is the specter that haunts “From Bleak to Dark,” metaphorically (and perhaps literally), and the resulting grief and surviving that grief inspired much of the special and helped Maron solidify his love of comedy:

“[After Shelton’s death] would I ever be able to be funny about things? […] humor that comes from real darkness is really the best because it disarms it. It’s elevating to the spirit. It’s why I got into comedy because I would watch comics and they would take things that were complicated or horrifying and simplify them and sort of make you see them in a different way and have a laugh.”

This thesis is important to remember as the jokes get darker and Maron truly tests the edge of morbid humor because it is extremely cathartic.