There’s more than a passing resemblance to Norm Macdonald’s “make the setup and the punchline identical to each other” philosophy in Benjamin’s humor, the idea that something is funny just because it is, and you shouldn’t need to have a follow-through that makes the first part come to life. The difference between them comes from Benjamin believing honesty can be funny. One of his later stories of doing comedy in New York involves a time when he was part of a duo called Mike And Jon, and decided it would be funny to hire two male escorts to take the stage in their place and perform sex acts to music. As with that bit itself, the act of just telling the story is the joke, here in service of a larger narrative about how he failed to ride a motorcycle. The humor is the delivery, not the conclusion.


Benjamin folds every tale of shame, error, or woe into the overarching premise of failure, but within each are nested layers of other failures, such as how his inability to pretend like he was playing catch with his father, thereby not looking like a sad loner, is simply a prelude to his sitting quietly alone in a friend’s living room while he watches burglars steal the family’s possessions. A story recounting his failure to star in a low-budget porn is packed with preludes of other failures, like being hired to build a series of shelves one summer as a teen, only to realize he had no idea how, and rather than telling anyone, just spending the time by himself listening to the radio, doing nothing.

Admittedly, it’s tough to read Failure Is An Option without hearing Benjamin’s signature voice in your head, good-naturedly recounting everything that unfolds. But even the near-non sequiturs sprinkled among the chapters are incredibly funny, such as his transcription of a family that tries to communicate with a recently lost child through a medium who turns out to be misogynist, or page after page of “failed sexual positions.” (“The thinker: One lays flat on the edge of the bed while the other mounts from the top, facing out in sitting position, with one arm resting on the chin, appearing bored.”) What makes it all work, as with so much of his comedy, is the cleverly genial persona behind it all, undercutting potentially cruel moments and perpetually reminding the reader that even if a particular joke doesn’t work for them, that’s okay. Failing to laugh is just another example of his motto at work.