Here's a paper I'll be presenting in November: Modeling Meaninglessness: The Uses and Abuses of Sisyphus
Abstract: Sisyphus’s futile stone-rolling is often presented as a paradigm of meaningless activity. Recent philosophers often suggest variations on the Sisyphus example as a way of identifying what changes would make his activity meaningful. However, imagining Sisyphus’s activity without reference to its mythical context or to the complexities of Sisyphus’s psychology (beyond his first order desires) renders his situation practically incoherent and inhuman. If we are seeking an account of meaning in human life through reflection on Sisyphus, then we need to imagine him—and other such exemplars of meaning and meaninglessness—in greater detail.