“I’m trying to grow my fan base beyond women who brought a knife to prom,” the comedian Chris Fleming says at the start of his first HBO special, shot in Chicago. Massachusetts-raised and now Los Angeles-based, Fleming’s standup is a singular blend of physical comedy, pop-culture references, sporadic screaming, elevated vocabulary, and flashy women’s clothing. “There is a theory that these are just manic episodes,” he tells me. Fleming’s new special, thankfully, does little to dispel that notion. Did I mention he now ends his sets in song? —Carolina de Armas