"April is the cruellest month." We know Eliot meant it as a paradox: the month that's supposed to be the prettiest and most sensual is actually the worst, because as soon as the birds and bees start doing it again, everyone feels terrible about their own sex lives.
Still, let's be honest with ourselves. April is pretty. Nobody really has a grudge against April. You might as well say cake is the cruelest food: it sounds sophisticated, and your friends all nod and take another bite of kale salad, but at the end of the day you're stuffing your face with frosting.
All bullsh*t (to quote T. S. Eliot) aside, here's the worst the year has to offer. Click on each month for explanations: