English professors still love to quote The Waste Land, "April is the cruelest month," especially professors who teach on a semester-system that ends in early-to-mid-May. Another year of academia is ending, another semester is ending, acute senioritis has set in (and the rest of the students are antsy, too), and just when everyone on campus thinks her or she can't do one more thing, five more things get scheduled. So if you hear an English professor mutter this phrase, he or she is doing so not merely to sound pretentious.
In the upside-down world of The Waste Land, regeneration can be a bad thing, so that's one reason one voice in the poem asserts that April is the cruelest. In other parts of the poem, voices express yearning for regeneration that refuses to arrive.
But what, in fact, is the cruelest month?
When I was in grammar school, I probably felt as if November was the cruelest month because the days were dark and cold in the Sierra Nevada, playing outside was a brutal affair, and the 12-mile (one-way) bus-ride to school seemed awfully dreary.
When I was in late grammar-school, September was the cruelest month because summer was still pretty much one long holiday, and I could only just bear the thought of going back to school.
I rather enjoyed most of high school--the academic part was okay, I played sports, I had some good friends, and what wasn't to like about the young women? Also, I'd begun to work full time during the summer as a laborer, first at a gravel-plant, then as a carpenter's helper/hod-carrier, so June became the cruelest month; gone were the sunny afternoons after class when I could just hang out with friends when classes were done. (I gave up baseball after my sophomore year, so after basketball season was done, I didn't have a practice to go to.)
Once I got to college, I don't think any one month was the cruelest. I seem to remember liking the summer-work as a laborer (I'd become more skilled, and I liked making that cash), and after I turned 21, I could work 8 hours during the day and either go fly-fishing in the evening or go to one or both bars in town, and I do remember feeling some dread in early September, knowing I'd have to head back to college, hit the books in a Ph.D. program (which did not seem to be pointing directly at employment; almost every job advertised by the MLA, anywhere in the country, drew 200+ applications), and teach one freshmen-writing class per quarter. I knew I didn't want to be a laborer the rest of my life (labor is a young person's game), but it was hard to beat working outside in the Sierra Nevada, living near trout-streams, and being able to drink in funky rural bars).
Now, I think November is back at number one on the Cruel chart. Gloom descends on the Pacific Northwest, and rain settles in. In our first year in the Pacific Northwest, it rained every day that November (we know because we counted), and it seemed to get dark at 2:00 p.m. Also, the flu virus for which we are unsuccessfully vaccinated each year (they must just shoot sugar-water in our veins) seems to get busy in November.
Pacific Northwesterners tend to loathe June because it can behave very badly and be cloudy and cold--at a time when everyone feels entitled to summer. July, August, September, and even a big hunk of October can he heavenly up here, however.
I think any time you're out of work makes for a bad month. I tend not to say "April is the cruelest month" because I feel lucky to have a good job, especially when the price of gasoline (a price that must devastate most working folk) and food are rising so fast.
I've never been a big fan of March, and I don't ever remember disliking January. "March," I think, is a dumb name for a month, whereas "January" sounds pretty good. Sure, it's cold in January, in the Northern hemisphere, in most places, but at the same time, January never lied to anyone and said, "I promise to be warm and sunny." January just goes about its business, which is to be cold and icy but to start lengthening the days. Back in the day, I remember wanting the professional golfer Don January to win a tournament because I thought his name was cool.
May the month of May treat you well.