Sometimes comedy illuminates hard truths with a pointed urgency that other means can’t quite achieve. Sometimes comedy is just funny. This series of posts is mostly about the former instances, but the latter is valuable, too.

Through my teenaged years, there were few television programs I was more devoted to than Late Night with David Letterman. Blithely disregarding the need to get a reasonable amount of rest so I’d be fresh for school in the morning (dumb ol’ school), I routinely stayed up to see one day cross into the next. I didn’t want to miss a single inspired moment. Of the recurring bits, I naturally had my favorites, including one that only came around once per year. I was especially careful to catch episodes that aired towards the end of October because I was desperate to be sure I caught the holiday-themed presentation dubbed “Late Night Presents: Halloween Costume Parade.”

It truly had everything I valued in a good Late Night comedy segment: absurdity grounded in snarky cultural observations, art direction and costumes that were simultaneously deliberately chintzy and ingenious, tremendously precise language (“Here’s a costume from the fantasy world of trash and rubbish”), and an element that was sure to make Letterman a little exasperated. (On that last point, in the video below, when he joking tells one kind “Don’t make trouble,” he kinda means it.) Knowing the procession of delightful disguises wouldn’t crop up again until the calendar allowed it somehow made the laughs that much more satisfying.

Previous entries in this series can be found by clicking on the “Laughing Matters” tag.