Hey HN, I know video content is not the norm here, but I had to submit this.

Bookended by some semi-related absurdism and surrealist humor, this video is an hour-long (00:04:42 - 01:09:30) breakdown and analysis of music notation app Finale's journey from entrenched industry leader to dead and discontinued 35 years later.

It's a great primer on how software dies over time through poor design, management and engineering decisions, and what the slow-motion train wreck actually looks like as a software product collapses under its own weight.