Although it may not really fit what you're looking for, there was a one-hour video linked here a few days ago that critiziced the entire modern desktop GUI landscape.
After I watched his videos I thought the same thing. Almost every big piece of software would benefit greatly from a Tantacrul-like teardown, but I also realize that such a thing would require a whole heap of real-world domain knowledge and possibly hundreds of hours of use to track down all the issues so thoroughly.
Only tangentially related, but EEV Blog recently did a video on PCB design BOM (Bill of Materials) optimization where he took a random open-source project as a counter-example.
I'm not an electrical engineer, nor do I design PCBs, but it was still pretty interesting if you're into that sort of critique.
