Windows Destruction is a series of streams created by Joel, in which he destroys Windows (and sometimes other) computer Operating Systems using a virtual machine, downloading all kinds of viruses and malware onto them (includes some gameplay of WildTangent OEM games), and generally dicking around until the system can no longer boot. The series gets a lot of attention on Joel's channel, and he even posts the full streams of Windows Destruction on his Full Stream YouTube channel.
The Red Star OS Destruction is (as of now) the official Linux Destruction.
Joel is noticably nervous during this Destruction. He mentions that, prior to the stream, he was advised not to hook the OS up to the internet but did so anyway. Given North Korea's reputation in the modern world, It's possible he was genuinely concerned for his safety and privacy.
The Windows XP Destruction gave birth to the memes Bonzi Buddy and Kup Teraz.
The Windows 7 Destruction gave birth to the Softonic meme.
In the Windows 8 Destruction, Joel prank calls PC Optimizer Pro, an Indian scammer company selling fake software to anyone not well-informed enough to buy it.
Joel has mentioned that some of the jokes he made during this segment, in particular the "Attack Helicopter" joke, did not age well. He has apologised on his Tumblr, stating he never meant it as an insult to the LGBTQ+ community and was just messing with the person on the other end of the phone.
The Windows Vista Destruction gave birth to the Protegent meme.
Some of the staples of the Windows Destruction series are that Joel likes downloading songs in a MIDI format and setting his desktop to a low quality picture.
Starting with Windows Vista eMachines OEM. they had this.