Trivia CD-ROM game for teenagers for Windows 95/98/ME/2000/XP. Features Phil Ridarelli (voicing Schmitty) as the host. The online portion no longer works as of 2020, but you can still do a local home play with up to three players on the same computer.
You Don't Know Jack 5th Dementia is incompatible with Windows 10; it wouldn't show the game upon launch, not even when I turned off my internet connection before I tried it.
On a side note, it does run under a Windows 98 virtual machine using Microsoft's Virtual PC 7 on a Power Mac G4 (MDD 2003) running Mac OS X 10.2.8 (Jaguar), although the game is not designed to run under emulated systems due to some complex DirectX instructions, YDKJ 5th Dementia will run slowly and the sound starts to glitch a lot! Your mileage may vary when running the game under other virtual machine software and operating system combinations.
P.S. This is the first You Don't Know Jack game to be Windows-only, dropping support for the Classic Mac OS.